Sugar–Poly(para‐phenylene ethynylene) Conjugates as Sensory Materials: Efficient Quenching by Hg²⁺ and Pb²⁺ Ions

Abstract

Three polar poly(para-phenylene ethynylene)s (PPE) were synthesized by utilizing the Heck-Sonogashira protocol. Two of the PPEs carry beta-glucopyranose substituents. Depending upon the linker used between the glycol units and the backbone, the fluorescence of these PPEs can be quenched by Hg2+ and Pb2+ to a varying degree. Monomeric model compounds that are substituted with only one glucose unit are not efficiently quenched. The presence of many glucose substituents in one PPE assembly led to a large increase in the binding constant to Hg2+ and quenching of the fluorescence was amplified.

Synthesis and optical properties of poly(phenylenethiophene)s bearing conjugated side chains

“…Various designs of the chemical structures of conjugated polymers have been studied to achieve improved performances. Since a conjugated structure consists of rigid structure, alkoxyl groups [5], or ethylene glycol [6,7] introduced into the main chains have been reported in order to obtain solubility and processability. Design of conjugated backbones is considered to draw optical and electrical functionalities.…”

Triphenylamine-based fluorescent conjugated glycopolymers: Synthesis, characterization and interactions with lectins

“…In particular, fluorescent conjugated glycopolymers that possess both fluorescent scaffolding and reporting carbohydrate ligands are attractively used in carbohydrate-protein interaction studies and biosensor applications because of their intrinsic optical properties, high sensitivities to minor stimuli, and good biocompatibilities [9][10][11][12][13]. A few conjugated polymers, such as polythiophene [10,11], polyfluorene [12], poly(p-phenylene-ethynylene) [13][14][15][16][17], poly(phenylene-vinylene) [18], and poly(p-phenylene) [19], have been chosen to design this type of multivalent glycoconjugates. One approach to such a system is represented by the polymerization or copolymerization of well-defined carbohydrate-carrying monomers through classical C-C coupling reactions [10,13,[15][16][17][18].…”

“…A few conjugated polymers, such as polythiophene [10,11], polyfluorene [12], poly(p-phenylene-ethynylene) [13][14][15][16][17], poly(phenylene-vinylene) [18], and poly(p-phenylene) [19], have been chosen to design this type of multivalent glycoconjugates. One approach to such a system is represented by the polymerization or copolymerization of well-defined carbohydrate-carrying monomers through classical C-C coupling reactions [10,13,[15][16][17][18]. Another synthetic approach is the so-called postpolymerization functionalization, in which sugar moieties are grafted to the backbones after the formation of conjugated polymers [11,12,14,19].…”

Biotinylated Water-Soluble Conjugated Polymers：Synthesis and the Application in Biological Analysis

“…相比 而言, 生物功能化的水溶性共轭聚合物, 则可以通过受 体-配体之间的特异性反应来提高生物分子检测的选择 性和成像分析的靶向性. 目前, 已报道的水溶性共轭聚 合物的功能化基团主要为糖基 [15] 、 羧基 [16,17] 和氨基 [18,19] , 侧链修饰生物素 [20] 、氨基酸 [21] 、肽段 [22] 、核酸 [23] 或抗 体 [24] 等生物分子的功能化共轭聚合物还比较少 [25] . Figure 3 Responses of UV-visible absorbance (A) and fluorescence emission (B) to the concentration of PFPNBr-biotin 时, SA 的加入会使聚合物的荧光显著猝灭, 而对照蛋白 图 5 (A) pH 分别为 5, 7, 9 的体系中对蛋白的检测、(B) pH 为 7 时 NaCl 浓度对 SA 蛋白检测的影响和(C) pH 为 9 时 NaCl 浓度对 SA 蛋 白检测的影响 Figure 5 Detection of proteins with PFPNBr-biotin in solutions with pHs 5, 7 and 9 (A), influence of NaCl concentration on protein detection in solution of pH 7 (B) and pH 9 (C) BSA 对其荧光几乎没有影响, 因此在两种条件下都能 很好的识别靶蛋白.…”