The first stable tetraarylacenaphthenequinodimethanes exhibiting electrochromism with ‘write-protect’ option: preparation, highly deformed structure, and reversible interconversion with acenaphthylene-5,6-diyl dicationic dyes |
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Authors: | Takanori Suzuki Shinichi Iwashita Hidetoshi Kawai Masakazu Ohkita Kazunori Ono |
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Affiliation: | a Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan b Graduate School of Engineering, Nagoya Institute of Technology, Nagoya 466-8555, Japan c Asahi Kasei Electronic Co., Shioya, Hichiya, Hyuga 883-0062, Japan |
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Abstract: | Severely deformed title quinodimethanes [1,2-bis(diarylmethylene)acenaphthenes] 1 have been designed and prepared as novel electrochromic materials, which can be reversibly interconverted with the deeply colored dicationic dyes 12+ with acenaphthylene-1,2-diyl skeleton. The X-ray analysis of 1 revealed that the inner two aryl groups are forced to overlap in proximity, which can account for the facile electrocyclization process to the isomer. By combination of reversible electrochemical transformation with irreversible isomerization process, the present system provides a prototype for novel molecular response systems equipped with the ‘write-protect’ option. |
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Keywords: | Quinodimethane Strained molecule Steric hindrance Redox system Electrochromism Dye Dication Acenaphthene Electrocyclization |
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