title: Tetraalkoxyphenanthrene-Fused Thiadiazoloquinoxalines: Synthesis, Electronic, Optical, and Electrochemical Properties, and Self-Assembly.
abstract: π-Extended thiadiazoloquinoxaline (TQ) derivatives 1a,b-3a,b, in which a tetraalkoxyphenanthrene moiety is annulated with the TQ core and benzene rings are incorporated via the ethynylene spacer, were synthesized. They display absorption bands reaching into 750 nm and possess the electron-affinity comparable to [60]fullerene. The CF3- and OMe-substituents on the benzene rings have moderate effects on modulation of the HOMO and LUMO levels. Tetraalkoxyphenanthrene-fused TQs 1a,b-3a,b aggregate in the solid state and assemble in solution through π-π stacking interactions. The self-assembly of 1a,b-3a,b into 1D superstructures was confirmed, and the difference in the alkoxy groups and the solvents for self-assembly proved to change their morphology. Comparison of the properties of 1a and those of reference compounds 4 and 5 clarified the effects of both the fusion of the phenanthrene moiety and the introduction of ethynylene spacers on the properties.
authors.affiliation: Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
authors.forename: Shin-Ichiro
authors.initials: SI
authors.lastname: Kato
authors.affiliation: Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
authors.forename: Keitaro
authors.initials: K
authors.lastname: Watanabe
authors.affiliation: Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
authors.forename: Misaki
authors.initials: M
authors.lastname: Tamura
authors.affiliation: Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
authors.forename: Masahiko
authors.initials: M
authors.lastname: Ueno
authors.affiliation: The Institute of Scientific and Industrial Research (ISIR), Osaka University , 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Nitani
authors.affiliation: The Institute of Scientific and Industrial Research (ISIR), Osaka University , 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Ie
authors.affiliation: The Institute of Scientific and Industrial Research (ISIR), Osaka University , 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Aso
authors.affiliation: Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamanobe
authors.affiliation: Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Uehara
authors.affiliation: Division of Molecular Science, Faculty of Science and Technology, Gunma University , 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan.
authors.forename: Yosuke
authors.identifier: 0000-0002-6047-1336
authors.initials: Y
authors.lastname: Nakamura