title: Self-assembled fluorescent hexaazatriphenylenes that act as a light-harvesting antenna.
abstract: 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.
authors.affiliation: Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, 6-1 Kasuga-koh-en, Kasuga 816-8580, Japan. ishi-i@kurume-nct.ac.jp
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Ishi-i
authors.forename: Koh-ichi
authors.initials: K
authors.lastname: Murakami
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Imai
authors.forename: Shuntaro
authors.initials: S
authors.lastname: Mataka
mesh_terms: 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
chemical_list: D001372:Aza Compounds; D005456:Fluorescent Dyes; D045342:Light-Harvesting Protein Complexes; D010636:Phenols