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Photochromic Terarylenes

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Abstract

Properties of photochromic terarylenes are described as a novel series of photochromic switching molecules. The chemical structure of terarylenes can be recognized as an extension of diarylethenes modified at the central ethene moiety with extended π-conjugated systems. Terarylenes also show photo-induced 6π-electrocyclization reaction in a similar manner to that of diarylethenes. A variety of terarylene structures with various combinations of heteroaromatics could be achieved by metal-catalyzed conventional aryl–aryl cross-coupling methods as well as azole-forming condensation reactions from bis(heteroaryl)-α-hydroxyketones. The conformations of terarylenes are controlled both in solution and crystal with the molecular design of terarylenes by means of the combinations of heteroaromatics including their coupling directions, leading to the design of photo-switching molecules with ultimately high sensitivity. The modification of less versatile ethene moiety of diarylethenes with various π-conjugation systems has expanded the versatility as photo-switching molecular materials. In this chapter, we review the chemistry of photochromic terarylenes including synthetic approaches, photochromic properties, and various photo-switching properties.

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Authors and Affiliations

  1. Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara, 630-0192, Japan

    Takuya Nakashima & Tsuyoshi Kawai

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  1. Takuya Nakashima
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  2. Tsuyoshi Kawai
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Correspondence to Takuya Nakashima .

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Editors and Affiliations

  1. Rikkyo University, Tokyo, Japan

    Masahiro Irie

  2. Yokohama National University, Yokohama, Japan

    Yasushi Yokoyama

  3. Nagoya University, Nagoya, Japan

    Takahiro Seki

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Nakashima, T., Kawai, T. (2013). Photochromic Terarylenes. In: Irie, M., Yokoyama, Y., Seki, T. (eds) New Frontiers in Photochromism. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54291-9_10

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