CN114409682A - Triazole pyridine receptor with positioning effect, polymer thereof and application thereof - Google Patents
Triazole pyridine receptor with positioning effect, polymer thereof and application thereof Download PDFInfo
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- CN114409682A CN114409682A CN202210133574.0A CN202210133574A CN114409682A CN 114409682 A CN114409682 A CN 114409682A CN 202210133574 A CN202210133574 A CN 202210133574A CN 114409682 A CN114409682 A CN 114409682A
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- pyridine
- dibromo
- triazolo
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- 229920000642 polymer Polymers 0.000 title claims abstract description 83
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 49
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 26
- 230000000694 effects Effects 0.000 title abstract description 12
- 230000005669 field effect Effects 0.000 claims abstract description 27
- 239000004065 semiconductor Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 14
- -1 borate compound Chemical class 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000003153 chemical reaction reagent Substances 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 26
- CSHCPECZJIEGJF-UHFFFAOYSA-N methyltin Chemical compound [Sn]C CSHCPECZJIEGJF-UHFFFAOYSA-N 0.000 claims description 24
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- NVDNDPFQAMUWFF-UHFFFAOYSA-N 4,7-dibromo-2-(5-decylpentadecyl)triazolo[4,5-c]pyridine Chemical compound CCCCCCCCCCC(CCCCCCCCCC)CCCCN(N=C12)N=C1C(Br)=NC=C2Br NVDNDPFQAMUWFF-UHFFFAOYSA-N 0.000 claims description 9
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 8
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- WDTOXRACOCNQRB-UHFFFAOYSA-N 2,5-dibromopyridine-3,4-diamine Chemical compound NC1=C(Br)C=NC(Br)=C1N WDTOXRACOCNQRB-UHFFFAOYSA-N 0.000 claims description 5
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001351 alkyl iodides Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000003541 multi-stage reaction Methods 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002474 experimental method Methods 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 230000005693 optoelectronics Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 238000000605 extraction Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000012512 characterization method Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000002484 cyclic voltammetry Methods 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- 235000003270 potassium fluoride Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 2
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CTJXBZHGMGKEIM-UHFFFAOYSA-N BrC1=CN=C(Br)C2=C1N=NN2 Chemical compound BrC1=CN=C(Br)C2=C1N=NN2 CTJXBZHGMGKEIM-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- INHYKPMJJAWZKY-UHFFFAOYSA-N trimethyl-[5-[4-(5-trimethylstannylthiophen-2-yl)-2,1,3-benzothiadiazol-7-yl]thiophen-2-yl]stannane Chemical compound S1C([Sn](C)(C)C)=CC=C1C(C1=NSN=C11)=CC=C1C1=CC=C([Sn](C)(C)C)S1 INHYKPMJJAWZKY-UHFFFAOYSA-N 0.000 description 2
- CZKXFGQEYYLUEK-UHFFFAOYSA-N 11-(4-iodobutyl)henicosane Chemical compound CCCCCCCCCCC(CCCCI)CCCCCCCCCC CZKXFGQEYYLUEK-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- FRUBQASVNDFUTD-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC2=NSN=C12 FRUBQASVNDFUTD-UHFFFAOYSA-N 0.000 description 1
- 241000338702 Cupido minimus Species 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical group C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a triazole pyridine receptor with a positioning effect, a polymer thereof and application thereof. The structural formula of the provided polymer is shown as a formula I. The Organic Field Effect Transistors (OFETs) prepared by taking the triazole pyridine polymer as the semiconductor layer have higher hole mobility (the highest is 9 multiplied by 10)‑3cm2V‑1s‑1) And has good application prospect in organic field effect transistors. Experiments prove that nitrogen atoms on pyridine have a positioning effect, and further research the application of the triazole pyridine (TP for short) receptors and polymers thereof in OFETs. The triazole pyridine polymer with the positioning effect further expands the variety of high-performance semiconductor materials, and has good application prospect in organic optoelectronic devices.
Description
Technical Field
The invention relates to a triazole pyridine receptor with a positioning effect, a polymer thereof and application thereof, belonging to the field of materials.
Background
Organic Field Effect Transistors (OFETs) are active devices which take pi-conjugated organic semiconductor materials as transmission layers and control the conductivity of the materials by regulating and controlling the current between source and drain electrodes through gate voltage. OFETs are key unit devices of organic photoelectric devices and circuits, have the advantages of simple device preparation process, capability of preparing flexible devices, large-area solution processing and the like, are expected to become next generation display and storage devices, and can be widely applied to flexible display devices and storages, such as foldable display screens, intelligent cards, radio frequency electronic tags, sensors, storages, large-scale integrated circuits, active matrix displays and the like in the future.
The material selected by the OFETs semiconductor layer can be an organic conjugated micromolecule material, and can also be a polymer film, so that the novel triazole pyridine (TP for short) receptor and the polymer thereof have important significance.
Disclosure of Invention
The invention aims to provide a Triazole Pyridine (TP) receptor with a positioning effect and synthesis and application of a polymer thereof.
The triazole pyridine polymer with the positioning effect further expands the types of OFETs materials, and has good application prospects in organic optoelectronic devices.
The structural formula of the Triazole Pyridine (TP) receptor with the positioning effect is shown as formula 1, formula 2 or formula 3:
in the formula, R is a linear chain or branched chain alkyl group having 1-60 carbon atoms in total.
