Pyrene-Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl-Shaped π-Conjugated Systems for Creating Uniquely Curved π-Conjugated Systems.
Pyrene-bridged boron subphthalocyanine dimers were synthesized from a mixed-condensation reaction of 2,7-di-tert-butyl-4,5,9,10-tetracyanopyrene and tetrafluorophthalonitrile, and their syn and anti isomers arising from the result of connecting two bowl-shaped boron subphthalocyanine molecules were successfully separated. Expansion of the conjugated system of boron subphthalocyanine through a pyrene bridge caused a redshift of the Q band absorption relative to the parent pyrene-fused monomer, whereas combining the curved π-conjugation of boron subphthalocyanine with the planar π-conjugation of pyrene enabled facile embracement of C60 molecules, owing to the enhanced concave-convex π-π stacking interactions.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan.
Shota
S
Nakano
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.
Yuto
Y
Kage
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.|Center for Molecular Systems (CMS), Kyushu University, Fukuoka, 819-0395, Japan.
Hiroyuki
H
Furuta
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan. nagaok@shinshu-u.ac.jp.|Faculty of Textile Science and Technology, Shinshu University, Ueda, 386-8567, Japan. nagaok@shinshu-u.ac.jp.
Nagao
N
Kobayashi
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan. ssoji@cstf.kyushu-u.ac.jp.|Center for Molecular Systems (CMS), Kyushu University, Fukuoka, 819-0395, Japan. ssoji@cstf.kyushu-u.ac.jp.
Soji
0000-0002-2184-7468
S
Shimizu
UV/Vis spectroscopy; curved π-conjugated system; fullerene; pyrene; subphthalocyanine