JP2021532899A - ポリアリルグリシジルエーテル基盤の酸化−還元高分子およびそれを用いた電気化学的バイオセンサ - Google Patents
ポリアリルグリシジルエーテル基盤の酸化−還元高分子およびそれを用いた電気化学的バイオセンサ Download PDFInfo
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Abstract
Description
本出願は、2018年9月18日付韓国特許出願第10−2018−0111633号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示されたすべての内容は本明細書の一部として含まれる。
[反応式1]
[反応式2]
RTおよびRLは、それぞれ独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数3〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基、置換または非置換の炭素数3〜30のヘテロアリーレン基、置換または非置換の炭素数2〜40のアルケニル基、置換または非置換の炭素数2〜40のアルキニル基からなる群より選ばれ得、分子量1,000g/mol〜50,000g/molのポリスチレン(PS)、ポリエチレングリコール(PEG or PEO)、ポリメチルメタクリレート(PMMA)、ポリビニルイミダゾール(PVI)、ポリビニルピリジン(PVP)ポリシロキサン(PDMS)のような高分子群より選ばれる。
前記oは10〜300の整数であり;
前記pは0〜300の整数であり;
前記qは10〜300の整数である。
[反応式3]
[反応式4]
[化学式3]
HS−L3−AD3
[化学式4]
MはOs、Rh、Ru、Ir、FeおよびCoからなる群より選ばれる1種の遷移金属であり;
前記式において、LG1およびLG2は互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
LG3およびLG4は、それぞれ互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
LG5およびLG6は、それぞれ互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
[化学式5]
前記R3〜R20は、それぞれ独立して置換または非置換の炭素数1〜10のアルキル基、置換または非置換の炭素数3〜40のシクロアルキル基、置換または非置換の炭素数6〜50のアリール基、置換または非置換の炭素数3〜50のヘテロアリール基、置換または非置換の炭素数1〜20のアルコキシ基、置換または非置換の炭素数1〜20のアルコール基、置換または非置換の炭素数1〜20のアルキルハロゲン基、置換または非置換の炭素数1〜20のチオール基、置換または非置換の炭素数3〜20のアルキルアジド基、置換または非置換の炭素数7〜30のアリールアジド基、置換または非置換の炭素数6〜30のアリールオキシ基、置換または非置換の炭素数1〜20のアルキルアミノ基、置換または非置換の炭素数6〜30のアリールアミノ基、置換または非置換の炭素数1〜20のアルキルシリル基、置換または非置換の炭素数6〜30のアリールシリル基、置換または非置換の炭素数1〜50のアリールアルキルアミノ基、置換または非置換の炭素数2〜40のアルケニル基、置換または非置換の炭素数2〜40のアルキニル基、シアノ基、ハロゲン基、重水素および水素からなる群より選ばれ;
前記L4は、独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数2〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基および置換または非置換の炭素数3〜30のヘテロアリーレン基からなる群より選ばれ、
前記AD4は、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基およびシラン基からなる群より選ばれる。
[反応式4]
[化学式9]
前記oは0〜300の整数であり;
前記pは0〜300の整数であり;
前記qは10〜300の整数である。
前記式において、LG1およびLG2は互いに合わさって前記化学式5〜7から選ばれる二座配位子を形成し;
LG3およびLG4は、それぞれ互いに合わさって前記化学式5〜7から選ばれる二座配位子を形成し;
LG5およびLG6は、それぞれ互いに合わさって前記化学式5〜7から選ばれる二座配位子を形成する。
(a)アリルグリシジルエーテルを開始剤の存在下に重合させてポリアリル−グリシジルエーテル基盤の高分子前駆体を製造する段階;および
(b)前記段階(a)で製造された高分子前駆体にアミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基、およびシラン基からなる群より選ばれる官能基および遷移金属錯体を導入して製造する段階を含む、
ポリアリルグリシジルエーテル基盤の酸化−還元重合体材料の製造方法に関する。
