Synthesis and photochromic properties of quinoxalino[e]-annelated dimethyldihydropyrene with planar chirality |
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Authors: | Tsuyoshi Sawada Takao Kihara Yuya Fujikawa Yu Narazaki |
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Institution: | 1. Department of Applied Chemistry and Biochemistry, Kumamoto University, 2-39-1 Kurokami, Kumamoto 860-8555, Japan;2. Kumamoto Institute for Photo-Electro Organics (Phoenics), 3-11-38 Higashi-mach, Kumamoto 862-0902, Japan |
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Abstract: | 9,10-Diacetyl-2,7-di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene annelated with a quinoxaline unit (q-DM-DHP, 3) was prepared from 5,13-di-tert-butyl-8,16-dimethyl2.2]metacyclophane-1,2,9,10-tetraoxide (2) and o-phenylenediamine in two steps. The photochromic isomers of q-DM-DHP 3, closed form 3a and open form 3b, were separated by reverse-phase HPLC, and their isolated UV–visible spectra were estimated. The chiral HPLC analyses of q-DM-DHP 3 indicated their planar chirality, and their CD spectra were measured. The photochromic properties and thermodynamic properties of 3 were also discussed based on their UV–visible, 1H NMR, CD, and fluorescence spectra. |
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Keywords: | Photochromism Chirality Dihydropyrene Emission Cyclization |
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