1,2,3-Tri(9-anthryl)benzene: Photophysical Properties and Solid-State Intermolecular Interactions of Radially Arranged,Congested Aromatic π-Planes** |
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Authors: | Dr Tomohiko Nishiuchi Dr Hikaru Sotome Kazuto Shimizu Prof?Dr Hiroshi Miyasaka Prof?Dr Takashi Kubo |
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Institution: | 1. Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043 Japan;2. Division of Frontier Materials Science and Center for, Advanced Interdisciplinary Research, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka, 560-8531 Japan |
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Abstract: | We report the Negishi coupling based synthesis of 1,2,3-tri(9-anthryl)benzene derivatives containing three radially arranged anthracenes in a π-cluster. In the crystalline state of the unsubstituted derivative, intermolecular π–π and CH–π interactions between the anthracene units drive the formation of the two-dimensional packing structure. Owing to though-space π-conjugation between anthracene units, the substances have unique electronic properties. The excited-state dynamic behavior occurring between the three anthracene moieties, such as exciton localization/delocalization, was elucidated by means of transient absorption measurements and quantum chemical calculations. Interestingly, even though the three anthracenes are closely oriented with approximately 3.0 Å between their C-9 positions, exciton localization on two anthracene units is energetically favorable because of the flexible nature of the radially arranged aromatic rings. |
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Keywords: | pi-clusters anthracene CH?pi interactions excited-state dynamics photoisomerization |
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