CN112745485B - 一种含锇共轭聚合物及其制备方法与应用 - Google Patents
一种含锇共轭聚合物及其制备方法与应用 Download PDFInfo
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- CN112745485B CN112745485B CN202010057042.4A CN202010057042A CN112745485B CN 112745485 B CN112745485 B CN 112745485B CN 202010057042 A CN202010057042 A CN 202010057042A CN 112745485 B CN112745485 B CN 112745485B
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- osmium
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- conjugated polymer
- containing conjugated
- carbon atoms
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- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 229910052762 osmium Inorganic materials 0.000 title claims abstract description 93
- 229920000547 conjugated polymer Polymers 0.000 title claims abstract description 84
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
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- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
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- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 36
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- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 9
- 238000012512 characterization method Methods 0.000 description 9
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 9
- 238000012790 confirmation Methods 0.000 description 9
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- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 9
- 238000003760 magnetic stirring Methods 0.000 description 9
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- 229910000073 phosphorus hydride Inorganic materials 0.000 description 9
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- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 8
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical group CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 5
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Abstract
Description
技术领域
本发明属于金属有机化学技术领域,具体涉及一种含锇共轭聚合物及其制备方法与应用。
背景技术
共轭聚合物(Conjugated polymer)是指一类具有大共轭离域π键的聚合物。其主要特征是电子和能量可以在整个高分子主链上迁移。不仅拥有优异的光电性能,还具备了良好的加工性能和力学性能(Chemical reviews 2007,107(4),1324-38.)。因其在发光二极管(J.Mater.Chem.C 2015,3(13),2974-3002)、太阳能电池(Advanced materials 2014,26(7),1006-24.)、化学传感器(Nature communications 2014,5,5404.)等领域的应用而备受关注。然而传统有机共轭聚合物材料已经不能满足未来能源化学的发展需要。
有机基元骨架中引入过渡金属能够带来物质基本属性的颠覆性突变,从而展现出独特的性能。例如在2013年,Xia等(Nat.Chem.2013,5,698-703)报道了一种新型的金属桥位金属杂稠环化合物——锇杂戊搭炔化合物,该化合物具有聚集诱导发光增强效应、大Stock位移、发光寿命长等特点,在有机光电领域具有重要的应用前景。2014年,Xia等报道了一类特定取代基的锇杂戊搭炔化合物,该类化合物具有很好的紫外-可见光吸收性能(Angew.Chem.Int.Ed.2014,53,6232-6236)。2015年,Xia等又报道了另一类金属桥位的锇杂稠环化合物,其具有良好的光声成像和光热性能,在肿瘤的诊断和治疗中具有潜在的应用前景(Angew.Chem.Int.Ed.2015,54,6181-6185)。2017年,Xia等又报道了另一类含铆钉基团取代的金属锇杂戊搭炔衍生物,其具有良好的单分子电导值(J.Am.Chem.Soc.,2017,139,14344-14347)。
金属有机π共轭(dπ-pπ共轭)体系与纯有机π共轭(pπ-pπ共轭)体系性质有较大差别。含过渡金属的共轭高分子与传统的纯有机共轭高分子同样也有较大的差别。将过渡金属元素引入到共轭高分子的主链骨架中,能增强其自旋-轨道耦合(spin–orbit coupling,SOC)和促进单线态向三重态的系间窜越(intersystem crossing,ISC),以使共轭聚合物获得更多的三重激发态,从而展现不同的物理特性(Chem.Soc.Rev.2016,45(19),5264-5295.)。其金属中心与相邻的共轭有机单元相比,更具富电子结构特征。能够诱导电子和能量在高分子上更好得迁移。同时由于过渡金属种类多、价态可调控、激发态寿命较长、功能配体可设计性强,不仅增加聚合物结构的可设计性,不同功能导向的连接基团还可以实现最终聚合物的功能化。含过渡金属的共轭高分子有望成为一类全新功能材料,应用于能源化学领域。
然而此类聚合物的合成极度困难,进一步阻碍了其性能应用研究。因此,发展一种简便快捷地合成含过渡金属共轭聚合物的方法和策略就显得尤为重要。
发明内容
本发明的目的在于提供一种含锇共轭聚合物,该含锇共轭聚合物的重复单元由金属杂环锇杂戊搭炔基团、共轭连接基团R1和乙烯基团组成,上述重复单元中该金属杂环锇杂戊搭炔基团的3号位与该共轭连接基团R1连接,该共轭连接基团R1再与该乙烯基团连接,然后该乙烯基团与下一个金属杂环锇杂戊搭炔基团的7号位连接,其结构式如下:
含锇共轭聚合物
上述[Os]为OsAL2、OsA2L或OsL3,其中,A为-H、卤素、-SCN或-CN;L为膦配体、CO配体、吡啶类配体、氮杂环卡宾配体、腈类配体和异氰类双电子配体中的至少一种;其中,卤素为-F、-Cl、-Br或-I;
上述Y为CH2、O、C(COO(CH2)kMe)2、N或S,该分子式中k为0~18的整数,优选0~12的整数,更优选0~6的整数;
上述共轭连接基团R1为取代或未取代的芳基,取代或未取代的烯基,取代或未取代的炔基,其中,乙烯基团为反式乙烯基团;
上述Z-为阴离子。
在本发明的一个优选实施方案中,所述阴离子包括F-、Cl-、Br-、I-、BF4 -、H2PO4 -、C2O4 2-、SO4 2-、CF3SO3 -、CH3COO-、(CF3SO2)2N-、NO3 -、ClO4 -、PF6 -和BPh4 -;进一步,Z-为Cl-、Br-、BF4 -、CF3SO3 -、PF6 -或BPh4 -。
上述结构式中m为3~300的整数,优选3~200的整数,更优选3~100的整数。
具体地,所述[Os]中的L,其膦配体为3~24个碳原子,优选5~20个碳原子,更优选6~18个碳原子的烷基膦、环烷基膦或芳基膦,优选地,所述膦配体为三甲基膦、三乙基膦、三丙基膦、三异丙基膦、三叔丁基膦、三环己基膦或三苯基膦;
进一步,所述[Os]中的L,其吡啶类配体为含有吡啶或联吡啶结构单元的配体,优选地,所述吡啶类配体为甲基吡啶、乙基吡啶、1,4-联吡啶、1,2-二(4-吡啶基)乙烯、乙烯基吡啶、乙炔基吡啶、吡啶硼酸、氨基吡啶、氰基吡啶、巯基吡啶、二甲胺基吡啶、苯基吡啶或1,2-双(4-吡啶基)乙烷;
