SYNTHESIS OF CHIRAL CONJUGATED POLYBINAPHTHYLS BY SONOGASHIRA REACTION

Chiral polymers P-1 and P-2 were synthesized by the polymerization of (R)-3,3'-diiodo-2,2'-bisbutoxy-1,l'-binaphthyl (M-1) with 2,5-di(4-ethynylphenyl)-1,3,4-oxadiazole (M-3) and (R)-3,3'-diethylnyl-2,2'-bisbutoxy-1,1'-binaphthyl (M-2) with 1,2-di(4-bromophenyl)acetylene (M-4) under Sonogashira reaction, respectively. Both monomers and polymers were analyzed by NMR, MS, FT-IR, UV-Vis spectroscopy, DSC-TGA, fluorescence spectroscopy, GPC and CD spectroscopy. CD spectra of P-1 and P-2 are similar due to the same chiral center units and main chain structure. The long wavelengths CD effect of P-1 and P-2 can be regarded as the more extended conjugated structure and a highly rigid backbone in the polymer chain. Polymers have strong blue fluorescence due to the efficient energy migration from the extended π-electronic structure of the polymers to the chiral binaphthyl core and are expected to provide understanding of the relationship between molecular structure and fluorescent property of the chiral polymers.