JP2014515773A - 薄膜コーティング用ポリマー - Google Patents
薄膜コーティング用ポリマー Download PDFInfo
- Publication number
- JP2014515773A JP2014515773A JP2014502554A JP2014502554A JP2014515773A JP 2014515773 A JP2014515773 A JP 2014515773A JP 2014502554 A JP2014502554 A JP 2014502554A JP 2014502554 A JP2014502554 A JP 2014502554A JP 2014515773 A JP2014515773 A JP 2014515773A
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- Prior art keywords
- thin film
- electrode
- metal
- solution
- carbon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000010409 thin film Substances 0.000 title claims description 60
- 229920000642 polymer Polymers 0.000 title abstract description 67
- 238000009501 film coating Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 14
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 14
- 239000004065 semiconductor Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229940074360 caffeic acid Drugs 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 9
- 235000004883 caffeic acid Nutrition 0.000 claims description 9
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 9
- -1 NH 2 Chemical group 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 150000001345 alkine derivatives Chemical class 0.000 claims description 7
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 6
- 108091023037 Aptamer Proteins 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 6
- 108020004414 DNA Proteins 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000427 antigen Substances 0.000 claims description 6
- 108091007433 antigens Proteins 0.000 claims description 6
- 102000036639 antigens Human genes 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 6
- 235000014633 carbohydrates Nutrition 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- 238000002848 electrochemical method Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000012634 fragment Substances 0.000 claims description 6
- 150000002632 lipids Chemical class 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- 108090000623 proteins and genes Proteins 0.000 claims description 6
- 102000004169 proteins and genes Human genes 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 235000000346 sugar Nutrition 0.000 claims description 6
- 150000001923 cyclic compounds Chemical class 0.000 claims description 5
- 239000007858 starting material Substances 0.000 abstract description 53
- 230000004048 modification Effects 0.000 abstract description 12
- 238000012986 modification Methods 0.000 abstract description 12
- 230000008901 benefit Effects 0.000 abstract description 7
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- 238000000053 physical method Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 21
