Merck

An optically and thermally switchable electronic structure based on an anthracene-BODIPY conjugate.

Chemistry (Weinheim an der Bergstrasse, Germany) (2015-02-25)
Tatsuya Aotake, Mitsuharu Suzuki, Kazuaki Tahara, Daiki Kuzuhara, Naoki Aratani, Naoto Tamai, Hiroko Yamada
RESUMO

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.

MATERIAIS
Número do produto
Marca
Descrição do produto

Sigma-Aldrich
Acetonitrile solution, contains 0.1 % (v/v) trifluoroacetic acid, suitable for HPLC
Sigma-Aldrich
Aluminum oxide, mesoporous, MSU-X (wormhole), average pore size 3.8 nm
Supelco
Residual Solvent - Toluene, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
Residual Solvent - Acetonitrile, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Aluminum oxide, nanopowder, <50 nm particle size (TEM)
Sigma-Aldrich
Ultrapure Acetonitrile, for DNA synthesis
Sigma-Aldrich
Acetonitrile, for DNA synthesis
Sigma-Aldrich
Aluminum oxide, nanoparticles, <50 nm particle size (DLS), 20 wt. % in isopropanol
Sigma-Aldrich
Aluminum oxide, nanowires, diam. × L 2-6 nm × 200-400 nm
Sigma-Aldrich
Aluminum oxide, 99.997% trace metals basis
Sigma-Aldrich
Toluene, anhydrous, 99.8%
Sigma-Aldrich
Acetonitrile, anhydrous, 99.8%
Supelco
Aluminum oxide, activated, neutral, Brockmann Activity I
Supelco
Acetonitrile, analytical standard
Supelco
Toluene, analytical standard
Supelco
Aluminum oxide, for the determination of hydrocarbons
Supelco
Toluene, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Aluminum oxide, nanoparticles, 30-60 nm particle size (TEM), 20 wt. % in H2O
Sigma-Aldrich
Aluminum oxide, single crystal substrate, <0001>
Sigma-Aldrich
Acetonitrile, electronic grade, 99.999% trace metals basis
Sigma-Aldrich
Toluene, ACS reagent, ≥99.5%
Sigma-Aldrich
Aluminum oxide, activated, basic, Brockmann I
Sigma-Aldrich
Aluminum oxide, activated, neutral, Brockmann I
Sigma-Aldrich
Acetonitrile, for preparative HPLC, ≥99.8% (GC)
Sigma-Aldrich
Aluminum oxide, Type WN-6, Neutral, Activity Grade Super I
Sigma-Aldrich
Aluminum oxide, powder, primarily α phase, ≤10 μm avg. part. size, 99.5% trace metals basis
Sigma-Aldrich
Aluminum oxide, pore size 58 Å, ~150 mesh
Sigma-Aldrich
Acetonitrile, ACS reagent, ≥99.5%
Sigma-Aldrich
Aluminum oxide, pellets, 3 mm
Sigma-Aldrich
Aluminum oxide, powder, 99.99% trace metals basis