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

Autor: Mitsutaka Imoto, Maki Ohashi, Motonori Takeda, Hisaji Taniguchi, Hiroshi Ikeda, Akihiro Tamaki, Kazuhiko Mizuno
Rok vydání: 2010
Předmět:
Zdroj: Tetrahedron Letters. 51:5877-5880
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.08.086
Popis: 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, λ f exciplex = 456 nm ). 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, λ f excimer = 404 nm ). 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.
Databáze: OpenAIRE