The invention provides a preparation method of each compound, which comprises the following steps:
s1, reacting 2, 5-dibromo-3, 4-diaminopyridine shown in a formula 4 with sodium nitrite in an aqueous solution of acetic acid to obtain 4, 7-dibromo-2-hydrogen- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 5;
s2, in the presence of potassium carbonate, reacting 4, 7-dibromo-2-hydrogen- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 5 with iodoalkane to obtain 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6;
the chemical formula of the alkyl iodide is R-I, and R is a straight chain or branched chain alkyl group with the total number of carbon atoms of 1-60;
s3, in the presence of a catalyst I, carrying out one-step or multi-step coupling reaction on 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 and a methyl tin reagent of Ar1 or a borate compound to obtain a compound shown in a formula 1, a formula 2 or a formula 3;
the methyltin reagent or borate compound of Ar1 is selected from any one of the following compounds:
in step S1, in the aqueous solution of acetic acid, the volume ratio of water to acetic acid is 1: 0.5 to 5.0;
the molar ratio of the 2, 5-dibromo-3, 4-diaminopyridine shown in formula 4 to the sodium nitrite is 1: 0.5 to 4.0;
the reaction temperature is 10-40 ℃, and the reaction time is 2-60 hours;
in step S2, the molar ratio of 4, 7-dibromo-2-hydro- [1,2,3] triazolo [4,5-c ] pyridine represented by formula 5, the alkyl iodide and the potassium carbonate is 1: 1.0-2.0: 1.0 to 4.0;
the reaction temperature is 80-120 ℃, and the reaction time is 2-48 hours;
the reaction is carried out in N, N-dimethylformamide;
in step S3, the molar ratio of 4, 7-dibromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridine represented by formula 6 to the methyltin reagent or borate compound of Ar1 is 2: 0.9 to 1.1;
the molar ratio of the methyltin reagent or borate compound of Ar1 to the catalyst i was 1: 0.01 to 0.20;
the reaction temperature is 80-130 ℃, and the reaction time is 2-80 hours;
the reaction is carried out in the following solvents: at least one of toluene, chlorobenzene, and xylene;
the catalyst I is at least one of tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride and tris (dibenzylideneacetone) dipalladium.
Specifically, in step S3, the compound represented by formula 1 is obtained according to the following steps:
reacting 4, 7-dibromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 with 4, 7-bis (5- (trimethylstannyl) thiophene-2-yl) benzo [ c ] [1,2,5] thiadiazole shown in a formula 7 to obtain 4, 7-bis (5- (7-bromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridine-4-yl) thiophene-2-yl) benzo [ c ] [1,2,5] thiadiazole shown in the formula 1;
specifically, in step S3, the compound represented by formula 2 is obtained according to the following steps:
reacting 4, 7-dibromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 with (2-tri-N-butyltin) -thiophene shown in a formula 8 to obtain a compound shown in a formula 9, wherein the reaction proves that bromine atoms on one side, close to an N atom, of a triazolopyridine ring have higher reaction activity;
reacting 7-bromo-2- (5-decylpentadecyl) -4- (thiophene-2-yl) - [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 9 with 4, 7-diboronate-benzo [ c ] [1,2,5] thiadiazole shown in a formula 10 to obtain a compound shown in a formula 11;
reacting 4, 7-bis (2- (5-decylpentadecyl) -4- (thiophene-2-yl) - [1,2,3] triazolo [4,5-c ] pyridine-7-yl) benzo [ c ] [1,2,5] thiadiazole shown in a formula 11 with N-bromosuccinimide shown in a formula 12 to obtain a compound shown in a formula 2;
in the formula, R is defined as formula 2;
specifically, in step S3, the compound represented by formula 3 is obtained according to the following steps:
reacting 4, 7-dibromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 with 3,3' -difluoro-5, 5' -bis (trimethyltin) -2,2' -bithiophene shown in a formula 13 to obtain a compound shown in a formula 3;
the structural general formula of the triazole pyridine polymer provided by the invention is shown as formula I:
in the formula I, R is a straight chain or branched chain alkyl group with the total number of carbon atoms of 1-60, and n is a natural number between 5-100;
ar1 is the following group:
ar2 is the following group:
The triazole pyridine polymer provided by the invention can be specifically a polymer PTP-2TBTZ-TP-2FBT, PTP-2F4T-TP-BTZ or PTP-2FBT-TP-2 TBTZ;
the structural formula of the polymer PTP-2TBTZ-TP-2FBT is shown as a formula I-1:
the structural formula of the polymer PTP-2F4T-TP-BTZ is shown as the formula I-2:
the structural formula of the polymer PTP-2FBT-TP-2TBTZ is shown as a formula I-2:
wherein R is as defined for R in formula I.
The invention also provides a preparation method of the polymer, which comprises the following steps:
in the presence of a catalyst II and a ligand, 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 is subjected to one-step or multi-step reaction with a methyltin reagent of Ar1 or a borate compound, and then is subjected to polymerization reaction with a dimethyltin reagent of Ar2 to obtain the compound;
in formula 6, R is as defined in formula I;
the methyl tin reagent or borate compound of Ar1 or the bis-methyl tin reagent of Ar2 is selected from any one of the following compounds:
in the preparation method, the catalyst II is at least one of tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride and tris (dibenzylideneacetone) dipalladium;
the ligand is at least one of triphenylphosphine, tri (o-tolyl) phosphine and triphenylarsenic;
the molar ratio of the 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in the formula 6 to the methyltin reagent or borate compound of Ar1 is 2: 0.9 to 1.1;
the molar ratio of the methyltin reagent or borate compound of Ar1 to the catalyst i was 1: 0.01 to 0.20;
the molar ratio of the reaction product of the 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in the formula 6 and the methyl tin reagent of Ar1 or the borate compound to the catalyst II is 1: 0.01 to 0.10;
the molar ratio of the reaction product of the 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in the formula 6 and the methyl tin reagent of Ar1 or the borate compound to the ligand is 1: 0.08 to 0.80;
the temperature of the polymerization reaction is 90-140 ℃, and the time is 2-80 hours;
the polymerization reaction is carried out in the following solvents: at least one of toluene, chlorobenzene, and xylene.
