An Optically and Thermally Switchable Electronic Structure Based on an Anthracene-BODIPY Conjugate

作者：Aotake Tatsuya; Suzuki Mitsuharu; Tahara Kazuaki; Kuzuhara Daiki; Aratani Naoki; Tamai Naoto; Yamada Hiroko^*

来源：Chemistry - A European Journal, 2015, 21(13): 4966-4974.

DOI：10.1002/chem.201406384

• dyes/pigments
• electron transfer
• fluorescence
• molecular switches
• photochemistry

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 degrees C with 64-70 nm red-shift of absorption and fluorescence peaks without changing the fluorescence quantum yield of Phi(F)=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.

• 出版日期2015-3-23