进一步,所述[Os]中的L,其氮杂环卡宾配体为任何含有氮杂环卡宾结构单元的配体,优选地,所述氮杂环卡宾配体为咪唑型氮杂环卡宾、咪唑啉型氮杂环卡宾、噻唑型氮杂环卡宾或***型氮杂环卡宾;
进一步,所述[Os]中的L,其腈类配体为含有腈基结构单元的配体,优选地,所述腈类配体为乙腈、丙腈或苯腈;
进一步,所述[Os]中的L,其异氰类双电子配体为含有异氰基结构单元的配体,优选地,所述异氰类双电子配体为环己基异氰、叔丁基异氰或苯基异氰。
在本发明的一个优选实施方案中,所述[Os]中的L为三苯基膦、三甲基膦、三乙基膦、三丙基膦、三异丙基膦、三叔丁基膦、三环己基膦、甲基吡啶、乙基吡啶、1,4-联吡啶、1,2-二(4-吡啶基)乙烯、乙烯基吡啶、乙炔基吡啶、吡啶硼酸、氨基吡啶、氰基吡啶、巯基吡啶、二甲胺基吡啶、苯基吡啶、1,2-双(4-吡啶基)乙烷、咪唑型氮杂环卡宾、咪唑啉型氮杂环卡宾、噻唑型氮杂环卡宾、***型氮杂环卡宾、乙腈、丙腈、苯腈、环己基异氰、叔丁基异氰和苯基异氰中的至少一种;
具体地,所述[Os]中的L2为选自双齿氮配体、双齿膦配体、双齿碳-氮配体或双齿氧-氮配体。
进一步,所述[Os]中的L2,其双齿氮配体是指以双齿氮原子作为配位原子的配体,该双齿氮配体包括乙二胺、2,2'-联吡啶和1,10-菲罗啉;
进一步,所述[Os]中的L2,其双齿膦配体是指以双齿磷原子作为配位原子的配体,该双齿膦配体包括DPPM(Bis-(diphenylphosphino)methane,1,1-双(二苯基膦)甲烷)、DPPE(1,2-Bis(diphenylphosphino)ethane,1,2-双(二苯基膦)乙烷、DPPP(1,3-Bis(diphenylphosphino)propane和1,3-双(二苯基膦)丙烷;
进一步,所述[Os]中的L2,其双齿碳-氮配体是指以双齿碳-氮原子作为配位原子的配体,该双齿碳-氮配体包括邻苯基吡啶;
进一步,所述[Os]中的L2,其双齿氧-氮配体是指以双齿氧-氮原子作为配位原子的配体,该双齿氧-氮配体包括8-羟基喹啉。
在本发明的一个优选实施方案中,所述[Os]中的L2为一个整体,且L2为乙二胺、2,2'-联吡啶、1,10-菲罗啉、1,1-双(二苯基膦)甲烷、1,2-双(二苯基膦)乙烷、1,3-双(二苯基膦)丙烷、邻苯基吡啶或8-羟基喹啉;
具体地,所述[Os]中的AL2为三联吡啶或三齿Pincer(钳形)配体,该三齿Pincer(钳形)配体包括钳形配体,该钳形配体包括PPP、PNP、PCP、NNN、NCN、NPN、ONO、OPO、OCO、SCS和CCC三齿配体。
在本发明的一个优选实施方案中,所述[Os]中的AL2为一个整体,且AL2为三联吡啶、PPP、PNP、PCP、NNN、NCN、NPN、ONO、OPO、OCO、SCS或CCC型三齿配体。
进一步优选地,所述芳基为苯基、双联苯基、三联苯基、萘基、蒽基、菲基、芘基、噻吩基、双联噻吩基、三联噻吩基、噻吩乙烯噻吩基、噻唑基、噻二唑基、并噻二唑基、并三噻吩基、呋喃基、吡啶基、吡咯基、卟啉基、芴基、双联芴基、三联芴基、咔唑基、双联咔唑基、三联咔唑基、苯并噻二唑基、四苯乙烯基、六苯并蔻基、吡咯并吡咯二酮基、苯并二噻吩基、引达省并二噻吩基、硅芴基、二噻吩并环芴二烯基、二噻吩并噻咯基、二噻吩并吡咯基、三苯胺基、吡咯并吡咯二酮基、萘并二噻二唑基、萘四羧酸二酰亚胺基、苝四羧酸二酰亚胺基、异靛蓝基、噻吩并吡咯二酮基、苯并吡咯二酮基、苯并***基、噻二唑并苯并***基、吡啶并噻二唑基或噻吩并[3,4-b]噻吩基;
进一步,该芳基能够提高所述含锇共轭聚合物的导电性能;该芳基的各个位置能够发生取代反应;
更进一步,与该芳基发生取代反应的取代基包括1~28个碳原子、优选1~20个碳原子、更优选1~14个碳原子的烷基,1~20个碳原子、优选1~17个碳原子、更优选1~14个碳原子的烷氧基、烷硫基、酰基、酯基、胺基、酰胺基,2~20个碳原子、优选2~17个碳原子、更优选2~8个碳原子取代的酰胺基,3~20个碳原子、优选3~17个碳原子、更优选3~8个碳原子的环烷基,1~20个碳原子、优选1~17个碳原子、更优选1~14个碳原子的烯基、炔基、硝基、氰基、卤素,上述取代基能够提高该含锇共轭聚合物的水溶性;
具体地,上述1~28个碳原子的烷基为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、仲戊基、叔戊基、正己基、异己基、新己基、仲己基、叔己基、正庚基、异庚基、新庚基、仲庚基、叔庚基、正辛基、异辛基、新辛基、仲辛基、叔辛基、正十二烷基、正十六烷基、正十八烷基、正二十烷基、 2-乙基己基、2-丁基己基、2-己基辛基、2-辛基癸基、2-癸基十二烷基、2-癸基十四烷基或2-十二烷基十六烷基。
