Polymer, Vol.47, No.1, 435-440, 2006
Polybinaphthyls incorporating chiral (R) or (S)-2,2'-binaphthyl and oxadiazole moieties by Stille reaction
Chiral polymers P-1 and P-2 were prepared by the polymerization of (R)-3,3'-diiodo-2,2'-bisbutoxy- 1, 1'-binaphthyl ((R)-M-1) and (S)-3,3'diiodo-2,2'--bisbutoxy-1,1'-binaphthyl ((S)-M-1) with 2,5-bis[(4-tributylstannyl)phenyl]-1,3,4-oxadiazole (M-2) via Pd(PPh3)(4) catalyzed Stille coupling reaction. 1,3,4-Oxadiazole unit not only has high electron affinity, high thermal and oxidative stability, but also serves as a good chromophore. Polymers have strong blue fluorescence due to the efficient energy migration from the extended pi-electronic structure of the polymers to the chiral binaphthyl core and can be expected to have potential application in the materials of fluorescent sensors. Circular dichroism (CD) spectra of polymers P-1 and P-2 are almost identical except that they gave opposite signals at each wavelength. The long wavelengths CD effect of P-1 and P-2 can be regarded as the more extended conjugated structure in the repeating unit and a high rigidity of the polymer backbone. (c) 2005 Elsevier Ltd. All rights reserved.