title: An optically and thermally switchable electronic structure based on an anthracene-BODIPY conjugate.
abstract: An optically and thermally responsive boron dipyrromethene (BODIPY) dye, namely, meso-2-(9,10-dihydro-9,10-ethanoanthracene-11,12-dione) (DK)-linked, bicyclo[2.2.2]octadiene (BCOD)-fused BODIPY (BCOD-DK), was synthesized. The weakly luminous structure of BCOD-DK can be changed quantitatively to that of the strongly fluorescent BODIPY BCOD-Ant by optical excitation at the DK unit, which induces double decarbonylation of the DK unit to give an anthracene unit. The solvent effect on the fluorescence properties of BCOD-DK suggests that the dramatic change in fluorescence intensity is controlled by intramolecular electron transfer from the BODIPY moiety to the meso-DK substituent. BCOD-DK is converted to meso-DK benzene-fused BODIPY (Benzo-DK) by heating at 220 °C with 64-70 nm redshift of absorption and fluorescence peaks without changing the fluorescence quantum yield of ΦF =0.08 in dichloromethane. Benzo-DK can be converted to strongly fluorescent meso-anthracene benzene-fused BODIPY Benzo-Ant by optical excitation. Thus, BCOD-DK can show four different optical performances simply by irradiation and heating, and hence may be applicable for optical data storage and security data encryption.
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan).
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Aotake
authors.forename: Mitsuharu
authors.initials: M
authors.lastname: Suzuki
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Tahara
authors.forename: Daiki
authors.initials: D
authors.lastname: Kuzuhara
authors.forename: Naoki
authors.initials: N
authors.lastname: Aratani
authors.forename: Naoto
authors.initials: N
authors.lastname: Tamai
authors.forename: Hiroko
authors.initials: H
authors.lastname: Yamada
keywords: dyes/pigments; electron transfer; fluorescence; molecular switches; photochemistry