Specifically, 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 is firstly reacted with a methyltin reagent shown in a formula 7, and a reaction product (namely, the formula 1) is subjected to a polymerization reaction with a dimethyltin reagent shown in a formula 13 to obtain a polymer shown in a formula I-1;
specifically, 4, 7-dibromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridine shown in formula 6 is reacted with (2-tri-n-butyltin) -thiophene shown in formula 8 to obtain a compound shown in formula 9, 7-bromo-2- (5-decylpentadecyl) -4- (thiophene-2-yl) - [1,2,3] triazolo [4,5-c ] pyridine shown in formula 9 is reacted with 4, 7-diboronate-benzo [ c ] [1,2,5] thiadiazole shown in formula 10 to obtain a compound shown in formula 11, 4, 7-bis (2- (5-decylpentadecyl) -4- (thiophene-2-yl) - [1 shown in formula 11, 2,3] triazolo [4,5-c ] pyridine-7-yl) benzo [ c ] [1,2,5] thiadiazole and N-bromosuccinimide shown as a formula 12 are reacted to obtain a compound shown as a formula 2, and the compound shown as the formula 2 and a methyltin reagent shown as a formula 13 are subjected to a polymerization reaction to obtain a polymer shown as a formula I-2;
specifically, 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in formula 6 and a methyl tin reagent shown in formula 13 are firstly reacted, and a reaction product (namely, formula 3) and the methyl tin reagent shown in formula 7 are subjected to polymerization reaction to obtain the polymer shown in formula I-3.
The preparation method also comprises the following purification steps:
after the polymerization reaction is finished, cooling the obtained reaction system, adding methanol, stirring and filtering at room temperature, sequentially extracting the obtained precipitate with methanol, acetone and normal hexane by using a Soxhlet extractor until the precipitate is colorless, removing micromolecules and a catalyst, and extracting with trichloromethane to obtain the product; or extracting the obtained precipitate with methanol, acetone, n-hexane, and chloroform in sequence with Soxhlet extractor, removing small molecules and catalyst, extracting with chlorobenzene to remove a little blue, and extracting with o-dichlorobenzene.
The triazole pyridine polymer shown in the formula I can be used as a semiconductor material layer and used for preparing an organic field effect transistor.
The invention has the following beneficial technical effects:
1. the raw materials are commercial products, the synthetic route is simple, the yield is high, and the method can be popularized to the synthesis of various linear chain or branched chain triazole pyridine polymers;
2. the triazole pyridine polymer has good symmetry and planarity, and can be used for preparing a field effect transistor;
3. the organic field effect transistor prepared by taking the triazole pyridine polymer as the semiconductor layer has higher hole mobility (mu) (the maximum is 9 multiplied by 10)─3cm2V-1s-1) And has good application prospect in organic field effect transistors.
Drawings
FIG. 1 is a scheme diagram of a triazole pyridine polymer shown in the formula I, wherein, FIG. 1(a) is a scheme diagram of a polymer PTP-2TBTZ-TP-2FBT shown in the formula I-1; FIG. 1(b) is a scheme showing the preparation of the polymer PTP-2F4T-TP-BT shown in I-2; FIG. 1(c) is a scheme for preparing the polymer PTP-2FBT-TP-2TBTZ shown in I-3.
FIG. 2 is a diagram of an ultraviolet-visible absorption spectrum of a triazole pyridine polymer shown in formula I, wherein FIG. 2(a) is a diagram of an ultraviolet-visible absorption spectrum of a polymer PTP-2TBTZ-TP-2FBT shown in I-1; FIG. 2(b) is a graph showing the UV-VIS absorption spectrum of the polymer PTP-2F4T-TP-BT shown in I-2; FIG. 2(c) is a graph showing the UV-VIS absorption spectrum of the polymer PTP-2FBT-TP-2TBTZ shown in I-3.
FIG. 3 is a cyclic voltammogram of the triazole pyridine polymer shown in formula I, wherein FIG. 3(a) is a cyclic voltammogram of the polymer PTP-2TBTZ-TP-2FBT shown in I-1; FIG. 3(b) is a cyclic voltammogram of PTP-2F4T-TP-BTZ polymer shown in I-2; FIG. 3(c) is a cyclic voltammogram of the polymer PTP-2FBT-TP-2TBTZ shown in I-3.
Fig. 4 is a schematic structural view of an organic field effect transistor.
FIG. 5 is a graph showing the output and transfer characteristics of the triazole pyridine polymer of the present invention, wherein FIG. 5(a) is a graph showing the output characteristics (left) and transfer characteristics (right) of a polymer field effect transistor in which the PTP-2TBTZ-TP-2FBT polymer of the formula I-1 is a semiconductor layer; FIG. 5(b) is a graph (left side) of the output characteristics and a graph (right side) of the transfer characteristics of a polymer field effect transistor in which the polymer PTP-2F4T-TP-BTZ shown in the formula I-2 is a semiconductor layer; FIG. 5(c) is a graph showing the output characteristics (left diagram) and the transfer characteristics (right diagram) of the polymer PTP-2FBT-TP-2TBTZ of the formula I-3, which is a semiconductor layer, of a polymer field effect transistor.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The invention provides a triazole pyridine receptor with a positioning effect, which is shown as a formula 1, a formula 2 or a formula 3:
in the formula 1, R is a straight chain or branched chain alkane with the total number of carbon atoms of 1-60, and can be 5-decyl pentadecyl;
in the formula 2, R is a straight chain or branched chain alkane with the total number of carbon atoms of 1-60, and can be 5-decyl pentadecyl;
in the formula 3, R is a linear or branched alkyl group having 1 to 60 carbon atoms in total, and specifically may be a 5-decylpentadecyl group.
