Pyrene-Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl-Shaped π-Conjugated Systems for Creating Uniquely Curved π-Conjugated Systems

Shota Nakano; Yuto Kage; Hiroyuki Furuta; Nagao Kobayashi; Soji Shimizu

doi:10.1002/chem.201600548

Pyrene-Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl-Shaped π-Conjugated Systems for Creating Uniquely Curved π-Conjugated Systems

Chemistry. 2016 Jun 1;22(23):7706-10. doi: 10.1002/chem.201600548. Epub 2016 Apr 27.

Authors

Shota Nakano¹, Yuto Kage², Hiroyuki Furuta^{2

3}, Nagao Kobayashi^{4

5}, Soji Shimizu^{6

7}

Affiliations

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan.
² Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.
³ Center for Molecular Systems (CMS), Kyushu University, Fukuoka, 819-0395, Japan.
⁴ Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan. nagaok@shinshu-u.ac.jp.
⁵ Faculty of Textile Science and Technology, Shinshu University, Ueda, 386-8567, Japan. nagaok@shinshu-u.ac.jp.
⁶ Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan. ssoji@cstf.kyushu-u.ac.jp.
⁷ Center for Molecular Systems (CMS), Kyushu University, Fukuoka, 819-0395, Japan. ssoji@cstf.kyushu-u.ac.jp.

PMID: 27120415
DOI: 10.1002/chem.201600548

Abstract

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.

Keywords: UV/Vis spectroscopy; curved π-conjugated system; fullerene; pyrene; subphthalocyanine.

Publication types

Research Support, Non-U.S. Gov't