title: A versatile cyclic 2,2'-azobenzenophane with a functional handle and its polymers: efficient synthesis and effect of topological structure on chiroptical properties.
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.
authors.affiliation: 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).
authors.forename: Jinjie
authors.initials: J
authors.lastname: Lu
authors.forename: Aiyou
authors.initials: A
authors.lastname: Xia
authors.forename: Nianchen
authors.initials: N
authors.lastname: Zhou
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Zhengbiao
authors.initials: Z
authors.lastname: Zhang
authors.forename: Xiangqiang
authors.initials: X
authors.lastname: Pan
authors.forename: Yonggang
authors.initials: Y
authors.lastname: Yang
authors.forename: Yong
authors.initials: Y
authors.lastname: Wang
authors.forename: Xiulin
authors.initials: X
authors.lastname: Zhu
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002942:Circular Dichroism; D008968:Molecular Conformation; D009904:Optical Rotation; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D011789:Quantum Theory; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
chemical_list: D001391:Azo Compounds; D011108:Polymers; C009850:azobenzene
keywords: azo compounds; chirality; cyclic compounds; photoisomerization; polymers