本発明は前記ポリアリルグリシジルエーテル基盤の酸化−還元重合体材料を電極にコートした後、コートされた電極を硬化させる段階を含む、電子伝達媒体の製造方法に関する。
1H NMR (400 MHz, CDCl3): δ 5.93-5.83 (m), 5.27-5.13 (m), 3.98 (br m), 3.64-3.43 (br m), 1.58 (br m), 1.32 br m) (重量回収率: 55%, 5.5 g)
1H NMR (400 MHz, CDCl3): δ 5.93-5.83 (m), 5.27-5.13 (m), 3.98 (br m), 3.64-3.43 (br m), 1.58 (br m), 1.32 br m) (重量回収率: 76%, 18.6 g)
1H NMR (500 MHz, CDCl3): δ 3.60-3.49 (br m), 2.57-2.50 (br m), 1.83 (br m), 1.69 (br m), 1.24-1.20 (br m)
2−2−1:[オスミウム(III)(N,N’−ジメチル−2,2’−ビイミダゾール)2(N−ブチニル−N’−メチル−2,2’−ビイミダゾール)](ヘキサフルオロホスフィン)3の合成(Os−1)
本発明によるポリアリルグリシジルエーテル基盤の重合体および遷移金属錯体としてOs複合体を含む酸化−還元重合体の電子伝達媒体としての性能を確認するために、次のような実験方法により循環電圧電流法を利用して電気化学的特性を測定した。
(1)オスミウム複合体(Os−1,2,3,4,5:PF6陰イオン)は、各20mgを0.1Mテトラブチルアンモニウムパークロレート(Tetrabutylammonium perchlorate)アセトニトリル溶液5mLに溶かし、酸化還元重合体(RP−1,2,3:Cl陰イオン)は各20mgを0.1M塩化ナトリウム(sodium chloride)溶液5mLに溶かした。
作動電極(working electrode):ガラス炭素電極(dia:3.0mm)
基準電極(Reference electrode):Ag/AgCl電極
対向電極(Counter electrode):白金ロッド(Platinum rod)
−装備:EmStat(PalmSens Co.)
−Technique:cyclic voltammetry
−Potential range:−1.0〜1.0 V
−Scan rate:10 mV/s
Claims (24)
- ポリアリルグリシジルエーテル基盤の酸化−還元高分子材料製造用重合体。
- 前記ポリアリルグリシジルエーテルに一級および二級アミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基およびシラン基からなる群より選ばれる機能基が導入された、請求項1に記載の酸化−還元高分子材料製造用重合体。
- 前記重合体は、ポリアリルグリシジルエーテル(PAGE)ホモ重合体、ポリアリルグリシジルエーテル−ポリメチルメタクリレート(PAGE−PMMA)共重合体、ポリアリルグリシジルエーテル−ポリエチレンオキシド(PAGE−PEO)共重合体、ポリアリルグリシジルエーテル−ポリスチレン(PAGE−PS)共重合体、ポリスチレン−ポリアリルグリシジルエーテル−ポリエチレンオキシド(PS−PAGE−PEO)共重合体およびポリメチルメタクリレート−ポリアリルグリシジルエーテル−ポリエチレンオキシド(PMMA−PAGE−PEO)共重合体からなる群より選ばれる重合体を含む、請求項1に記載の酸化−還元高分子材料製造用重合体。
- 下記化学式1または2の構造を有する、請求項1に記載の酸化−還元高分子材料製造用重合体:
[化学式1]
RTおよびRLは、それぞれ独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数3〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基、置換または非置換の炭素数3〜30のヘテロアリーレン基、置換または非置換の炭素数2〜40のアルケニル基、置換または非置換の炭素数2〜40のアルキニル基からなる群より選ばれ;
前記L1〜L2は、それぞれ独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数2〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基および置換または非置換の炭素数3〜30のヘテロアリーレン基からなる群より選ばれ;
前記AD1〜AD2は、一級および二級アミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基およびシラン基からなる群より選ばれ;
前記oは10〜300の整数であり;
前記pは0〜300の整数であり;
前記qは10〜300の整数である。 - 前記RTおよびRLは、それぞれ独立して分子量1,000g/mol〜50,000g/molのポリスチレン(PS)、ポリエチレングリコール(PEG)、ポリエチレンオキシド(PEO)、ポリメチルメタクリレート(PMMA)、ポリビニルイミダゾール(PVI)、ポリビニルピリジン(PVP)およびポリシロキサン(PDMS)からなる群より選ばれる、請求項4に記載の酸化−還元高分子材料製造用重合体。
