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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

, : A versatile cyclic 2,2'-azobenzenophane with a functional handle and its polymers: efficient synthesis and effect of topological structure on chiroptical properties. Chemistry 21(6): 2324-2329

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.


PMID: 25510346

DOI: 10.1002/chem.201405940

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