POLYBINAPHTHYLS INCORPORATING (R)-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES

Chiral polymer was synthesized by the polymerization of （R）-6,6＇-bistributylstannyl-2,2＇-binaphtho-20-crown-6 （M-1） with 1,4-dibromo-2,3-bisbutoxy-naphthyl （M-2） by Pd（PPhs）4 catalyzed Stille coupling reaction. Both monomer and polymer were analyzed by NMR, MS, FT-IR, UV, polarimetry, DSC-TGA, CD, fluorescent spectroscopy and GPC. The major difference between monomer and polymer is that a long wavelength Cotton Effect was observed for the polymer due to its more extended conjugation in the repeating unit and a highly rigid backbone in the polymer chain. Polymer has strong blue fluorescence due to the efficient energy migration from the extended n-electronic structure of the repeating unit of the polymer to the chiral binaphthyl core and is expected to have potential application in the materials of fluorescent sensors and chiral chromatographic packing for resolution ofracemic amino acid.

POLYBINAPHTHYLS INCORPORATING (R)-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES

 Chiral polymer was synthesized by the polymerization of (R)-6,6'-bistributylstannyl-2,2'-binaphtho-20-crown-6 (M-1) with 1,4-dibromo-2,3-bisbutoxy-naphthyl (M-2) by Pd(PPh₃)₄ catalyzed Stille coupling reaction. Both monomer and polymer were analyzed by NMR, MS, FT-IR, UV, polarimetry, DSC-TGA, CD, fluorescent spectroscopy and GPC. The major difference between monomer and polymer is that a long wavelength Cotton Effect was observed for the polymer due to its more extended conjugation in the repeating unit and a highly rigid backbone in the polymer chain. Polymer has strong blue fluorescence due to the efficient energy migration from the extended π-electronic structure of the repeating unit of the polymer to the chiral binaphthyl core and is expected to have potential application in the materials of fluorescent sensors and chiral chromatographic packing for resolution of racemic amino acid.