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Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties
Designed Monomers and Polymers ( IF 1.6 ) Pub Date : 2020-01-01 , DOI: 10.1080/15685551.2020.1796362
Bin-Bin Sun 1, 2 , Bing-Hua Yao 1 , Zheng-Sheng Fu 3 , Yang-Qing He 1
Affiliation  

ABSTRACT 1ʹ-(2-Acryloxyethyl)-3,3ʹ-dimethyl-6-nitrospiro[2 H-1-benzopyran-2,2ʹ-indoline] (SPA) was synthesized and grafted onto a water-soluble carboxymethyl chitin (CMCH) macromolecule to prepare a photochromic copolymer (CMCH-g-SPA). The structure of CMCH-g-SPA was characterized by Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric (TG) analysis, X-ray diffraction (XRD) analysis, water-solubility evaluation, and UV-vis spectroscopy. XRD patterns of CMCH-g-SPA revealed that grafting copolymerization disrupts the CMCH semicrystalline structure, thus improving water solubility. UV-vis spectroscopy results supported the negative photochromic behavior of the merocyanine (MC) form of CMCH-g-SPA (CMCH-g-MCA) present in a water solution of the target copolymer. In addition to high solvent polarity, the intermolecular and intramolecular electrostatic attraction between the indolenine cation and the COO− anion were found to be influencing factors, which stabilize these MC form of spiropyran groups grafted onto CMCH. In a water solution, visible light bleaching was completed over a short period (8 minutes) under artificial visible light irradiation and the thermal coloration reaction, whose rate constant at 25 °C was 4.64 × 10−4 s−1, which fit the first-order reaction equation. After ten photochromic cycles in water solution, the relative absorption intensity of CMCH-g-MCA decreased by 7.92%.

中文翻译:

含有螺吡喃部分的羧甲基甲壳素衍生物光致变色性能的制备与分析

摘要 合成了 1ʹ-(2-Acryloxyethyl)-3,3ʹ-dimethyl-6-nitrospiro[2 H-1-benzopyran-2,2ʹ-indoline] (SPA) 并接枝到水溶性羧甲基甲壳素 (CMCH) 大分子上制备光致变色共聚物(CMCH-g-SPA)。CMCH-g-SPA 的结构通过傅里叶变换红外 (FT-IR) 光谱、热重 (TG) 分析、X 射线衍射 (XRD) 分析、水溶性评估和紫外-可见光谱表征。CMCH-g-SPA 的 XRD 谱显示接枝共聚破坏了 CMCH 半结晶结构,从而提高了水溶性。UV-vis 光谱结果支持存在于目标共聚物的水溶液中的 CMCH-g-SPA (CMCH-g-MCA) 的部花青 (MC) 形式的负光致变色行为。除了高溶剂极性外,发现假吲哚阳离子和 COO− 阴离子之间的分子间和分子内静电吸引力是影响因素,这些因素稳定了接枝到 CMCH 上的螺吡喃基团的 MC 形式。在水溶液中,在人工可见光照射和热显色反应下,在短时间内(8 分钟)完成可见光漂白,其 25 °C 的速率常数为 4.64 × 10−4 s−1,符合第级反应方程式。在水溶液中经过10次光致变色循环后,CMCH-g-MCA的相对吸收强度降低了7.92%。在人工可见光照射和热显色反应下,可见光漂白在短时间内(8分钟)完成,其在25°C时的速率常数为4.64×10-4 s-1,符合一级反应方程式。在水溶液中经过10次光致变色循环后,CMCH-g-MCA的相对吸收强度降低了7.92%。在人工可见光照射和热显色反应下,可见光漂白在短时间内(8分钟)完成,其在25°C时的速率常数为4.64×10-4 s-1,符合一级反应方程式。在水溶液中经过10次光致变色循环后,CMCH-g-MCA的相对吸收强度降低了7.92%。
更新日期:2020-01-01
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