基于链接化学策略的固体界面功能化、表征及应用研究
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摘要
链接化学(Click Chemistry)是指利用易得的原料,通过高效、可靠而又具有选择性的反应来实现杂原子连接(C-X-C),从而低成本、快速地合成新化合物的一套实用的合成方法,其反应过程被描述为像点击鼠标一样简单、高效、通用。这类反应具有反应模块化,起始原料或反应物易得,反应操作简单,条件温和,反应收率高,副产物少等优点,被广泛用于组合化学,有机物合成,蛋白质和DNA的标记等领域。
自组装单分子膜(self-sembled monolayer, SAMs)是构膜分子通过分子间及其与基底材料间的物化作用而自发形成的一种热力学稳定、排列规则的单层或多层分子膜。自组装膜技术能在分子水平上设计膜的结构,获得特殊的性能和功能,在电分析领域得到了巨大的应用,成为近年来十分活跃的研究领域。形成SAMs的前体分子的末端官能团决定了材料表面的化学性能。通过可利用的前体分子沉积制备SAMs后,其表面活性基团可以通过化学共价键合的方法进行改性得到系列多样的表面化学性能。
本论文将自组装技术与链接化学策略相结合,对金电极材料进行修饰和改性,通过电化学,光谱学等手段对表面修饰过程进行表征,并将其用于检测,识别和筛选某些目标分析物。
介绍了表面功能化过程中应用较多的化学反应类型和技术,包括Oxime反应,Diels-Alder反应,链接化学,Staudinger反应,Thiol-ene反应,Michael加成反应及光接枝技术。总结了表面功能化过程中的表征技术及其在电分析化学领域的应用。在目前已报道研究成果的基础上,提出了本论文的研究内容和研究意义。
报道了一种多功能的表面化学方法(共价键和的方式),将其用于在金电极自组装膜上配体和蛋白的固载。该策略基于以下两个步骤：1)通过链接反应的方式,终端为炔基(R-C≡CH)的自组装膜与配体叠氮-PEG-氨基(N3-PEG-NH2)结合；2)通过碳二亚胺反应将血红蛋白(Hb)共价固载在配体的氨基端。分别采用表面增强拉曼散射光谱(SERS),原子力扫描电镜(AFM),反射红外吸收光谱(RAIR)以及循环伏安法(CV)来表征该模型界面的反应。同时,研究表明,该界面具有很好的生物兼容性,对较低浓度的过氧化氢具有很好的线性响应。此外,本文研究了血红蛋白氧化还原的热力学特性。
研究了邻苯氢醌,对苯氢醌和多巴胺分别作为亲电试剂,经电化学引发,与金电极表面的自组装单层膜4-巯基嘧啶发生迈克尔加成反应。研究结果表明,三类化合物均可与4-巯基嘧啶迈克尔加成,产物终端氢醌表现出可逆的氧化还原响应,其中邻苯氢醌与4-巯基嘧啶的反应效率最高。此外,研究发现,终端邻苯氢醌与Cu2+和Ni2+合后表现出不同的电化学行为,并且采用电化学和光学手段研究了络合机理。基于终端邻苯氢醌与Cu2+和Ni2+络合后不同的电化学行为,该体系为金属离子的识别提供了一个潜在的平台。
报道了邻苯氢醌修饰金电极,经电化学氧化,端基产物醌与巯基化合物半胱氨酸CYS和谷胱甘肽GSH的亲核加成。通过电化学方法进行监控,该修饰电极能够检测低浓度生理巯基化合物,对半胱氨酸CYS和谷胱甘肽GSH的检测范围分别为1.0×10-9-2.2×10-7 M和1.0×10-9-1.3×10-7 M。此外,研究发现,该修饰电极可用于乙酰胆碱酯酶的活性研究并能够对其抑制剂进行筛选。
Chapter one:Perface
A number of interfacial chemoselective strategies including Oxime reaction, Diels-Alder conjugation, Click chemistry, Staudinger ligation, Thiol-ene reaction, Michael addition, Supermolecular chemistry and Photo-grafting have been developed to immobilize and present a variety of ligands on the surface. Basic concept, characteristic, methods for characterization and applications of surface functionalization are introduced.
