Abstract
Although diarylethene derivatives are considered to undergo thermally irreversible photochromic reactions, this is not always the case. Here, we report on thermally reversible photochromic diarylethenes having pyrrole-2-carbonitrile aryl groups. The thermal stability of the coloured closed-ring isomer of 1,2-bis(2-alkyl-5-cyano-1-methyl-3-pyrrolyl)perfluorocyclopentene was found to depend on alkyl substituents at the 2- and 2’-positions. The closed-ring isomer of the ethyl-substituted derivative thermally returned back to the open-ring isomer much faster than that of the methyl-substituted derivative. The difference in the thermal stability was well explained by the ground state energy difference between open- and closed-ring isomers. Excellent fatigue resistance and appropriate thermal fading rates were observed for the derivative having cyano substituents at the 5- and 5’-positions and methyl substituents at the 2-, 2’-, 4- and 4’-positions. The UV-irradiated colouration and thermal decolouration cycle can be repeated more than 103 times.
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Part of the special issue dedicated to the memory of the late Prof. Ugo Mazzucato.
Electronic supplementary information (ESI) available: Syntheses of dipyrrolylethenes 2a–4a and conformations of the closed-ring isomers 1b and 2b. See DOI: 10.1039/c8pp00557e
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Inaba, K., Iwai, R., Morimoto, M. et al. Thermally reversible photochromism of dipyrrolylethenes. Photochem Photobiol Sci 18, 2136–2141 (2019). https://doi.org/10.1039/c8pp00557e
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DOI: https://doi.org/10.1039/c8pp00557e