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含三螺吡喃单元大环分子的合成和酸致变色效应
引用本文:周清清,张宪哲,刘和文.含三螺吡喃单元大环分子的合成和酸致变色效应[J].应用化学,2012,29(12):1371-1380.
作者姓名:周清清  张宪哲  刘和文
作者单位:(中国科学院软物质化学重点实验室,中国科学技术大学高分子科学与工程系 合肥 230026)
基金项目:Supported by the National Natural Science Foundation of China(21090354, 21174137)
摘    要:合成了含有3个螺吡喃单元的大环分子,采用点击化学方法实现高效的闭环反应,大环分子产率为64%。 使用红外、核磁和质谱等方法检测和表征了反应中间产物和目标产物,质谱分析结果证实环化结构。 使用紫外-可见光谱仪观察到大环产物和线性螺吡喃前体分子在pH值接近4时的酸致变色效应。 与线性螺吡喃前体分子的最大紫外吸收峰位置(476 nm)相比,螺吡喃大环分子在最大紫外吸收峰位置(464 nm)发生蓝移。 螺吡喃大环分子比线性前体分子具有更大的摩尔消光系数,其pH响应性能更加优异。

关 键 词:大环分子  螺吡喃  点击化学  pH响应  紫外可见吸收  
收稿时间:2012-07-25
修稿时间:2012-10-08

Synthesis and pH-Responsive Chromism of a Macrocyclic Compound with Three Spiropyran Units
ZHOU Qingqing , ZHANG Xianzhe , LIU Hewen.Synthesis and pH-Responsive Chromism of a Macrocyclic Compound with Three Spiropyran Units[J].Chinese Journal of Applied Chemistry,2012,29(12):1371-1380.
Authors:ZHOU Qingqing  ZHANG Xianzhe  LIU Hewen
Institution:(CAS Key Laboratory of Soft Matter Chemistry,Department of Polymer Science and Engineering,; University of Science and Technology of China,Hefei 230026,China)
Abstract:A macrocyclic compound containing three spiropyran subunits(macrocyclic spiropyrans) has been synthesized. Click chemistry has been conducted in a dilute solution to construct the cyclic structure of the target product. The yield of macrocylic compound is 64%. The structure of the macrocyclic compounds is characterized by FT-IR, 1H NMR, 13C NMR and ESI-MS. Cyclization of the macrocyclic spiropyrans is confirmed via MS analysis. The pH-responsive chromic properties of macrocyclic spiropyrans and linear compounds have been studied by using UV-Vis absorption spectroscopy in solutions at pH near 4. The maximum UV-Vis absorption(464 nm) of the macrocylic compound exhibits a blue shift comparing with that of linear compounds(476 nm). It is found that the molar extinction coefficient of the maximum UV-Vis absorption of macrocyclic spiropyrans is greater than those of its linear precursors. Furthermore, macrocyclic spiropyrans shows more sensitive pH-responsivity than its linear precursors.
Keywords:macrocyclic compound  spiropyran  click chemistry  pH-responsive  UV-Vis absorption
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