- 229910021397 glassy carbon Inorganic materials 0.000 description 15
- 229920000547 conjugated polymer Polymers 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000002484 cyclic voltammetry Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 4
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000276 potassium ferrocyanide Substances 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000008275 binding mechanism Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000006056 electrooxidation reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 0 C*(C)CCN(CCN)CCNCCN(CCNCCN)CCN(CCNCCC(C)(C)C)CCN(CCN)CCN Chemical compound C*(C)CCN(CCN)CCNCCN(CCNCCN)CCN(CCNCCC(C)(C)C)CCN(CCN)CCN 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920001688 coating polymer Polymers 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- 238000012544 monitoring process Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
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Abstract
Description
nは、1を超える任意の整数であり;
R1及び/又はR2は、H、アルキル、アルケン、アルキン(アルキルの場合は炭素原子の数は1〜4個、アルケンの場合は2〜6個、アルキンの場合は2〜6個である)、OH、Br、Cl、I、F、SH、COOH、NH2、CHO、マレイミド、NHSエステル、金属錯体を形成することができる複素環式化合物、炭水化物、タンパク質、ペプチド、DNA、RNA、抗体、抗原、酵素、細菌、レドックス分子、ホスト分子、ゲスト分子、ハプテン、脂質、微生物、アプタマー、又は糖であり;R1はR2と同一であるか又は異なっていてもよく、R1及びR2のうち少なくとも1つはNH2、COOH、OH又はSHである。
nは1を超える任意の整数であり;
R1及び/又はR2は、H、アルキル、アルケン、アルキン、OH、Br、Cl、I、F、SH、COOH、NH2、CHO、マレイミド、NHSエステル、金属錯体を形成することができる複素環式化合物、他の適用できる官能基、炭水化物、タンパク質、ペプチド、DNA、RNA、抗体、抗原、酵素、細菌、レドックス分子、ホスト分子、ゲスト分子、ハプテン、脂質、微生物、アプタマー、又は糖であり;及び
R1はR2と同一であるか又は異なっていてもよく、R1及びR2のうち少なくとも1つはNH2、COOH、OH、又はSHである。
下記のスキーム1は、ポリマー出発物質1による電極表面の修飾を例示する。いかなる特定の理論にも拘束されることを望むものではないが、ポリマー出発物質1がグルコース部分の−OH基の酸素原子を介して所与の表面に結合することが考えられる。他の結合メカニズム(複素環の部分のN及び/又はS分子又は共役ポリマー骨格のCを介した結合など)も考えられ得る。
下記のスキーム2は、ポリマー出発物質2による電極表面の修飾を例示している。いかなる特定の理論にも拘束されることを望むものではないが、ポリマー出発物質2がアミン側鎖の窒素原子を介して所与の表面に結合することが考えられる。他の結合メカニズム(ポリマー鎖中の窒素原子を介した結合など)も考えられ得る。
下記のスキーム3は、最終的な薄膜がコーヒー酸分子の少なくとも1つのフラグメントを含むように、実施例2の修飾電極表面をコーヒー酸により更に修飾したものを例示している。フラグメントは、電極による電子移動を介してレドックス反応を受けることができる部分として特徴づけられる。
Claims (46)
-
前記式中、
nは1を超える任意の整数であり、
R1及び/又はR2は、H、アルキル、アルケン、アルキン、OH、Br、Cl、I、F、SH、COOH、NH2、CHO、マレイミド、NHSエステル、金属錯体を形成することができる複素環式化合物、炭水化物、タンパク質、ペプチド、DNA、RNA、抗体、抗原、酵素、細菌、レドックス分子、ホスト分子、ゲスト分子、ハプテン、脂質、微生物、アプタマー又は糖であり、
R1はR2と同一であるか又は異なっていてもよく、
R1及びR2のうち少なくとも1つはNH2、COOH、OH又はSHである薄膜。 - 約1nm〜約1μmの厚さを有する請求項1に記載の薄膜。
- 炭素、少なくとも1種の金属又は少なくとも1種の半導体を含む表面と組み合わせた請求項1に記載の薄膜を含む組成物。
- 前記表面が炭素電極又は金属電極である請求項3に記載の組成物。
- 電気化学的方法によって付着させる請求項1に記載の薄膜。
- 約1nm〜約1μmの厚さを有する、請求項6に記載の薄膜。
- 炭素を含む表面、少なくとも1種の金属を含む表面又は少なくとも1種の半導体を含む表面と組み合わせた請求項6に記載の薄膜を含む組成物。
- 前記表面が炭素電極、金属電極、又は半導体電極である請求項8に記載の組成物。
- 電気化学的方法によって付着させる請求項6に記載の薄膜。