Chapter two:High-Quality Covalently Grafting Hemoglobin on Gold Electrodes: Characterization, Redox Thermodynamics and Bio-electrocatalysis
Herein, we report a versatile surface chemistry methodology to covalently immobilize ligands and proteins to self-assembled monolayers (SAMs) on gold electrode. The strategy is based on two steps:1) the coupling of soluble azido-PEG-amimo ligand with an alkynyl-terminated monolayer via click reaction and 2) covalent immobilization hemoglobin (Hb) to the amine-terminated ligand via carbodiimide reaction. Surface-enhanced Raman scattering spectroscopy (SERS), atomic force microscopy (AFM), reflection absorption infrared spectroscopy (RAIR) and cyclic voltammetry are used to characterize the model interfacial reactions. We also demonstrate the excellent biocompatibility of the interface for Hb immobilization and reliable application of the proposed method for H2O2 biosensing. Moreover, the redox thermodynamics of the Fe3+/Fe2+ couple in Hb is also investigated.
Chapter three:Electrochemically Triggered Michael Addition on the Self-Assembly of 4-Thiouracil:Generation of Catechol Terminated Monolayers and Complex with Ni (Ⅱ) and Cu (Ⅱ)
In this paper, catechol,1,4-dihydroxybenzene and dopamine are investigated as precursor of electrophiles for Michael addition reaction with the self-assembled monolayer (SAM) of 4-thiouracil (4-TU) via electrochemical triggering. All compounds can undergo Michael addition reaction with 4-TU, however, only catechol can conduct with high efficiency. The catechol-terminated SAMs via electrochemically triggered Michael addition reaction exhibit reversible redox response. In addition, we find that catechol-terminated SAMs can complex with Ni2+ and Cu2+ with different electrochemical behaviors. Moreover, the mechanism of . complexation of Ni2 +and Cu2+ with catechol-terminated SAMs is also demonstrated with electrochemical and spectrometric methods. Based on the different electrochemical behaviors of Cu2+ and Ni2+ complex, the catechol-terminated SAMs provide a potential platform for metal ions recognition.
Chapter four:Determination of Physiological Thiols by Electrochemical Detection with Catechol-modified Au electrode and Its Application in Inhibitor Screening for Acetylcholinesterase
The nucleophilic addition of the aminothiols cysteine (CYS) and glutathione (GSH) to the electrogenerated o-quinone of Catechol-terminated.SAMs is reported. The modified electrode displayed a good current response to physiological thiols. The linear ranges are 1.0×10-9 to 2.2×10-7M for CYS and 1.0×10-9 to 1.3×10-7M for GSH. Moreover, this method is also useful for activity study and screening inhibitors of AChE.
自组装单分子膜(self-sembled monolayer, SAMs)是构膜分子通过分子间及其与基底材料间的物化作用而自发形成的一种热力学稳定、排列规则的单层或多层分子膜。自组装膜技术能在分子水平上设计膜的结构,获得特殊的性能和功能,在电分析领域得到了巨大的应用,成为近年来十分活跃的研究领域。形成SAMs的前体分子的末端官能团决定了材料表面的化学性能。通过可利用的前体分子沉积制备SAMs后,其表面活性基团可以通过化学共价键合的方法进行改性得到系列多样的表面化学性能。
本论文将自组装技术与链接化学策略相结合,对金电极材料进行修饰和改性,通过电化学,光谱学等手段对表面修饰过程进行表征,并将其用于检测,识别和筛选某些目标分析物。
介绍了表面功能化过程中应用较多的化学反应类型和技术,包括Oxime反应,Diels-Alder反应,链接化学,Staudinger反应,Thiol-ene反应,Michael加成反应及光接枝技术。总结了表面功能化过程中的表征技术及其在电分析化学领域的应用。在目前已报道研究成果的基础上,提出了本论文的研究内容和研究意义。
报道了一种多功能的表面化学方法(共价键和的方式),将其用于在金电极自组装膜上配体和蛋白的固载。该策略基于以下两个步骤：1)通过链接反应的方式,终端为炔基(R-C≡CH)的自组装膜与配体叠氮-PEG-氨基(N3-PEG-NH2)结合；2)通过碳二亚胺反应将血红蛋白(Hb)共价固载在配体的氨基端。分别采用表面增强拉曼散射光谱(SERS),原子力扫描电镜(AFM),反射红外吸收光谱(RAIR)以及循环伏安法(CV)来表征该模型界面的反应。同时,研究表明,该界面具有很好的生物兼容性,对较低浓度的过氧化氢具有很好的线性响应。此外,本文研究了血红蛋白氧化还原的热力学特性。
