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

POLYBINAPHTHYLS INCORPORATING (R)-2,2'-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES
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摘要 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. 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.
出处 《Chinese Journal of Polymer Science》 SCIE CAS CSCD 2006年第6期619-625,共7页 高分子科学(英文版)
基金 This work was supported by the National Natural Science Foundation of China (No. 20474028)Jiangsu Provincial Natural Science Foundation (No. BK2004086).
关键词 (R)-2 2'-Binaphtho-20-crown-6 Chiral polymer Fluorescence Stille reaction. (R)-2,2'-Binaphtho-20-crown-6 Chiral polymer Fluorescence Stille reaction.
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