-
前記式中、
nは1を超える任意の整数であり、
R1及び/又はR2は、H、アルキル、アルケン、アルキン、OH、Br、Cl、I、F、SH、COOH、NH2、CHO、マレイミド、NHSエステル、金属錯体を形成することができる複素環式化合物、炭水化物、タンパク質、ペプチド、DNA、RNA、抗体、抗原、酵素、細菌、レドックス分子、ホスト分子、ゲスト分子、ハプテン、脂質、微生物、アプタマー又は糖であり、
R1はR2と同一であるか又は異なっていてもよく、
R1及びR2のうち少なくとも1つはNH2、COOH、OH又はSHである薄膜。 - 約1nm〜約1μmの厚さを有する請求項12に記載の薄膜。
- 炭素を含む表面又は少なくとも1種の金属を含む表面と組み合わせた請求項12に記載の薄膜を含む組成物。
- 前記表面が炭素電極又は金属電極である請求項14に記載の組成物。
- 前記薄膜を電気化学的方法によって付着させる請求項14に記載の組成物。
- コーヒー酸分子の少なくとも1つのフラグメントを更に含む請求項12に記載の薄膜。
- 約1nm〜約1μmの厚さを有する請求項19に記載の薄膜。
- 炭素を含む表面、少なくとも1種の金属を含む表面又は少なくとも1種の半導体を含む表面を組み合わせた請求項19に記載の薄膜を含む組成物。
- 前記表面が炭素電極又は金属電極である請求項21に記載の組成物。
- 電気化学的方法によって付着させる請求項21に記載の薄膜。
- コーヒー酸分子の少なくとも1つのフラグメントを更に含む請求項19に記載の薄膜。
- 薄膜を作製する方法であって:
1)
nは1を超える任意の整数であり、
R1及び/又はR2は、H、アルキル、アルケン、アルキン、OH、Br、Cl、I、F、SH、COOH、NH2、CHO、マレイミド、NHSエステル、金属錯体を形成することができる複素環式化合物、炭水化物、タンパク質、ペプチド、DNA、RNA、抗体、抗原、酵素、細菌、レドックス分子、ホスト分子、ゲスト分子、ハプテン、脂質、微生物、アプタマー又は糖であり、
R1はR2と同一であるか又は異なっていてもよく、
R1及びR2のうち少なくとも1つはNH2、COOH、OH、又はSHである。)
のうち1つを含む溶液を調製することと;
2)前記溶液中に少なくとも1つの表面を浸漬することと;
3)電気化学的信号を前記溶液に印加することと;
4)前記表面上に少なくとも1つの薄膜又はコーティングを形成させることと、を含む方法。 - 前記薄膜が約1nm〜約1μmの厚さを有する請求項25に記載の方法。
- 前記表面が炭素、少なくとも1種の金属又は少なくとも1種の半導体を含む請求項25に記載の方法。
- 前記表面が炭素電極、金属電極又は半導体電極である請求項27に記載の方法。
- 電気化学的信号の印加は、電圧、電圧走査又は電流の印加を含む請求項27に記載の方法。
- 前記薄膜が約1nm〜約1μmの厚さを有する請求項30に記載の方法。
- 前記表面が炭素、少なくとも1種の金属又は少なくとも1種の半導体を含む請求項30に記載の方法。
- 前記表面が炭素電極、金属電極又は半導体電極である請求項30に記載の方法。
- 電気化学的信号の印加は、電圧、電圧走査又は電流の印加を含む請求項30に記載の方法。
- 薄膜を作製する方法であって:
1)
nは1を超える任意の整数であり、
R1及び/又はR2は、H、アルキル、アルケン、アルキン、OH、Br、Cl、I、F、SH、COOH、NH2、CHO、マレイミド、NHSエステル、金属錯体を形成することができる複素環式化合物、炭水化物、タンパク質、ペプチド、DNA、RNA、抗体、抗原、酵素、細菌、レドックス分子、ホスト分子、ゲスト分子、ハプテン、脂質、微生物、アプタマー又は糖であり、
R1はR2と同一であるか又は異なっていてもよく、
R1及びR2のうち少なくとも1つはNH2、COOH、OH、又はSHである。)
を含む溶液を調製することと;
2)前記溶液中に少なくとも1つの表面を浸漬することと;
3)電気化学的信号を前記溶液に印加することと;
4)前記表面上に少なくとも1つの薄膜又はコーティングを形成させることと、
を含む方法。 - 前記薄膜が約1nm〜約1μmの厚さを有する請求項36に記載の方法。
- 前記表面が炭素、少なくとも1種の金属又は少なくとも1種の半導体を含む請求項36に記載の方法。
- 前記表面が炭素電極、金属電極又は半導体電極である請求項36に記載の方法。
- 電気化学的信号の印加は、電圧、電圧走査又は電流の印加を含む請求項36に記載の方法。
- 前記薄膜がコーヒー酸分子の少なくとも1つのフラグメントを更に含む請求項36に記載の方法。
- 前記薄膜が約1nm〜約1μmの厚さを有する請求項42に記載の方法。
- 前記表面が炭素、少なくとも1種の金属又は少なくとも1種の半導体を含む請求項42に記載の方法。
- 前記表面が炭素電極、金属電極又は半導体電極である請求項42に記載の方法。
- 電気化学的信号の印加は、電圧、電圧走査又は電流の印加を含む請求項42に記載の方法。
- 前記薄膜がコーヒー酸分子の少なくとも1つのフラグメントを更に含む請求項42に記載の方法。
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- 2012-03-28 WO PCT/US2012/000173 patent/WO2013058803A1/en active Application Filing
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EP2691961A1 (en) | 2014-02-05 |
US20140011010A1 (en) | 2014-01-09 |
EP2691961A4 (en) | 2015-04-29 |
WO2013058803A1 (en) | 2013-04-25 |
US9018344B2 (en) | 2015-04-28 |
JP5889393B2 (ja) | 2016-03-22 |
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