Design and synthesis of 2-(1,3-dialkoxy-2-methylpropan-2-yl)-1,3-diarylpropanes as tethering units for folded H-stacking polymers |
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Authors: | Ryota Moriai Yu-suke Naito Ryosuke Nomura Shigeaki Funyu Ken-ich Ishitsuka Naoki Asano Sentaro Okamoto |
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Institution: | 1. Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan;2. Tsukuba Research Laboratory, Hitachi Chemical Co., Ltd, 48 Wadai, Tsukuba-shi, Ibaraki 300-4247, Japan |
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Abstract: | 1,3-Diarylpropenes 9 having a 1,3-dialkoxy-2-methylpropan-2-yl group were designed as tethering monomers for folded H-stacking polymers, and were readily synthesized from 2-ethoxymethylidene malonate in four- or five-steps, including a facile sequential addition–elimination–addition reaction of benzyl zinc reagents. The preference for the closed (stacked) conformation in the resulting 2-substituted 1,3-diarylpropanes 9 was evaluated using MM2 calculations, 1H NMR analyses, and fluorescence measurements. Copolymerization of the resulting monomers 9 with compounds containing π-units provided polymers with blue-shifted UV-absorptions both in solution and as films, compared with that of a model compound containing a single π-unit. This optical property is unique to H-aggregated π-units. |
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Keywords: | Conformation analysis H-Stacking Folded polymers Fluorescence |
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