A Versatile Cyclic 2,2′‐Azobenzenophane with a Functional Handle and Its Polymers: Efficient Synthesis and Effect of Topological Structure on Chiroptical Properties |
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| Authors: | Jinjie Lu Aiyou Xia Prof. Nianchen Zhou Prof. Wei Zhang Prof. Zhengbiao Zhang Dr. Xiangqiang Pan Prof. Yonggang Yang Dr. Yong Wang Prof. Xiulin Zhu |
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| Affiliation: | 1. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application College of Chemistry, Chemical Engineering and Materials Science, Soochow University, No. 199, Ren'ai Road, Industrial Park, Suzhou 215123 (P.R. China);2. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, No. 199, Ren'ai Road, Industrial Park, Suzhou 215123 (P.R. China) |
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| Abstract: | Two novel cyclic azobenzenophanes (SC, RC) with functional handles have been synthesized efficiently by a Glaser coupling reaction. Through a Suzuki coupling reaction, alternating ring/linear polymers with rigid (conjugated)/flexible (unconjugated) bridges were obtained from the resultant cyclic azobenzenophanes. The optical activities of linear, cyclic, and macromolecular binaphethyl–azobenzene derivatives were investigated by UV/Vis and circular dichroism (CD) spectra and the time‐dependent (TD)‐DFT method. Experimental results and theoretical analyses indicated that the cyclic configurations exhibited better chiroptical features than the others, and the reverse conformation and difference of dextro‐/levo‐rotation of azobenzenophanes were detected by comparing linear and cyclic structures, which provides an opportunity for the optical‐rotation‐controlled “smart” materials systems in future. |
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| Keywords: | azo compounds chirality cyclic compounds photoisomerization polymers |
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