The structural general formula of the triazole pyridine polymer provided by the invention is shown as formula I:
in the formula I, R is a straight chain or branched chain alkyl group with the total number of carbon atoms of 1-60, and n is a natural number between 5-100;
ar1 is the following group:
ar2 is the following group:
the application of the triazole pyridine polymer shown in the formula I which can be used as a semiconductor material layer and used for preparing an organic field effect transistor also belongs to the protection scope of the invention.
The organic field effect transistor prepared by taking the triazole pyridine polymer as the semiconductor layer has higher hole mobility (mu) (the maximum is 9 multiplied by 10)─3cm2V-1s-1) And has good application prospect in organic field effect transistors.
Example 1 Polymer PTP-2TBTZ-TP-2FBT, R is 5-decylpentadecyl (formula I-1)
The reaction equation is shown in FIG. 1 (a).
Firstly, preparation of compound shown in formula 1
(1)4, 7-dibromo-2H- [1,2,3] triazolo [4,5-c ] pyridine
2, 5-dibromo-3, 4-diaminopyridine (4.00g, 14.99mmol) and 60mL of acetic acid were added to a 100mL two-necked flask, sonicated for 10min, and then, while stirring, sodium nitrite (1.55g,22.48mmol) dissolved in 24mL of distilled water was dropped into the two-necked flask, and reacted at 30 ℃ for 24 hours. The product was washed twice with distilled water, then the product was filtered and transferred to a 250mL round bottom flask, added about 100mL ethanol and spin dried (with ethanol carrying water) and dried to give 4.05g of a white solid. Yield: 97.12 percent.
The structural characterization data is as follows:
mass spectrum: ESI-MS: [ M]-calcd for C5HBr2N4 -:276.85,found:276.90.
Nuclear magnetic hydrogen and carbon spectra:1H NMR(400MHz,DMSO)δ8.49(m,1H).13C NMR(100MHz,DMSO)δ144.65,140.37,132.44,131.32,103.92.
(2)4, 7-dibromo-2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-c ] pyridine (TP)
A100 mL two-necked flask was charged with 4, 7-dibromo-2H- [1,2,3] triazolo [4,5-c ] pyridine (2.00g,7.20mmol), potassium carbonate (1.99g, 14.40mmol), and 60mL of a N, N-dimethylformamide solution, and then purged with argon. Stirring was carried out at 90 ℃ for 1h, 5-decylpentadecyl iodide (4.13g, 8.64mmol) was added dropwise, and refluxing was carried out at 90 ℃ for 24 h. Extracted with water and dichloromethane and dried over anhydrous sodium sulfate. The solution was spun dry and then passed through a column (eluent petroleum ether: dichloromethane: 3:1) to obtain 3.78g of a liquid. Yield: 83.60 percent.
The structural characterization data is as follows:
mass spectrum: HR-MALDI-TOF: [ M + H ]]+calcd for C30H53Br2N4:629.26165,found:629.26092。
Nuclear magnetic hydrogen and carbon spectra:1H NMR(400MHz,CDCl3)δ8.34(s,1H),4.82(t,J＝8.0Hz,2H),2.15(m,J＝8.0Hz,2H),1.25–1.20(m,41H),0.88(t,J＝8.0Hz,6H).13C NMR(100MHz,CDCl3)δ146.44,143.25,141.70,132.71,108.09,58.04,37.19,33.52,32.93,31.91,30.47,30.09,29.68,29.64,29.34,26.63,23.61,22.67,14.09.
(3)4, 7-bis (5- (7-bromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridin-4-yl) thiophen-2-yl) benzo [ c ] [1,2,5] thiadiazole (formula 1, R is 5-decylpentadecyl)
A100 mL two-necked flask was charged with 4, 7-dibromo-2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-C ] pyridine (1.5g,2.39mmol), 4, 7-bis (5- (trimethylalkyl) thiophen-2-yl) benzo [ C ] [1,2,5] thiadiazole (0.75g, 1.20mmol), the catalyst bis (triphenylphosphine) palladium dichloride (0.043g, 0.06mmol), and chlorobenzene (60mL), purged with argon, and the reaction mixture was heated to 120 ℃ for 24H. Extracted with aqueous potassium fluoride solution and dichloromethane, and dried over anhydrous sodium sulfate. The solution was spun dry and then passed through a column (eluent ethyl acetate: dichloromethane: 1: 60) to give 1.03g of a red solid. Yield: 88.03 percent.
The structural characterization data is as follows:
mass spectrum: HR-MALDI-TOF: [ M + H ]]+calcd for C74H111Br2N10S3:1395.65016,found:1395.64808。
Nuclear magnetic hydrogen and carbon spectra:1H NMR(400MHz,CDCl3)δ8.52(d,2H),8.34(s,2H),8.25(d,2H),8.01(d,2H),4.87(t,J＝8.0Hz,4H),2.24(m,J＝8.0Hz,4H),1.41–1.24(m,82H),0.87(t,J＝8.0Hz,12H).13C NMR(100MHz,CDCl3)δ155.48,148.34,146.67,145.67,144.32,139.45,133.34,131.95,128.56,122.57,119.45,57.67,37.22,33.34,33.67,31.98,30.68,30.14,29.74,29.68,29.39,26.74,23.84,22.78,14.14.
preparation of polymer PTP-2TBTZ-TP-2FBT
4, 7-bis (5- (7-bromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridin-4-yl) thiophen-2-yl) benzo [ c ] [1,2,5] thiadiazole of formula 1 (100.0mg,0.072mmol) was charged to a reaction flask with 3,3' -difluoro-5, 5' -bis (trimethyltin) -2,2' -bithiophene of formula 13 (38.01mg,0.072mmol), the catalyst tris (dibenzylideneacetone) dipalladium (1.97mg, 0.0021mmol), the ligand tris (o-tolyl) phosphine (5.23mg, 0.017mmol), and chlorobenzene (5mL), three freeze-pump-thaw cycles were performed under argon to remove oxygen, and the reaction mixture was then heated to 120 ℃ for polymerization for 24 h. After cooling, 100mL of methanol was added, stirred at room temperature for 3h, and filtered. The obtained precipitate is loaded into a Soxhlet extractor for extraction. Firstly, methanol, acetone and normal hexane are used for extraction until the mixture is colorless, micromolecules and catalysts are removed, and then chloroform is used for extraction to obtain a final product of 96mg, wherein the yield is 94.55%.
