Polymer, Vol.47, No.8, 2596-2602, 2006
Stimuli-responsive conjugated polymers. Synthesis and chiroptical properties of polyacetylene carrying L-glutamic acid and azobenzene in the side chain
A glutamic acid- and azobenzene-containing novel N-propargylamide. (S)-CH CCH2NHCOCH(CH2NCOCH(CH2CH2CO2CH2C6H5)NHCO2CH2CH2-p-C6H4N=NC6H5 (1) was synthesized and polymerized with (nbd)Rh+[eta(6)-C6H5B-(C6H5)(3)] as a catalyst to obtain the corresponding polymer [poly(1)] with the moderate number-average molecular weight of 12,200 in 93% yield. The chiroptical studies revealed that poly(l) took a helical structure in THF, CHCl3, CH2Cl2 and toluene. Poly(1) underwent solvent and heat-driven helix-helix transition. The trans-azobenzene of the side chain isomerized into cis upon UV-irradiation, accompanying decrease in helicity. The cis-azobenzene moiety reisomerized into trans upon visible-light irradiation, while the polymer did not recover the original helicity. (c) 2006 Elsevier Ltd. All rights reserved.