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Synthesis, Photophysical Characterization, and Self‐Assembly of Hexa‐ peri ‐hexabenzocoronene/Benzothiadiazole Donor–Acceptor Structure
Author(s) -
Hu Yunbin,
Dössel Lukas F.,
Wang XiaoYe,
Mahesh Sankarapillai,
Pisula Wojciech,
De Feyter Steven,
Feng Xinliang,
Müllen Klaus,
Narita Akimitsu
Publication year - 2017
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201700162
Subject(s) - density functional theory , dihedral angle , molecule , acceptor , crystallography , scanning tunneling microscope , chemistry , materials science , absorption (acoustics) , nanotechnology , computational chemistry , hydrogen bond , organic chemistry , physics , composite material , condensed matter physics
Hexa‐ peri ‐hexabenzocoronene (HBC) substituted by six benzothiadiazole (BTZ) units with ethynylene bridges is synthesized as a new donor–acceptor (D–A) motif. The C≡C bridges significantly reduce the dihedral angles between HBC and BTZ, and thus, lead to a planar molecular conformation as predicted by density functional theory calculations. The optoelectronic properties are investigated by UV/Vis absorption and emission spectroscopies with absorption and emission maxima at 424 and 650 nm, respectively, demonstrating the tunable electronic structures of HBC through the attachment of electron‐withdrawing BTZ units. Two‐dimensional wide‐angle X‐ray scattering analysis shows that the molecules self‐assemble into liquid‐crystalline columns with high stability over a wide temperature range. Scanning tunneling microscopy reveals the formation of ordered bilayers of the D–A molecules with star‐shaped structures.