The structural characterization data is as follows:
molecular weight: GPC Mn＝25.35kDa,PDI＝2.33。
Elemental analysis: calcd for C82H112F2N10S5：C 68.58,H 7.86,N 9.75,found:C 68.22,H 7.87,N 9.51。
As can be seen from the above, the compound has a correct structure and is a compound PTP-2TBTZ-TP-2FBT (R is 5-decylpentadecyl) shown in formula I-1, and the structural formula is shown as follows:
example 2 Polymer PTP-2F4T-TP-BTZ, R is 5-decylpentadecyl (formula I-2)
The reaction equation is shown in FIG. 1 (b).
Firstly, preparation of compound shown in formula 2
(4) The same step (1);
(5) the same step (2);
(6) 7-bromo-2- (5-decylpentadecyl) -4- (thiophen-2-yl) -2H- [1,2,3] triazolo [4,5-c ] pyridine
A100 mL two-necked flask was charged with 4, 7-dibromo-2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-c ] pyridine (1.5g,2.39mmol), 5-tributyltin-2-thiophene (0.89g, 2.39mmol), bis (triphenylphosphine) palladium dichloride (0.085g, 0.12mmol) as a catalyst, and chlorobenzene (60mL), purged with argon, and the reaction mixture was heated to 120 ℃ for 24H. Extracted with aqueous potassium fluoride solution and dichloromethane, and dried over anhydrous sodium sulfate. The solution was spin dried and then passed through a column (eluent petroleum ether: dichloromethane: 3:1) to give 1.21g of a yellow solid. Yield: 80.40 percent.
The structural characterization data is as follows:
mass spectrum: HR-MALDI-TOF: [ M + H ]]+calcd for C34H56BrN4S:631.34091,found:631.34416.
Nuclear magnetic hydrogen and carbon spectra:1H NMR(300MHz,CDCl3,δ):8.635(d,J＝3.0Hz,1H),8.51(s,1H),8.245(d,J＝3.0Hz,1H),8.01(s,1H),4.89(t,J＝6.0Hz,2H),2.22(m,J＝6.0Hz,2H),1.62-1.23(m,41H),0.86(t,J＝6.0Hz,6H).13C NMR(75MHz,CDCl3,δ):146.06,144.70,142.29,139.94,137.30,129.87,128.86,127.57,104.05,56.57,36.21,32.52,31.96,30.91,29.47,29.08,28.68,28.63,28.34,25.63,22.64,21.68,13.10.
(7)4, 7-bis (2- (5-decylpentadecyl) -4- (thien-2-yl) -2H- [1,2,3] triazolo [4,5-c ] pyridin-7-yl) benzo [ c ] [1,2,5] triazole
7-bromo-2- (5-decylpentadecyl) -4- (thien-2-yl) -2H- [1,2,3] triazolo [4,5-c ] pyridine (1.0g,1.59mmol),4, 7-bis (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzo [1,2,5] thiadiazole (0.28g,0.72mmol), the catalyst tris (dibenzylideneacetone) dipalladium (0.065g, 0.075mmol), the ligand tris (o-tolyl) phosphine (5.23mg, 0.017mmol), potassium carbonate (4mL,2M), aliquat 336(4 drops) and toluene (30mL) were charged to a reaction flask, protected with argon, and the reaction mixture was heated to 110 ℃ for 24H. Extracted with aqueous potassium fluoride solution and dichloromethane, and dried over anhydrous sodium sulfate. The solution was spun dry and then passed through a column (eluent ethyl acetate: dichloromethane: 1: 50) to give 0.66g of a red solid. Yield: 74.09%.
The structural characterization data is as follows:
mass spectrum: HR-MALDI-TOF: [ M + H ]]+calcd for C74H113N10S3:1237.83118,found:1237.83207。
Nuclear magnetic hydrogen and carbon spectra:1H NMR(400MHz,CDCl3)δ9.60(s,2H),8.75(s,2H),8.70(s,2H),7.635(d,J＝4.0Hz,2H),7.28(t,J＝8.0Hz,2H),4.91(t,J＝8.0Hz,4H),2.22(m,J＝8.0Hz,4H),1.29–1.22(m,82H),0.86(t,J＝8.0Hz,12H).13C NMR(100MHz,CDCl3)δ153.84,146.29,146.16,143.93,141.95,138.53,130.87,129.84,128.58,127.43,119.83,57.37,37.33,33.60,33.13,31.92,30.59,30.12,29.70,29.65,29.36,26.70,23.80,22.68,14.11.
(8)4, 7-bis (4- (5-bromothien-2-yl) -2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-c ] pyridin-7-yl) benzo [ c ] [1,2,5] triazole (formula 2)
4, 7-bis (2- (5-decylpentadecyl) -4- (thien-2-yl) -2H- [1,2,3] triazolo [4,5-c ] pyridin-7-yl) benzo [ c ] [1,2,5] triazole (0.50g,0.41mmol) was added to 40ml of chloroform solution, followed by ice-water bath, N-dimethylformamide (0.16g,0.89mmol) was added at about 0 deg.C, and the reaction mixture was reacted at room temperature for 24H. Extracted with dichloromethane and dried over anhydrous sodium sulfate. The solution was spin dried and then passed through a column (eluent petroleum ether: dichloromethane: 3:1) to give 0.41g of a red solid. Yield: 72.57 percent.
