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Citation: 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. doi: 10.3724/SP.J.1095.2012.20329 shu

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

1.
CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China

Corresponding author: LIU Hewen,
Received Date: 25 July 2012
Available Online: 8 October 2012

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.
- macrocyclic compound,
- spiropyran,
- click chemistry,
- pH-responsive,
- UV-Vis absorption
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