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Control of the CT interaction between electron-donor and -acceptor moieties of a 1,4-dicyanonaphthalene-arene dyad for intermolecular exciplex or excimer formation in crystals
Authors:Mitsutaka Imoto  Hiroshi Ikeda  Maki Ohashi  Akihiro Tamaki  Kazuhiko Mizuno
Affiliation:a Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
b Seika Corporation, 1-1-82 Kozaika, Wakayama 641-0007, Japan
c The Research Institute for Molecular Electronic Devices (RIMED), Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
Abstract:
Colorless crystals of 1,4-dicyano-2-(4′-methoxybenzyloxy)methylnaphthalene (2), which is a 1,4-dicyano-2-methylnaphthalene (DCMN)-4-methylanisole (MA) dyad linked by an ether unit, selectively form a fluorescent intermolecular DCMN-MA exciplex (greenish blue, View the MathML source). In contrast, 1,4-dicyano-2-(4′-methylbenzyloxy)methylnaphthalene (3), which is a DCMN-p-xylene dyad, forms a fluorescent intermolecular DCMN-DCMN excimer in the crystalline state (blue, View the MathML source). These findings demonstrate that a moderate charge transfer interaction takes place between the DCMN moiety of 2 and MA moieties of the adjacent molecules of 2, which successfully facilitates the preparation of light-emissive organic crystals.
Keywords:Charge transfer   CT complex   Fluorescence   Light-emissive organic crystals   Crystal architecture
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