研究了邻苯氢醌,对苯氢醌和多巴胺分别作为亲电试剂,经电化学引发,与金电极表面的自组装单层膜4-巯基嘧啶发生迈克尔加成反应。研究结果表明,三类化合物均可与4-巯基嘧啶迈克尔加成,产物终端氢醌表现出可逆的氧化还原响应,其中邻苯氢醌与4-巯基嘧啶的反应效率最高。此外,研究发现,终端邻苯氢醌与Cu2+和Ni2+合后表现出不同的电化学行为,并且采用电化学和光学手段研究了络合机理。基于终端邻苯氢醌与Cu2+和Ni2+络合后不同的电化学行为,该体系为金属离子的识别提供了一个潜在的平台。
报道了邻苯氢醌修饰金电极,经电化学氧化,端基产物醌与巯基化合物半胱氨酸CYS和谷胱甘肽GSH的亲核加成。通过电化学方法进行监控,该修饰电极能够检测低浓度生理巯基化合物,对半胱氨酸CYS和谷胱甘肽GSH的检测范围分别为1.0×10-9-2.2×10-7 M和1.0×10-9-1.3×10-7 M。此外,研究发现,该修饰电极可用于乙酰胆碱酯酶的活性研究并能够对其抑制剂进行筛选。
Chapter one:Perface
A number of interfacial chemoselective strategies including Oxime reaction, Diels-Alder conjugation, Click chemistry, Staudinger ligation, Thiol-ene reaction, Michael addition, Supermolecular chemistry and Photo-grafting have been developed to immobilize and present a variety of ligands on the surface. Basic concept, characteristic, methods for characterization and applications of surface functionalization are introduced.
Chapter two:High-Quality Covalently Grafting Hemoglobin on Gold Electrodes: Characterization, Redox Thermodynamics and Bio-electrocatalysis
Herein, we report a versatile surface chemistry methodology to covalently immobilize ligands and proteins to self-assembled monolayers (SAMs) on gold electrode. The strategy is based on two steps:1) the coupling of soluble azido-PEG-amimo ligand with an alkynyl-terminated monolayer via click reaction and 2) covalent immobilization hemoglobin (Hb) to the amine-terminated ligand via carbodiimide reaction. Surface-enhanced Raman scattering spectroscopy (SERS), atomic force microscopy (AFM), reflection absorption infrared spectroscopy (RAIR) and cyclic voltammetry are used to characterize the model interfacial reactions. We also demonstrate the excellent biocompatibility of the interface for Hb immobilization and reliable application of the proposed method for H2O2 biosensing. Moreover, the redox thermodynamics of the Fe3+/Fe2+ couple in Hb is also investigated.
Chapter three:Electrochemically Triggered Michael Addition on the Self-Assembly of 4-Thiouracil:Generation of Catechol Terminated Monolayers and Complex with Ni (Ⅱ) and Cu (Ⅱ)
In this paper, catechol,1,4-dihydroxybenzene and dopamine are investigated as precursor of electrophiles for Michael addition reaction with the self-assembled monolayer (SAM) of 4-thiouracil (4-TU) via electrochemical triggering. All compounds can undergo Michael addition reaction with 4-TU, however, only catechol can conduct with high efficiency. The catechol-terminated SAMs via electrochemically triggered Michael addition reaction exhibit reversible redox response. In addition, we find that catechol-terminated SAMs can complex with Ni2+ and Cu2+ with different electrochemical behaviors. Moreover, the mechanism of . complexation of Ni2 +and Cu2+ with catechol-terminated SAMs is also demonstrated with electrochemical and spectrometric methods. Based on the different electrochemical behaviors of Cu2+ and Ni2+ complex, the catechol-terminated SAMs provide a potential platform for metal ions recognition.
Chapter four:Determination of Physiological Thiols by Electrochemical Detection with Catechol-modified Au electrode and Its Application in Inhibitor Screening for Acetylcholinesterase
The nucleophilic addition of the aminothiols cysteine (CYS) and glutathione (GSH) to the electrogenerated o-quinone of Catechol-terminated.SAMs is reported. The modified electrode displayed a good current response to physiological thiols. The linear ranges are 1.0×10-9 to 2.2×10-7M for CYS and 1.0×10-9 to 1.3×10-7M for GSH. Moreover, this method is also useful for activity study and screening inhibitors of AChE.
引文
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