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A Versatile Cyclic 2,2′‐Azobenzenophane with a Functional Handle and Its Polymers: Efficient Synthesis and Effect of Topological Structure on Chiroptical Properties
Author(s) -
Lu Jinjie,
Xia Aiyou,
Zhou Nianchen,
Zhang Wei,
Zhang Zhengbiao,
Pan Xiangqiang,
Yang Yonggang,
Wang Yong,
Zhu Xiulin
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405940
Subject(s) - optical rotation , azobenzene , conjugated system , circular dichroism , polymer , ring (chemistry) , materials science , topology (electrical circuits) , macromolecule , rotation (mathematics) , chemistry , combinatorial chemistry , crystallography , mathematics , organic chemistry , biochemistry , geometry , combinatorics
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.