具体地,上述1~20个碳原子的烷氧基为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、异戊氧基、新戊氧基、仲戊氧基、叔戊氧基、正己氧基、异己氧基、新己氧基、仲己氧基、叔己氧基、正庚氧基、异庚氧基、新庚氧基、仲庚氧基、叔庚氧基、正辛氧基、异辛氧基、新辛氧基、仲辛氧基、叔辛氧基、正十二烷氧基、正十六烷氧基、正十八烷氧基或正二十烷氧基。
具体地,上述1~20个碳原子的烷硫基为甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、异戊硫基、新戊硫基、仲戊硫基、叔戊硫基、正己硫基、异己硫基、新己硫基、仲己硫基、叔己硫基、正庚硫基、异庚硫基、新庚硫基、仲庚硫基、叔庚硫基、正辛硫基、异辛硫基、新辛硫基、仲辛硫基、叔辛硫基、正十二烷硫基、正十六烷硫基、正十八烷硫基或正二十烷硫基。
具体地,上述1~20个碳原子的胺基为甲胺基、乙胺基、丙胺基、丁胺基、戊胺基、己胺基、庚胺基、辛胺基、二甲胺基(NMe2)、二乙胺基(NEt2)、二丙胺基、二丁胺基、正十二胺基、正十六胺基、正十八胺基或正二十胺基。
具体地,上述取代的2~20个碳原子的酰胺基是指上述的酰胺基中的酰胺键上与N原子相连的H被1~20个碳原子、优选1~17个碳原子、更优选1~8个碳原子的烷基取代后形成的取代基。所述1~20个碳原子、优选1~17个碳原子、更优选1~8个碳原子的烷基与上述相同。
具体地,上述3~20个碳原子的环烷基为环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环十二烷基、环十六烷基、环十八烷基或环二十烷基。
具体地,上述能提高水溶性的取代基为聚乙二醇残基、透明质酸残基、聚丙烯酸或糖类衍生物残基。该聚乙二醇残基是指聚乙二醇的其中一个末端上的羟基去掉H后剩余的部分;该聚乙二醇的重均分子量为200~200000。该透明质酸残基是指透明质酸的D-葡萄糖醛酸或N-乙酰葡糖胺的任意一个羟基去掉H后剩余的部分,或透明质酸的D-葡萄糖醛酸的羧基去掉羟基(-OH)后剩余的部分;该透明质酸的重均分子量为2000-2000000。该糖类衍生物残基是指糖类衍生物的任意一个羟基去掉氢原子后剩余的部分;该糖类衍生物为葡萄糖、蔗糖、麦芽糖、半乳糖、乳糖、果糖或唾液酸的衍生物;该糖类衍生物为葡萄糖醛酸、葡萄糖缩醛、葡萄糖半缩醛或羧甲基乳糖。
与该烯基或炔基发生取代反应的取代基为2~80个碳原子、优选2~60个碳原子、更优选2~40个的取代或未取代的芳基,其中,该取代或未取代的芳基与上述相同。
在本发明的一个优选实施方案中,所述[Os]中的A为H、F、Cl、Br或SCN;[Os]中的L为CO配体、三苯基膦配体、三甲基膦配体和三乙基膦配体中的至少一种;上述共轭连接基团R1为 中的至少一种,上述n为0~30的整数,优选0~20的整数,更优选0~12的整数;上述X为氢、氟、氨基、硝基或1~32个碳原子,优选1~20个碳原子,更优选1~16个碳原子的烷氧基。
在本发明的一个优选实施方案中,含锇共轭聚合物为如下之一:
上述[Os]为OsCl(PPh3)2;n为0~30的整数,优选0~20的整数,更优选0~12的整数;m为3~300的整数,优选3~200的整数,更优选3~100的整数;X为氢、氟、氨基、硝基或1~32个碳原子,优选1~20个碳原子,更优选1~16个碳原子的烷氧基。
本发明的另一目的在于提供一种含锇共轭聚合物的制备方法,该技术方案包括步骤:将含锇共轭聚合物的单体溶于有机溶剂中,在酸性条件下进行聚合反应,即得该含锇共轭聚合物,其反应式如下:
在本发明的一个优选实施方案中,所述酸包括无机酸和有机酸。
进一步优选地,所述无机酸包括HClO4、HI、HBr、HCl、HNO3、H2SeO4、H2SO4、HClO3、H2C2O4、H2SO3、H3PO4、HNO2、HF、H2CO3、H2S、HClO、H3BO3和H2SiO3;
进一步优选地,所述有机酸包括CH3SO3H、CF3COOH、CCl3COOH、CHCl2COOH、CH3COOH和HCOOH。
在本发明的一个优选实施方案中,其反应温度为-100~200℃。
在本发明的一个优选实施方案中,其反应时间为1分钟~2天,优选0.5小时~1天。
在本发明的一个优选实施方案中,所述有机溶剂包括二氯甲烷、二氯乙烷、氯仿、甲醇、乙醇、丙酮、丁酮、四氢呋喃、二甲基亚砜、N,N-二甲基甲酰胺、甲苯、苯、二氧六环、***和乙腈,其中优选二氯甲烷。
上述聚合反应可被2~80个碳原子、优选2~60个碳原子、更优选2~40个碳原子的取代基取代的末端炔封端终止,该取代基包括取代或未取代的芳基、烷基和环烷基。
将获得的产物进行浓缩、沉淀后得到固体物质,再将该固体物质经过滤、洗涤分离后即得所述含锇共轭聚合物。
本发明的再一目的在于提供上述含锇共轭聚合物在有机光电器件中的应用,该有机光电器件具体包括在太阳能电池、发光二级管,场效应晶体管、化学传感器和化学开关等领域的应用。
