School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
College of Textile Garment, Southwest University, 400715, China.
Carbohydr Polym. 2023 Jan 1;299:120183. doi: 10.1016/j.carbpol.2022.120183. Epub 2022 Oct 3.
It is a challenge to achieve the fully water-soluble chitosan. In this work, water-soluble chitosan-based probes were obtained by the following steps: boron-dipyrrolemethene (BODIPY)-OH was synthesized, and then BODIPY-OH was halogenated to BODIPY-Br. Afterwards, BODIPY-Br reacted with carbon disulfide and mercaptopropionic acid to obtain BODIPY-disulfide. BODIPY-disulfide was introduced to chitosan via amidation reaction to obtain fluorescent chitosan-thioester (CS-CTA); it is employed as the macro-initiator. Methacrylamide (MAm) was grafted onto chitosan fluorescent thioester through reversible addition-fragmentation chain transfer (RAFT) polymerization method. Thus, a water-soluble macromolecular probe (CS-g-PMAm) with chitosan as the main chain and PMAm as long-branched chains was obtained. It greatly improved the solubility in pure water. The thermal stability was reduced slightly, and the stickiness was greatly reduced and the samples displayed the characteristics of liquid. CS-g-PMAm could detect Fe in pure water. By the same method, CS-g-PMAA (CS-g-Polymethylacrylic acid) was synthesized and investigated as well.
实现完全水溶性壳聚糖具有一定的挑战性。在这项工作中，通过以下步骤得到了基于水溶性壳聚糖的探针：合成了硼二吡咯甲川（BODIPY）-OH，然后将 BODIPY-OH 卤化得到 BODIPY-Br。接着，BODIPY-Br 与二硫化碳和巯基丙酸反应得到 BODIPY-二硫键。BODIPY-二硫键通过酰胺化反应被引入壳聚糖中，得到荧光壳聚糖硫酯（CS-CTA）；它被用作大分子引发剂。通过可逆加成-断裂链转移（RAFT）聚合方法，将丙烯酰胺（MAm）接枝到壳聚糖荧光硫酯上。因此，得到了一种以壳聚糖为主链、PMAm 为长支链的水溶性大分子探针（CS-g-PMAm）。这大大提高了其在纯水中的溶解度。热稳定性略有降低，粘性大大降低，样品呈现出液体的特性。CS-g-PMAm 可以在纯水中检测 Fe。通过相同的方法，还合成并研究了 CS-g-PMAA（CS-g-聚丙烯酸）。
