Synthesis and pH-Responsive Chromism of a Macrocyclic Compound with Three Spiropyran Units

doi:10.3724/SP.J.1095.2012.20329

Chinese Journal of Applied Chemistry

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Synthesis and pH-Responsive Chromism of a Macrocyclic Compound with Three Spiropyran Units

ZHOU Qingqing, ZHANG Xianzhe, LIU Hewen^*

(CAS Key Laboratory of Soft Matter Chemistry,Department of Polymer Science and Engineering,
University of Science and Technology of China,Hefei 230026,China)

Received:2012-07-25 Revised:2012-10-08 Published:2012-12-10 Online:2012-12-10
Contact: Hewen Liu
About author:LIU Hewen, professor; Tel/Fax:0551-3607780; E-mail:lhewen@ustc.edu.cn; Research Interests: synthesis of functional polymer and polymer nanomaterials

Abstract

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.

Key words: macrocyclic compound, spiropyran, click chemistry, pH-responsive, UV-Vis absorption

CLC Number:

O633

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, DOI: 10.3724/SP.J.1095.2012.20329.

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Synthesis and pH-Responsive Chromism of a Macrocyclic Compound with Three Spiropyran Units

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