优选地,该含锇共轭聚合物中,[Os]为OsCl(PPh3)2,X为CH2或O,R1为芳基取代的乙烯基,优选带有1~28个碳原子的烷基取代的双联芴乙烯基,尤其适用于太阳能电池领域,进一步地,可用作太阳能电池的传输层材料。
优选地,该含锇共轭聚合物中,[Os]为OsCl(PPh3)2,X为CH2或O,R1为芳基取代的乙烯基,优选带有1~28个碳原子的烷基取代的噻吩乙烯噻吩取代的乙烯基,尤其适用于发光二极管领域,进一步地,可用作发光二极管的发光层材料。
本发明的有益效果是:
1.本发明提供的含锇共轭聚合物是一类主链含金属的全新共轭聚合物,其稳定性好,兼具溶解性和加工性。该含锇共轭聚合物不同的连接基团使得该类聚合物的结构变化无穷,为开展性能研究提供了丰富的材料基础。同时该含锇共轭聚合物是一个含dπ-pπ共轭的全新π-共轭聚合物体系,展示出了高摩尔吸光系数以及较好的电化学性能,可广泛应用于太阳能电池、发光二级管,场效应晶体管、化学传感器,化学开关等领域。
2.本发明提供的聚合方法具有合成操作简单、高效专一、条件温和、官能团容忍度高、原子转化效率100%等优点。该方法制备合成的含锇共轭聚合物产率高达99%,Mw分子量高,且分子量分布极窄。
附图说明
图1为本发明实施例1中含锇共轭聚合物1-1的GPC分子量分布图。
图2为本发明实施例1和实施例3中的含锇共轭聚合物1-1和含锇共轭聚合物1-383的紫外-可见吸收光谱图。
具体实施方式
以下将通过具体的实施例对本发明进行详细描述。
以下实施例中,所使用的式M结构的单体金属杂环锇杂戊搭炔化合物按照文献Zhuo,Q.;Lin,J.;Hua,Y.;Zhou,X.;Shao,Y.;Chen,S.;Chen,Z.;Zhu,J.;Zhang,H.;Xia,H.*Multiyne Chains Chelating Osmium via Three MetalcarbonσBonds.Nat.Commun.2017,8,1912.以及Wu,F.;Huang,W.;Zhuo,K.;Hua,Y.;Lin,J.;He,G.;*Chen,J.;Nie,L.;*Xia,H.*Carbolong Complexes as Photothermal Materials.Chin.J.Org.Chem.2019,39,1743-1752.中的方法制备得到。
实施例1
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M1(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有***固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到90毫克***该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.81-7.78(br,53H),6.23(d,J=17.71Hz,1H),5.79(br,2H),3.00(br,2H),2.08(br,2H),1.62(br,2H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=4.57(br,CPPh3),-1.20(br,OsPPh3);
分子量表征数据如下:重均分子量为48227Da,数均分子量为36989Da,该含锇共轭聚合物分子量分布指数为1.30。
本实施例中含锇共轭聚合物1-1的GPC分子量分布见图1。
本实施例中的含锇共轭聚合物1-1的紫外-可见吸收光谱见图2。
实施例2
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M2(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下再反应2小时后,加入大量的***,有紫色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到92毫克***该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.81-7.98(br,53H),6.23(d,J=17.71Hz,1H),5.82(br,2H),5.17(br,2H),4.30(br,2H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=4.57(br,CPPh3),-0.08(br,OsPPh3);
分子量表征数据如下:重均分子量为60383Da,数均分子量为43130Da,该含锇共轭聚合物分子量分布指数为1.40。
实施例3
