Synthesis and chiroptical properties of optically active poly(<i>N</i>‐propargylamide) bearing photoisomerizable azobenzene moieties

Abstract

Abstract A chiral azobenzene‐containing N ‐propargylamide monomer, that is, ( R )‐2‐(4‐phenylazophenoxy)‐ n ‐prop‐2‐ynyl‐propionamide, was prepared and polymerized in the presence of a rhodium catalyst to yield an optically active polyacetylene. The 1 H NMR analysis of the polymer indicated a predominant cis structure of the backbone (cis concentration = 80%); and the chiroptical property studies showed an enhanced optical rotatory power and a strong Cotton effect, indicating the formation of a secondary helical conformation. A reversible optical modulation of chiroptical properties of the polymer due to the reversible photoisomerization of the azobenzene was observed. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 6047–6054, 2006