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Solid-state one-way photoisomerisation of Z,E,Z-1,6-(4,4′-diphenyl)hexa-1,3,5-triene dicarboxylate examined using higher-order derivative spectra and powder XRD patterns

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Abstract

Higher order derivative spectra were applied at first to one-way ZEZ-to-EEE photoisomerisation of dimethyl ester (ZEZ-DPH1) of the titled compound in a methylcyclohexane solution. Many common crossing points emerged in UV-induced derivative-spectral changes to reveal the direct ZEZ-to-EEE photoisomerisation without the transient formation of an intermediate to suggest the bicycle-pedal mechanism. The solid-state photoisomerisation was subsequently monitored by tracing changes in the fourth-order derivatives of absorption spectra of a thin crystalline layer of ZEZ-DPH1 prepared by the drop-casting method, because the distortion of absorption spectra due to light scattering is cancelled. It was suggested that the solid-state photochemical event consists of three steps: fast ZEZ-to-EEE photo-isomerisation, a subsequent slow ZEZ-to-EEE photoisomerisation and very slow disappearance of the EEE-isomer. Studies on powder XRD were also carried out for a drop-cast solid layer of ZEZ-DPH1 to disclose the coexistence of a crystal form other than the original one, and the former exhibited faster ZEZ-to- EEE photoisomerisation when compared with the original crystal form. The results revealed by XRD analysis are in line with those obtained by higher-order derivative spectra, confirming the solid-state oneway photoisomerisation to take place through the bicycle-pedal process.

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Authors and Affiliations

  1. Electronics and Photonics Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Higashi 1-1-1, Tsukuba, Ibaraki, 305-8565, Japan

    Yoriko Sonoda

  2. IBEC Center, TIA, AIST, Umezono 1-1-1, Tsukuba, Ibaraki, 305-8568, Japan

    Midori Goto

  3. R & D Centre, Murakami Co. Ltd., 1-6-12 Ohnodai, Midori-ku, Chiba, 267-0056, Japan

    Kunihiro Ichimura

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  1. Yoriko Sonoda
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Correspondence to Kunihiro Ichimura.

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Sonoda, Y., Goto, M. & Ichimura, K. Solid-state one-way photoisomerisation of Z,E,Z-1,6-(4,4′-diphenyl)hexa-1,3,5-triene dicarboxylate examined using higher-order derivative spectra and powder XRD patterns. Photochem Photobiol Sci 17, 271–280 (2018). https://doi.org/10.1039/c7pp00247e

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