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Perylene Bisimide and Naphthyl‐Based Molecular Dyads: Hydrogen Bonds Driving Co‐planarization and Anomalous Temperature‐Response Fluorescence
Author(s) -
Shang Congdi,
Wang Gang,
Liu Ke,
Jiang Qingwei,
Liu Fengyi,
Chou PiTai,
Fang Yu
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914070
Subject(s) - perylene , fluorescence , chemical mechanical planarization , photochemistry , hydrogen bond , materials science , hydrogen , optoelectronics , chemistry , molecule , nanotechnology , optics , physics , organic chemistry , layer (electronics)
The origin of the positive temperature effect in fluorescence emission of a newly designed perylene bisimide (PBI) derivative with two naphthyl units containing ortho‐methoxy group (NM) at its bay positions (PBI‐2NM) was elucidated. A key point is the finding of a weak hydrogen bond (<5.0 kcal mol −1 ) between the methoxy group of the NM unit and a nearby hydrogen atom of the PBI core. It is the bonding that drives co‐planarization of the different aromatic units, resulting in delocalization of the π‐electrons of the compound as synthesized, inducing fluorescence quenching via intramolecular charge transfer (ICT). With increasing temperature, the co‐planar structure could be distorted in part, resulting in a decreased degree of ICT, and hence leading to enhanced fluorescence emission. The unique positive temperature effect in emission induced by H‐bond‐driven co‐planarization may pave a new avenue in designing functional molecular systems complementary to conventional methods.