The structural characterization data is as follows:
mass spectrum: HR-MALDI-TOF: [ M + H ]]+calcd for C74H111Br2N10S3:1395.65016,found:1395.64808。
Nuclear magnetic hydrogen and carbon spectra:1H NMR(300MHz,CDCl3)δ9.60(s,2H),8.73(s,2H),8.46(s,2H),7.235(d,J＝6.0Hz,2H),4.91(t,J＝6.0Hz,4H),2.22(m,J＝6.0Hz,4H),1.55-1.21(m,82H),0.86(t,J＝6.0Hz,12H).13C NMR(100MHz,CDCl3)δ153.68,146.11,144.98,143.88,143.39,138.12,131.59,130.96,127.15,119.93,118.16,57.40,37.35,33.62,33.15,31.93,30.57,30.14,29.72,29.66,29.37,26.71,23.82,22.69,14.11.
secondly, preparation of polymer PTP-2F4T-TP-BTZ
4, 7-bis (4- (5-bromothien-2-yl) -2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-c ] pyridin-7-yl) benzo [ c ] [1,2,5] triazole of formula 2 (100.0mg,0.072mmol) with 3,3' -difluoro-5, 5' -bis (trimethyltin) -2,2' -bithiophene of formula 13 (38.01mg,0.072mmol), the catalyst tris (dibenzylideneacetone) dipalladium (1.97mg, 0.0021mmol), the ligand tris (o-tolyl) phosphine (5.23mg, 0.017mmol), and toluene (5mL) were added to a reaction flask, three freeze-pump-thaw cycles were performed under argon to remove oxygen, and the reaction mixture was then heated to 120 ℃ for polymerization for 25 min. After cooling, 100mL of methanol was added, stirred at room temperature for 3h, and filtered. The obtained precipitate is loaded into a Soxhlet extractor for extraction. Firstly, methanol, acetone, normal hexane and trichloromethane are used for extraction, after the extraction is carried out until the product is colorless, micromolecules and catalysts are removed, chlorobenzene extraction is carried out until a very small amount of blue is extracted, and then ortho-dichlorobenzene is used for extraction to obtain a final product of 66mg, wherein the yield is 64.75%.
The structural characterization data is as follows:
molecular weight: GPC Mn＝48.64kDa,PDI＝1.47。
Elemental analysis: calcd for C82H112F2N10S5：C 68.58,H 7.86,N 9.75,found:C 68.17,H 7.88,N 9.46。
As can be seen from the above, the compound has a correct structure and is a compound PTP-2F4T-TP-BTZ shown in the formula I-2, the structural formula is shown as follows, and R is 5-decylpentadecyl;
example 3 Polymer PTP-2FBT-TP-2TBTZ, R is 5-decylpentadecyl (formula I-3)
The reaction equation is shown in FIG. 1 (c).
Firstly, preparation of compound shown in formula 3
(9) The same step (1);
(10) the same step (2);
(11)4,4'- (3,3' -difluoro- [2,2 '-dithiophene ] -5,5' -diyl) bis (7-bromo-2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-c ] pyridine) (formula 3)
A100 mL two-necked flask was charged with 4, 7-dibromo-2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-c ] pyridine (1.5g,2.39mmol), 3,3' -difluoro-5, 5' -bis (trimethylalkyltin) -2,2' -bithiophene (0.63g, 1.20mmol), the catalyst bis (triphenylphosphine) palladium dichloride (0.043g, 0.06mmol) and chlorobenzene (60mL), purged with argon, and the reaction mixture was heated to 120 ℃ for 24H. Extracted with aqueous potassium fluoride solution and dichloromethane, and dried over anhydrous sodium sulfate. The solution was spin dried and then passed through a column (eluent petroleum ether: dichloromethane: 4: 1) to give 1.26g of a red solid. Yield: 81.55 percent.
The structural characterization data is as follows:
mass spectrum: HR-MALDI-TOF: [ M + H ]]+calcd for C68H107Br2F2N8S2:297.63745,found:1297.63610。
Nuclear magnetic hydrogen and carbon spectra:1H NMR(400MHz,CDCl3)δ8.49(s,2H),8.31(s,2H),4.87(t,J＝8.0Hz,4H),2.19(m,J＝8.0Hz,4H),1.40–1.24(m,82H),0.87(t,J＝8.0Hz,12H).13CNMR(100MHz,CDCl3)δ155.99,153.34,147.10,144.02,143.23,138.12,137.29,120.21,119.95,116.35,116.27,106.16,57.75,37.30,33.59,33.04,31.95,30.52,30.14,29.73,29.68,29.38,26.70,23.72,22.70,14.11.
secondly, preparation of polymer PTP-2FBT-TP-2TBTZ
4,4'- (3,3' -difluoro- [2,2 '-dithiophene ] -5,5' -diyl) bis (7-bromo-2- (5-decylpentadecyl) -2H- [1,2,3] triazolo [4,5-c ] pyridine) (100.0mg,0.077mmol) represented by formula 3 and 4, 7-bis (5- (trimethylstannyl) thiophen-2-yl) benzo [ c ] [1,2,5] thiadiazole (48.20mg,0.077mmol) represented by formula 7, tris (dibenzylideneacetone) dipalladium (2.12mg, 0.0023mmol) as a catalyst, tris (o-tolyl) phosphine (5.63mg, 0.019mmol) as a ligand and chlorobenzene (5mL) were added to a reaction flask, three freeze-pump-thaw cycles were performed under argon to remove oxygen, and the reaction mixture was then heated to 120 ℃ for polymerization for 24 h. After cooling, 100mL of methanol was added, stirred at room temperature for 3h, and filtered. The obtained precipitate is loaded into a Soxhlet extractor for extraction. Firstly, methanol, acetone and normal hexane are used for extraction until the mixture is colorless, micromolecules and catalysts are removed, and then chloroform is used for extraction to obtain a final product of 98mg, wherein the yield is 96.52%.
