A Hexaarylbiimidazole‐Terarylene Hybrid: Visible‐to‐NIR‐II Absorption via Sequential Photochromic Reactions

Author:

Mutoh Katsuya1ORCID,Kobayashi Yoichi2ORCID,Nakashima Takuya1ORCID

Affiliation:

1. Department of Chemistry Graduate School of Science Osaka Metropolitan University 3-3-138 Sugimoto, Sumiyoshi-ku Osaka 558-8585 Japan

2. Department of Applied Chemistry College of Life Sciences Ritsumeikan University 1-1-1 Nojihigashi, Kusatsu Shiga 525-8577 Japan

Abstract

AbstractA synergetic interaction between two or more photochromic chromophores has a potential to achieve advanced photochemical properties beyond conventional photochromic molecules and to realize photochemical control of complex systems using only a single molecule. Herein, we report a hybrid photochromic molecule consisting of hexaarylbiimidazole (HABI) and terarylene that exhibits multi‐state photochromism. The biphotochrome hybrid shows four‐state photochromic reaction involving sequentially proceeding photoreactions. The UV or visible light irradiation to the biphotochrome leads to the C−N bond breaking reaction of the HABI in preference to the ring‐closing reaction of the 6π‐electron system in the terarylene unit, leading to two terarylene radical molecules. The photogenerated terarylene radical further exhibits the 6π‐electrocyclization reaction by UV irradiation. The delocalized π‐radical on the closed‐ring form of the terarylene is efficient to enhance the photosensitivity to the NIR−I and ‐II region. Furthermore, a recombination reaction of radicals between the open‐ and closed‐ring isomers of terarylene affords an unprecedented photochromic dimer as a structural isomer of the initial molecule. This is a consequence of the sequential hybrid photochromic system involving the HABI and terarylene units.

Funder

Japan Society for the Promotion of Science

Tokyo Ohka Foundation for The Promotion of Science and Technology

Iketani Science and Technology Foundation

Publisher

Wiley

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