title: Synthesis and Optical Properties of Imidazole- and Benzimidazole-Based Fused π-Conjugated Compounds: Influence of Substituent, Counteranion, and π-Conjugated System.
abstract: Fused π-conjugated imidazolium chlorides having hydrogen (1-Cl), octyloxy (2-Cl), N,N-dibutylamino (3-Cl), trifluoromethyl (4-Cl), and cyano (5-Cl) groups substituted on the benzene ring at the 2-position of imidazole were prepared. Counteranion exchanges from chloride to bis(trifluoromethanesulfonyl)imidate (2-TFSI) and tetrafluoroborate (2-BF4) were performed. The optical properties of these compounds (absorption and emission wavelengths, fluorescence quantum yield, and solvatochromism) were influenced by both the substituent and anion character, which was investigated by theoretical calculations using the density functional theory (DFT) and symmetry-adapted cluster-configuration interaction (SAC-CI) methods. Fused π-conjugated benzimidazolium chlorides having N,N-dibutylamino (6-Cl) and cyano (7-Cl) groups were also prepared to observe the different solvatochromic shifts.
authors.affiliation: †Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa, Nagoya 466-8555 Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Takagi
authors.affiliation: †Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa, Nagoya 466-8555 Japan.
authors.forename: Kazuma
authors.initials: K
authors.lastname: Kusafuka
authors.affiliation: †Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa, Nagoya 466-8555 Japan.
authors.forename: Yohei
authors.initials: Y
authors.lastname: Ito
authors.affiliation: †Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa, Nagoya 466-8555 Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Yamauchi
authors.affiliation: †Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa, Nagoya 466-8555 Japan.
authors.forename: Kaede
authors.initials: K
authors.lastname: Ito
authors.affiliation: ‡Research Center for Computational Science, Institute for Molecular Science, 38 Nishigo-Naka, Myodaiji, Okazaki 444-8585 Japan.|§Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Kyoto 615-8520 Japan.
authors.forename: Ryoichi
authors.initials: R
authors.lastname: Fukuda
authors.affiliation: ‡Research Center for Computational Science, Institute for Molecular Science, 38 Nishigo-Naka, Myodaiji, Okazaki 444-8585 Japan.|§Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Kyoto 615-8520 Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Ehara