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

Dan Zhu; Yi-xiang Cheng; Xiao-wei Zou; Ling-wu Chen; Jin-feng Song and Zhi-liu Wang College of Chemistry and Chemical Engineering; Nanjing University; Nanjing 210093; China

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

Updated：2021-06-21

- POLYBINAPHTHYLS INCORPORATING （R）-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES
- POLYBINAPHTHYLS INCORPORATING （R）-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES
- 高分子科学（英文版） 2006年第6期页码：619-625
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  This work was supported by the National Natural Science Foundation of China （No. 20474028）Jiangsu Provincial Natural Science Foundation （No. BK2004086）.()
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Dan Zhu, Yi-xiang Cheng, Xiao-wei Zou, 等. POLYBINAPHTHYLS INCORPORATING （R）-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES[J]. 高分子科学（英文版）, 2006,(6):619-625.

Dan Zhu, Yi-xiang Cheng, Xiao-wei Zou, et al. POLYBINAPHTHYLS INCORPORATING （R）-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES[J]. 2006,(6):619-625.
Dan Zhu, Yi-xiang Cheng, Xiao-wei Zou, 等. POLYBINAPHTHYLS INCORPORATING （R）-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES[J]. 高分子科学（英文版）, 2006,(6):619-625. DOI：

Dan Zhu, Yi-xiang Cheng, Xiao-wei Zou, et al. POLYBINAPHTHYLS INCORPORATING （R）-2,2’-BINAPHTHO-20-CROWN-6 AND NAPHTHYL MOITIES[J]. 2006,(6):619-625. DOI：

摘要

<正>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 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 of racemic amino acid.

Abstract

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 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 of racemic amino acid.

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