The structural characterization data is as follows:
molecular weight: GPC Mn＝27.68kDa,PDI＝2.39。
Elemental analysis: calcd for C82H112F2N10S5：C 68.58,H 7.86,N 9.75,found:C 68.35,H 7.79,N 9.65。
As can be seen from the above, the compound has a correct structure and is a compound PTP-2FBT-TP-2TBTZ shown in formula I-3, and the structural formula is shown as follows (R is 5-decylpentadecyl):
example 4 optical, electrochemical and field Effect transistor Performance of the polymers PTP-2TBTZ-TP-2FBT, PTP-2F4T-TP-BTZ, PTP-2FBT-TP-2TBTZ
(1) Optical and electrochemical properties of the polymers PTP-2TBTZ-TP-2FBT, PTP-2F4T-TP-BTZ and PTP-2FBT-TP-2TBTZ
FIG. 2 is a graph showing the UV-VIS absorption spectra of the polymers PTP-2TBTZ-TP-2FBT (FIG. 2(a)), PTP-2F4T-TP-BTZ (FIG. 2(b)), and PTP-2FBT-TP-2TBTZ (FIG. 2(c)) in solution and in film.
As can be seen from FIG. 2, the optical band gaps of the polymers PTP-2TBTZ-TP-2FBT, PTP-2F4T-TP-BTZ and PTP-2FBT-TP-2TBTZ are 1.61eV, 1.79eV and 1.63eV, respectively (the optical band gaps are according to equation E)g1240/λ calculation, where EgIs the optical band gap, and λ is the boundary value of the ultraviolet absorption curve). As can be seen from FIG. 2, all three polymers wereHas stronger intramolecular charge transfer peak, which indicates that the intermolecular acting force of the polymer is stronger.
FIG. 3 is a cyclic voltammogram of the films of the polymers PTP-2TBTZ-TP-2FBT (FIG. 2(a)), PTP-2F4T-TP-BTZ (FIG. 2(b)), and PTP-2FBT-TP-2TBTZ (FIG. 2 (c)). The measurements were performed at the electrochemical workstation CHI660c and tested using a conventional three-electrode configuration with platinum as the working electrode, platinum wire as the counter electrode, silver/silver chloride as the reference electrode, and tetrabutylammonium hexafluorophosphate as the supporting electrolyte. The test was performed in acetonitrile solution. The cyclic voltammetry conditions were: the scan range is-1.6 to 1.6 volts (vs. Ag/AgCl) and the scan rate is 50 millivolts per second. Both polymers have oxidation peaks and reduction peaks and can be used as organic semiconductor materials. According to the cyclic voltammetry curve, the HOMO energy levels of the polymers PTP-2TBTZ-TP-2FBT, PTP-2F4T-TP-BTZ and PTP-2FBT-TP-2TBTZ are respectively-5.52 eV, -5.54 eV and-5.42 eV, and the LUMO energy levels are respectively-3.91 eV, -3.75 eV and-3.79 eV.
(2) Performance of field effect transistors of the polymers PTP-2TBTZ-TP-2FBT, PTP-2F4T-TP-BTZ and PTP-2FBT-TP-2TBTZ
FIG. 4 is a schematic structural diagram of an organic field effect transistor, which adopts a glass substrate, and is ultrasonically cleaned in secondary water, ethanol and acetone and dried by nitrogen. To be provided with
5nm titanium and 30nm gold are vacuum evaporated at the speed of (1) to form a source/drain electrode. The polymer obtained in example 2 was a semiconductor layer, and an active layer was formed on a glass substrate by eccentric spin coating in an o-dichlorobenzene solution having a concentration of 10mg/ml to a thickness of 25nm and annealed on a 150 ℃ hot stage for 10 minutes.
Then, polymethyl methacrylate with the thickness of 900 nanometers is formed on the surfaces of the polymer films obtained in the examples 1,2 and 3 by spin coating to be used as a field effect tube insulating layer, and the solvent is removed for 60 minutes at 90 ℃; and thermally evaporating 110nm thick aluminum on the insulating layer through a mask plate to be used as a gate electrode, and finishing the preparation of the field effect transistor.
The electrical properties of the field effect devices prepared were measured at room temperature with a Keithley 4200SCS semiconductor tester. Determining the Properties of OFETsTwo key parameters of energy are: carrier mobility (μ) and on-off ratio (I) of the deviceon/Ioff). The mobility refers to the average drift velocity of a carrier (unit is cm) under the action of a unit electric field2 V-1s-1) Which reflects the mobility of holes or electrons in a semiconductor under an electric field. The on-off ratio is defined as: the ratio of the current in the "on" state and the "off" state of the transistor reflects the performance of the device switch. For a high performance field effect transistor, the mobility and switching ratio should be as high as possible.
FIG. 5 is a graph of the output and transfer characteristics of field effect transistors made with the polymers PTP-2TBTZ-TP-2FBT, PTP-2F4T-TP-BTZ, and PTP-2FBT-TP-2 TBTZ. All the polymer field effect transistors show obvious hole transmission characteristics, which indicates that the polymer is a P-type material.
