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Reversible Photogeneration of a Stable Chiral Radical-Pair from a Fast Photochromic Molecule

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Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
Research Institute for Electronic Science, Hokkaido University, N20, W10, Kita-ku, Sapporo 001-0020, Japan
§ Department of Chemistry and Chemical Engineering, Faculty of Engineering, Niigata University, Ikarashi 2-no-cho, Nishi-ku, Niigata 950-2181, Japan
|| Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
CREST, Japan Science and Technology Agency (JST), 5 Sanban-cho, Chiyoda-ku, Tokyo 102-0075, Japan
Cite this: J. Phys. Chem. Lett. 2011, 2, 21, 2680–2682
Publication Date (Web):October 7, 2011
https://doi.org/10.1021/jz2012935
Copyright © 2011 American Chemical Society

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    Abstract

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    The photochromic naphthalene-bridged imidazole dimer containing a naphthyl moiety that tethers two triarylimidazole units shows instantaneous coloration upon exposure to UV light and rapid fading in the dark. In this work, we demonstrate the formation of a stable chiral radical-pair that exhibits no photoracemization even by repeated photochromic cycles. The photogenerated radical-pair from the imidazole dimer exhibits the Cotton effect in the visible light region, indicating the retention of the enantiomeric conformation of the radical-pair. This result suggests that the chirality resulting from the binaphthyl moiety induces exciton coupling between the two radical chromophores by through-space interaction.

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    Details of the measurement of CD spectra and chiral HPLC analyses. This material is available free of charge via the Internet http://pubs.acs.org.

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    2. Tetsuo Yamaguchi, Sayaka Hatano, and Jiro Abe . Multistate Photochromism of 1-Phenylnaphthalene-Bridged Imidazole Dimer That Has Three Colorless Isomers and Two Colored Isomers. The Journal of Physical Chemistry A 2014, 118 (1) , 134-143. https://doi.org/10.1021/jp411190d
    3. Sayaka Hatano, Takeru Horino, Atsuhiro Tokita, Toyoji Oshima, and Jiro Abe . Unusual Negative Photochromism via a Short-Lived Imidazolyl Radical of 1,1′-Binaphthyl-Bridged Imidazole Dimer. Journal of the American Chemical Society 2013, 135 (8) , 3164-3172. https://doi.org/10.1021/ja311344u
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    10. Yoichi Kobayashi, Jiro Abe. Photochromism of Pentaarylbiimidazoles and Phenoxyl-Imidazolyl Radical Complexes. 2017, 153-167. https://doi.org/10.1007/978-4-431-56544-4_7
    11. Kamil Skonieczny, Daniel T. Gryko. Light‐Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π‐Expanded Imidazoles. Chemistry – An Asian Journal 2016, 11 (18) , 2513-2517. https://doi.org/10.1002/asia.201600752
    12. Subramani Swaminathan, Jaume Garcia‐Amorós, Ek Raj Thapaliya, Santi Nonell, Burjor Captain, Françisco M. Raymo. Tuning the Activation Wavelength of Photochromic Oxazines. ChemPhysChem 2016, 17 (12) , 1852-1859. https://doi.org/10.1002/cphc.201600141
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    14. Sameh Helmy, Javier Read de Alaniz. Photochromic and Thermochromic Heterocycles. 2015, 131-177. https://doi.org/10.1016/bs.aihch.2015.05.003
    15. Takahiro Iwasaki, Tetsuya Kato, Yoichi Kobayashi, Jiro Abe. A chiral BINOL-bridged imidazole dimer possessing sub-millisecond fast photochromism. Chem. Commun. 2014, 50 (56) , 7481-7484. https://doi.org/10.1039/C4CC02710H
    16. Hiroaki Yamashita, Jiro Abe. Pentaarylbiimidazole, PABI: an easily synthesized fast photochromic molecule with superior durability. Chem. Commun. 2014, 50 (62) , 8468-8471. https://doi.org/10.1039/C4CC03137G
    17. Takuya Nakashima, Kyohei Yamamoto, Yuka Kimura, Tsuyoshi Kawai. Chiral Photoresponsive Tetrathiazoles That Provide Snapshots of Folding States. Chemistry – A European Journal 2013, 19 (50) , 16972-16980. https://doi.org/10.1002/chem.201302564
    18. Jiro Abe. Fast Photochromism of Bridged Imidazole Dimers. 2013, 161-181. https://doi.org/10.1007/978-4-431-54291-9_9
    19. Sayaka Hatano, Jiro Abe. A peroxide-bridged imidazole dimer formed from a photochromic naphthalene-bridged imidazole dimer. Physical Chemistry Chemical Physics 2012, 14 (16) , 5855. https://doi.org/10.1039/c2cp40239d

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