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M3(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有蓝色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到95毫克该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.83-7.85(br,46H),5.97(d,J=16.38Hz,1H),5.82(br,1H),5.17(br,2H),4.30(br,2H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=4.81(br,CPPh3),-0.08(br,OsPPh3);
分子量表征数据如下:重均分子量为52927Da,数均分子量为39205Da,该含锇共轭聚合物分子量分布指数为1.35。
本实施例中的含锇共轭聚合物1-383的紫外-可见吸收光谱见图2。
实施例4
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M4(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有蓝紫色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到95毫克该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.83-7.85(br,46H),5.97(d,J=17.38Hz,1H),5.82(br,2H),3.01(br,2H),2.07(br,2H),1.65(br,2H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=4.71(br,CPPh3),-0.12(br,OsPPh3);
分子量表征数据如下:重均分子量为58220Da,数均分子量为41005Da,该含锇共轭聚合物分子量分布指数为1.41。
实施例5
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M5(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有紫黑色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到93毫克该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.93-8.31(br,52H),5.84(d,J=16.54Hz,1H),5.17(br,2H),3.73(br,2H),0.70-1.40(br,26H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=4.49(br,CPPh3),-1.58(br,OsPPh3);
分子量表征数据如下:重均分子量为34642Da,数均分子量为29357Da,该含锇共轭聚合物分子量分布指数为1.18。
实施例6
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M6(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有紫黑色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到92毫克该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.48-8.31(br,52H),6.25(br,1H),3.11(br,2H),2.37(br,2H),1.24(br,2H),0.72-1.40(br,26H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=4.13(br,CPPh3),-1.18(br,OsPPh3);
分子量表征数据如下:重均分子量为45633Da,数均分子量为35931Da,该含锇共轭聚合物分子量分布指数为1.27。
实施例7
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M7(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有蓝绿色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到89毫克该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.98-7.87(br,46H),6.08(br,1H),5.19(br,2H),4.39(br,2H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=5.36(s,CPPh3),0.07(s,OsPPh3);