The carrier mobility can be calculated from the equation:
IDS＝(W/2L)Ciμ(VG–VT)2(saturation region)
Wherein, IDSIs the drain current, μ is the carrier mobility, VGIs the gate voltage, VTIs the threshold voltage, W is the channel width, L is the channel length, CiIs an insulator capacitor. Utilizing (I)DS，sat)1/2To VGPlotting, and performing linear regression to obtain carrier mobility (μ) from the slope of the regression line, and determining V from the intercept of the regression line and the X-axisT。
The mobility can be calculated from the slope of the transfer curve according to the formula, and the device properties of the polymer field effect transistor prepared in each of the above examples are shown in table 1. The on-off ratio of the three polymers can be derived from the ratio of the maximum to minimum of the source-drain current.
The experimental result shows that the polymer is an excellent novel high-mobility material.
TABLE 1 device Performance of the Polymer field Effect transistor
Claims (9)
1. A compound represented by formula 1, formula 2 or formula 3:
wherein R is a straight chain or branched alkyl group having 1 to 60 carbon atoms in total.
2. A process for the preparation of a compound according to claim 1, comprising the steps of:
s1, reacting 2, 5-dibromo-3, 4-diaminopyridine shown in a formula 4 with sodium nitrite in an aqueous solution of acetic acid to obtain 4, 7-dibromo-2-hydrogen- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 5;
s2, in the presence of potassium carbonate, reacting 4, 7-dibromo-2-hydrogen- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 5 with iodoalkane to obtain 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6;
the chemical formula of the alkyl iodide is R-I, and R is a straight chain or branched chain alkyl group with the total number of carbon atoms of 1-60;
s3, in the presence of a catalyst I, carrying out one-step or multi-step coupling reaction on 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 and a methyl tin reagent of Ar1 or a borate compound to obtain a compound shown in a formula 1, a formula 2 or a formula 3 of claim 1;
the methyltin reagent or borate compound of Ar1 is selected from any one of the following compounds:
3. the method of claim 2, wherein: in step S1, in the aqueous solution of acetic acid, the volume ratio of water to acetic acid is 1: 0.5 to 5.0;
the molar ratio of the 2, 5-dibromo-3, 4-diaminopyridine shown in formula 4 to the sodium nitrite is 1: 0.5 to 4.0;
the reaction temperature is 10-40 ℃, and the reaction time is 2-60 hours;
in step S2, the molar ratio of 4, 7-dibromo-2-hydro- [1,2,3] triazolo [4,5-c ] pyridine represented by formula 5, the alkyl iodide and the potassium carbonate is 1: 1.0-2.0: 1.0 to 4.0;
the reaction temperature is 80-120 ℃, and the reaction time is 2-48 hours;
the reaction is carried out in N, N-dimethylformamide;
in step S3, the molar ratio of 4, 7-dibromo-2- (5-decylpentadecyl) - [1,2,3] triazolo [4,5-c ] pyridine represented by formula 6 to the methyltin reagent or borate compound of Ar1 is 2: 0.9 to 1.1;
the molar ratio of the methyltin reagent or borate compound of Ar1 to the catalyst i was 1: 0.01 to 0.20;
the reaction temperature is 80-130 ℃, and the reaction time is 2-80 hours;
the reaction is carried out in the following solvents: at least one of toluene, chlorobenzene, and xylene;
the catalyst I is at least one of tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride and tris (dibenzylideneacetone) dipalladium.
4. Triazole pyridine polymer shown as formula I:
in the formula I, R is a straight chain or branched chain alkyl group with the total number of carbon atoms of 1-60, and n is a natural number between 5-100;
ar1 is the following group:
ar2 is the following group:
5. The polymer of claim 4, wherein: the polymer is a polymer PTP-2TBTZ-TP-2FBT, a polymer PTP-2F4T-TP-BTZ or a polymer PTP-2FBT-TP-2 TBTZ;
the structural formula of the polymer PTP-2TBTZ-TP-2FBT is shown as a formula I-1:
the structural formula of the polymer PTP-2F4T-TP-BTZ is shown as a formula I-2:
the structural formula of the polymer PTP-2FBT-TP-2TBTZ is shown as a formula I-3:
wherein R is as defined in formula I.
6. A process for the preparation of a polymer as claimed in claim 4 or 5, comprising the steps of:
in the presence of a catalyst II and a ligand, 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in a formula 6 is subjected to one-step or multi-step reaction with a methyltin reagent of Ar1 or a borate compound, and then is subjected to polymerization reaction with a dimethyltin reagent of Ar2 to obtain the compound;
in formula 6, R is as defined in formula I;
the methyl tin reagent or borate compound of Ar1 or the bis-methyl tin reagent of Ar2 is selected from any one of the following compounds:
7. the method of claim 6, wherein: the catalyst II is at least one of tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride and tris (dibenzylideneacetone) dipalladium;
the ligand is at least one of triphenylphosphine, tri (o-tolyl) phosphine and triphenylarsenic;
the molar ratio of the 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in the formula 6 to the methyltin reagent or borate compound of Ar1 is 2: 0.9 to 1.1;
the molar ratio of the methyltin reagent or borate compound of Ar1 to the catalyst i was 1: 0.01 to 0.20;
the molar ratio of the reaction product of the 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in the formula 6 and the methyl tin reagent of Ar1 or the borate compound to the catalyst II is 1: 0.01 to 0.10;
the molar ratio of the reaction product of the 4, 7-dibromo-2-alkyl- [1,2,3] triazolo [4,5-c ] pyridine shown in the formula 6 and the methyl tin reagent of Ar1 or the borate compound to the ligand is 1: 0.08 to 0.80;
the temperature of the polymerization reaction is 90-140 ℃, and the time is 2-80 hours;
the polymerization reaction is carried out in the following solvents: at least one of toluene, chlorobenzene, and xylene.
8. Use of a polymer according to claim 4 or 5 as a layer of semiconducting material in the manufacture of an organic field effect transistor.
9. An organic field effect transistor whose semiconductor material layer is made of the polymer of claim 4 or 5.
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