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Photocontrol of New Molecular Functions by the Isomerization of Azobenzene

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New Frontiers in Photochromism

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Abstract

Azobenzene shows the reversible E–Z photoisomerization upon near ultraviolet (UV) and blue light irradiations. By utilizing changes in the molecular length and polarity of azobenzene in this isomerization, azobenzene has been applied as the molecular switching unit of various molecular functional materials. In this chapter some recent challenges on the photoswitching of new molecular functions using azobenzene derivatives were described. They include the molecular chirality and molecular machines. The feature of these molecular functions is that the control is not accomplished until fine tuning of inter- or intramolecular motions. The racemization of the planar chiral macrocycles 2 and 5 is photochemically and dynamically controlled for the first time by controlling intramolecular free rotation of an asymmetric rotor unit by photoisomerization of an azobenzene moiety in macrocycles. Under circular polarized lights it was possible to enrich one of the enantiomers of 5 as the results of different efficiency of the photoisomerization between racemizing Z isomer and the nonracemizing E enantiomers. It was also demonstrated that point chirality was dynamically introduced by the E–Z photoisomerization of one of the azobenzenes in the methane derivatives substituted with two identical azobenzenes. In the study of molecular machine the sliding motion of a motor protein, kinesin-microtubule, can be controlled by the photoisomerization of azobenzene unit introduced to a monomolecular layer underneath the kinesin or in the adenosine triphosphate (ATP) served as an energy source.

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  1. Research Institute for Electronic Science, Hokkaido University, N20, W10, Kita-ku, Sapporo, 001-0020, Japan

    Nobuyuki Tamaoki

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  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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Tamaoki, N. (2013). Photocontrol of New Molecular Functions by the Isomerization of Azobenzene. In: Irie, M., Yokoyama, Y., Seki, T. (eds) New Frontiers in Photochromism. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54291-9_14

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