TY - JOUR
T1 - Pyrene-Bridged Boron Subphthalocyanine Dimers
T2 - Combination of Planar and Bowl-Shaped π-Conjugated Systems for Creating Uniquely Curved π-Conjugated Systems
AU - Nakano, Shota
AU - Kage, Yuto
AU - Furuta, Hiroyuki
AU - Kobayashi, Nagao
AU - Shimizu, Soji
N1 - Funding Information:
This work was partly supported by Grants-in-Aid for Young Scientists A (No. 26708003) from Japan Society for the Promotion of Science (JSPS), for Scientific Research on Innovative Areas, New Polymeric Materials Based on Element-Blocks (No. 15H00756) and System Figuration: Control of Electron and Structural Dynamism for Innovative Functions (No. 15H01001), from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), and for Bilateral Joint Research Program promoted by JSPS and National Research Foundation (NRF) of South Africa. The authors thank Prof. Takeaki Iwamoto and Prof. Shintaro Ishida of Tohoku University for the X-ray measurements.
Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2016/6/1
Y1 - 2016/6/1
N2 - 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. Pyrene-bridged boron subphthalocyanine (SubPc) dimers were synthesized from a mixed-condensation reaction of tetracyanopyrene and tetrafluorophthalonitrile, and their syn and anti isomers were successfully separated. In addition to the redshift of the Q band absorption, combining the curved π-conjugation of SubPc with the planar π-conjugation of pyrene enabled facile embracement of C60 molecules, owing to the enhanced concave-convex π-π stacking interactions.
AB - 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. Pyrene-bridged boron subphthalocyanine (SubPc) dimers were synthesized from a mixed-condensation reaction of tetracyanopyrene and tetrafluorophthalonitrile, and their syn and anti isomers were successfully separated. In addition to the redshift of the Q band absorption, combining the curved π-conjugation of SubPc with the planar π-conjugation of pyrene enabled facile embracement of C60 molecules, owing to the enhanced concave-convex π-π stacking interactions.
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U2 - 10.1002/chem.201600548
DO - 10.1002/chem.201600548
M3 - Article
AN - SCOPUS:84971344191
SN - 0947-6539
VL - 22
SP - 7706
EP - 7710
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 23
ER -