A versatile cyclic 2,2'-azobenzenophane with a functional handle and its polymers: efficient synthesis and effect of topological structure on chiroptical properties.

Chemistry

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).

Published: February 2015

AI Article Synopsis

  • Two new cyclic azobenzenophanes (SC, RC) with functional handles were created using a Glaser coupling reaction.
  • Through a subsequent Suzuki coupling reaction, researchers produced alternating ring/linear polymers featuring rigid and flexible components.
  • Optical activity analysis via UV/Vis, circular dichroism, and theoretical methods showed that cyclic structures displayed superior chiroptical properties, suggesting potential applications in "smart" materials that respond to optical rotation.

Article 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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http://dx.doi.org/10.1002/chem.201405940DOI Listing

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