水溶性、两性离子、含硼酸的、区域规整头对尾聚噻吩对生物物种的超灵敏荧光响应。

Ultrasensitive fluorescent responses of water-soluble, zwitterionic, boronic acid-bearing, regioregular head-to-tail polythiophene to biological species.

作者信息

Xue Cuihua, Cai Feifei, Liu Haiying

机构信息

Department of Chemistry, Michigan Technological University, Townsend Drive 1400, USA.

出版信息

Chemistry. 2008;14(5):1648-53. doi: 10.1002/chem.200701376.

DOI:10.1002/chem.200701376

PMID:18041796

Abstract

Water-soluble regioregular head-to-tail zwitterionic fluorescent conjugated boronic acid-bearing polythiophene (polymer 2) was prepared through a postpolymerization quaternization of a pyridine group of 3-pyridineboronic acid with bromide groups of regioregular head-to-tail poly(3-bromohexylthiophene) (polymer 1). Titration of monosaccharides, lactose, ascorbic acid, or dopamine with 0.1 M phosphate buffer (pH 7.4), containing 4.0 microM of polymer 2, results in significant concentration-dependent quenching of the polymer fluorescence. The polymer displays an optimum response to the biological species at pH 7.0. The binding constants of polymer 2 with mannose, fructose, glucose, galactose, vitamin C, dopamine, and lactose are 3.33 x 10(4), 1.13 x 10(5), 1.23 x 10(5), 1.69 x 10(5), 3.17 x 10(5), 3.27 x 10(5), and 4.60 x 10(5), respectively.

摘要

通过对区域规整的头-尾聚（3-溴己基噻吩）（聚合物1）的溴基团与3-吡啶硼酸的吡啶基团进行后聚合季铵化反应，制备了水溶性的区域规整的头-尾两性离子型含荧光共轭硼酸的聚噻吩（聚合物2）。用含有4.0微摩尔聚合物2的0.1 M磷酸盐缓冲液（pH 7.4）对单糖、乳糖、抗坏血酸或多巴胺进行滴定，会导致聚合物荧光显著的浓度依赖性猝灭。该聚合物在pH 7.0时对生物物种表现出最佳响应。聚合物2与甘露糖、果糖、葡萄糖、半乳糖、维生素C、多巴胺和乳糖的结合常数分别为3.33×10⁴、1.13×10⁵、1.23×10⁵、1.69×10⁵、3.17×10⁵、3.27×10⁵和4.60×10⁵。