- 前記機能基は、一級および二級アミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基およびシラン基からなる群より選ばれる機能基を有するチオール系化合物を使用してクリック反応によって導入されたことを特徴とする、請求項2に記載の酸化−還元高分子材料製造用重合体。
- 前記チオール系化合物は、下記化学式3の化合物である、請求項6に記載の酸化−還元高分子材料製造用重合体:
[化学式3]
HS−L3−AD3
前記L3は、独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数3〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基および置換または非置換の炭素数3〜30のヘテロアリーレン基からなる群より選ばれ、
前記AD3は、一級および二級アミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基、およびシラン基からなる群より選ばれる。 - 1,000g/mol〜500,000g/mol範囲の重量平均分子量を有する、請求項1に記載の酸化−還元高分子材料製造用重合体。
- 請求項1ないし8のいずれか一項による重合体を含む、電気化学的センサ用酸化−還元高分子材料。
- 前記重合体に一級および二級アミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基、およびシラン基からなる群より選ばれる機能基および遷移金属錯体が結合されたことを特徴とする、請求項9に記載の酸化−還元高分子材料。
- 前記遷移金属錯体は、下記化学式4の構造を有する、請求項10に記載の酸化−還元高分子材料:
[化学式4]
MはOs、Rh、Ru、Ir、FeおよびCoからなる群より選ばれる1種の遷移金属であり;
前記式において、LG1およびLG2は互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
LG3およびLG4は、それぞれ互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
LG5およびLG6は、それぞれ互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
[化学式5]
前記R3〜R20は、それぞれ独立して置換または非置換の炭素数1〜10のアルキル基、置換または非置換の炭素数3〜40のシクロアルキル基、置換または非置換の炭素数6〜50のアリール基、置換または非置換の炭素数3〜50のヘテロアリール基、置換または非置換の炭素数1〜20のアルコキシ基、置換または非置換の炭素数1〜20のアルコール基、置換または非置換の炭素数1〜20のアルキルハロゲン基、置換または非置換の炭素数1〜20のチオール基、置換または非置換の炭素数3〜20のアルキルアジド基、置換または非置換の炭素数7〜30のアリールアジド基、置換または非置換の炭素数6〜30のアリールオキシ基、置換または非置換の炭素数1〜20のアルキルアミノ基、置換または非置換の炭素数6〜30のアリールアミノ基、置換または非置換の炭素数1〜20のアルキルシリル基、置換または非置換の炭素数6〜30のアリールシリル基、置換または非置換の炭素数1〜50のアリールアルキルアミノ基、置換または非置換の炭素数2〜40のアルケニル基、置換または非置換の炭素数2〜40のアルキニル基、シアノ基、ハロゲン基、重水素および水素からなる群より選ばれ;
前記L4は、独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数2〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基、および置換または非置換の炭素数3〜30のヘテロアリーレン基からなる群より選ばれ;
前記AD4は、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基およびシラン基からなる群より選ばれる。 - 前記遷移金属錯体は、アミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基、およびシラン基からなる群より選ばれる機能基として機能化された、請求項10に記載の酸化−還元高分子材料。
- 下記化学式9または10の構造を有する、請求項10に記載の酸化−還元重合体材料:
[化学式9]
RTおよびRLは、それぞれ独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数3〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基、置換または非置換の炭素数3〜30のヘテロアリーレン基、置換または非置換の炭素数2〜40のアルケニル基、置換または非置換の炭素数2〜40のアルキニル基からなる群より選ばれ;
前記L1〜L2は、それぞれ独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数3〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基、置換または非置換の炭素数3〜30のヘテロアリーレン基からなる群より選ばれ;