分子量表征数据如下:重均分子量为42622Da,数均分子量为34761Da,该含锇共轭聚合物分子量分布指数为1.23。
实施例8
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M8(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有蓝色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到91毫克该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.98-7.83(br,49H),6.08(br,1H),6.50(q,1H),6.24(d,1H),5.71(q,1H),5.54(d,1H),4.66(br,2H),3.87(br,2H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=5.14(s,CPPh3),-0.23(s,OsPPh3);
分子量表征数据如下:重均分子量为53567Da,数均分子量为40023Da,该含锇共轭聚合物分子量分布指数为1.34。
实施例9
上式中[Os]为OsCl(PPh3)2。其中,HCl·Et2O为盐酸***(购自萨恩化学技术(上海)有限公司,商品牌号为A01W8101821000),(苯乙炔,购自百灵威科技有限公司,商品牌号为445058),所用DCM为二氯甲烷重蒸溶剂。
上述含锇共轭聚合物的制备:在氮气氛围下,在磁力搅拌下,把单体金属杂环锇杂戊搭炔化合物M9(0.1mmol)溶解在5mL的二氯甲烷中,快速加入2mol/L的盐酸***溶剂0.5mL,室温下反应24h后,加入苯乙炔终止反应,室温下反应2小时后,加入大量的***,有蓝色固体化合物析出,过滤,用***反复多次洗涤固体产物,干燥,得到93毫克该含锇共轭聚合物产物。
所得含锇共轭聚合物的结构确认数据如下:1H NMR(600.1MHz,CD2Cl2):δ=6.48-8.31(br,52H),6.25(br,2H),5.97(d,J=18.18Hz,1H),3.12(br,2H),2.36(br,2H),1.22(br,2H),0.72-1.40(br,26H);31P{1H}-NMR(242.9MHz,CD2Cl2):δ=4.98(br,CPPh3),-1.12(br,OsPPh3);
分子量表征数据如下:重均分子量为38978Da,数均分子量为29986Da,该含锇共轭聚合物分子量分布指数为1.30。
以上实施例中的各含锇共轭聚合物的能级信息汇总表详见表1。
表1本发明中含锇共轭聚合物的能级信息汇总表
Samples | EOX[V] | EHOMO[eV] | ERED[V] | ELUMO[eV] |
I-1 | 0.94 | -5.34 | -0.68 | -3.72 |
I-319 | 1.00 | -5.40 | -0.65 | -3.75 |
I-490 | 0.98 | -5.38 | -0.67 | -3.73 |
I-383 | 1.10 | -5.50 | -0.54 | -3.86 |
PC70BM | 1.54 | -5.94 | -0.51 | -3.89 |
以上所述,仅为本发明的较佳实施例而已,故不能依此限定本发明实施的范围,即依本发明专利范围及说明书内容所作的等效变化与修饰,皆应仍属本发明涵盖的范围内。
Claims (3)
2.权利要求1所述的一种含锇共轭聚合物的制备方法,其特征在于:包括步骤:将含锇共轭聚合物的单体溶于有机溶剂中,在酸性条件下进行聚合反应,即得所述含锇共轭聚合物,其反应式如下:
上述酸包括无机酸和有机酸;所述无机酸包括HClO4、HI、HBr、HCl、HNO3、H2SeO4、H2SO4、HClO3、H2C2O4、H2SO3、H3PO4、HNO2、HF、H2CO3、H2S、HClO、H3BO3和H2SiO3;所述有机酸包括CH3SO3H、CF3COOH、CCl3COOH、CHCl2COOH、CH3COOH和HCOOH;
上述有机溶剂包括二氯甲烷、二氯乙烷、氯仿、甲醇、乙醇、丙酮、丁酮、四氢呋喃、二甲基亚砜、N,N-二甲基甲酰胺、甲苯、苯、二氧六环、***和乙腈。
上述聚合反应被2~80个碳原子的取代基取代的末端炔封端终止,该取代基包括取代或未取代的芳基、烷基和环烷基。
3.权利要求1所述的一种含锇共轭聚合物在有机光电器件中的应用。
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