Self-assembled fluorescent hexaazatriphenylenes that act as a light-harvesting antenna.
In this paper we report the self-assembling nature of fluorescent hexaazatriphenylenes (HATs) 6a-d with six alkyl/alkoxy-chain-containing biphenyl groups and their application to light-harvesting antennae. In a nonpolar solvent and the film state, the HAT derivatives form one-dimensional aggregates with an H-type parallel stacking mode, which were analyzed by 1H NMR, UV-vis, and steady-state and time-resolved fluorescence spectroscopy. When HAT derivative 7 with six perylenediimide moieties is incorporated into the one-dimensional aggregates, an efficient energy transfer takes place from the self-assembled HAT moiety as a light-harvesting antenna to the perylenediimide moiety as an energy acceptor. Further, when HAT derivative 8 with six triphenylamino moieties is newly added to the light-harvesting system, an intermolecular electron transfer occurs subsequently between the electron-accepting perylenediimide molecule and the electron-donating triphenylamino molecule.
Ishi-i
Tsutomu
T
Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, 6-1 Kasuga-koh-en, Kasuga 816-8580, Japan. ishi-i@kurume-nct.ac.jp
Murakami
Koh-ichi
K
Imai
Yusuke
Y
Mataka
Shuntaro
S
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D004735:Energy Transfer; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D008027:Light; D045342:Light-Harvesting Protein Complexes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D001372:Aza Compounds; D005456:Fluorescent Dyes; D045342:Light-Harvesting Protein Complexes; D010636:Phenols