前記AD1は、一級および二級アミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基およびシラン基からなる群より選ばれ;
前記oは0〜300の整数であり;
前記pは0〜300の整数であり;
前記qは10〜300の整数である。
MはOs、Rh、Ru、Ir、FeおよびCoからなる群より選ばれる1種の遷移金属であり;
前記式において、LG1およびLG2は互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
LG3およびLG4は、それぞれ互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
LG5およびLG6は、それぞれ互いに合わさって下記化学式5〜7から選ばれる二座配位子を形成し;
[化学式5]
前記R3〜R20は、それぞれ独立して置換または非置換の炭素数1〜10のアルキル基、置換または非置換の炭素数3〜40のシクロアルキル基、置換または非置換の炭素数6〜50のアリール基、置換または非置換の炭素数3〜50のヘテロアリール基、置換または非置換の炭素数1〜20のアルコキシ基、置換または非置換の炭素数1〜20のアルコール基、置換または非置換の炭素数1〜20のアルキルハロゲン基、置換または非置換の炭素数1〜20のチオール基、置換または非置換の炭素数3〜20のアルキルアジド基、置換または非置換の炭素数7〜30のアリールアジド基、置換または非置換の炭素数6〜30のアリールオキシ基、置換または非置換の炭素数1〜20のアルキルアミノ基、置換または非置換の炭素数6〜30のアリールアミノ基、置換または非置換の炭素数1〜20のアルキルシリル基、置換または非置換の炭素数6〜30のアリールシリル基、置換または非置換の炭素数1〜50のアリールアルキルアミノ基、置換または非置換の炭素数2〜40のアルケニル基、置換または非置換の炭素数2〜40のアルキニル基、シアノ基、ハロゲン基、重水素および水素からなる群より選ばれ;
前記L4は、独立して置換または非置換の炭素数1〜20のアルキレン基、置換または非置換の炭素数1〜20のシクロアルキレン基、置換または非置換の炭素数2〜30のエチレングリコール基、置換または非置換の炭素数6〜30のアリーレン基および置換または非置換の炭素数3〜30のヘテロアリーレン基からなる群より選ばれ;
Xはトリアゾール基、エーテル、チオエーテル、アミド基、ウレア基、ウレタン基またはシラン基のような官能基を含む群より選ばれる。 - (a)アリルグリシジルエーテルを開始剤の存在下に重合させてポリアリルグリシジルエーテル基盤の高分子前駆体を製造する段階;および
(b)前記段階(a)で製造された高分子前駆体にアミン基、アンモニウム基、ハロゲン基、エポキシ基、アジド基、アクリレート基、アルケニル基、アルキニル基、チオール基、イソシアネート、アルコール基、およびシラン基からなる群より選ばれる官能基および遷移金属錯体を導入して製造する段階を含む、
請求項9によるポリアリルグリシジルエーテル基盤の酸化−還元重合体材料の製造方法。 - 請求項9によるポリアリルグリシジルエーテル基盤の酸化−還元重合体材料を電極にコートした後、コートされた電極を硬化させる段階を含む、電子伝達媒体の製造方法。
- 請求項16による製造方法によって製造された、電子伝達媒体。
- 請求項16による製造方法によって製造された電子伝達媒体を含む、電気化学的バイオセンサ。
- 液体性生体試料を酸化還元させることができる酵素;および
請求項16による製造方法によって製造された電子伝達媒体を含む、電気化学的バイオセンサ用センシング膜。 - 前記酵素は、
脱水素酵素(dehydrogenase)、酸化酵素(oxidase)、およびエステル化酵素(esterase)からなる群より選ばれた1種以上の酸化還元酵素;または
脱水素酵素、酸化酵素、およびエステル化酵素からなる群より選ばれた1種以上の酸化還元酵素とフラビンアデニンジヌクレオチド(flavin adenine dinucleotide,FAD)、ニコチンアミドアデニンジヌクレオチド(nicotinamide adenine dinucleotide,NAD)、およびピロロキノリンキノン(Pyrroloquinoline quinone,PQQ)からなる群より選ばれた1種以上の補助因子を含む、請求項19に記載の電気化学的バイオセンサ用センシング膜。 - 前記酸化還元酵素は、37℃緩衝溶液で1週間70%以上の活性度を維持できるグルコース脱水素酵素である、請求項20に記載の電気化学的バイオセンサ用センシング膜。
- カーボンナノチューブをさらに含む、請求項19に記載の電気化学的バイオセンサ用センシング膜。
- 請求項19による電気化学的バイオセンサ用センシング膜を含む、電気化学的バイオセンサ。
- 前記センサは、持続血糖モニタリングセンサである、請求項23に記載の電気化学的バイオセンサ。
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