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Synthesis, Characterization, and Self‐Assembly of Nitrogen‐Containing Heterocoronenetetracarboxylic Acid Diimide Analogues: Photocyclization of N‐Heterocycle‐Substituted Perylene Bisimides
Author(s) -
Li Yongjun,
Li Yuliang,
Li Junbo,
Li Cuihong,
Liu Xiaofeng,
Yuan Mingjian,
Liu Huibiao,
Wang Shu
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600605
Subject(s) - diimide , perylene , stacking , imidazole , self assembly , chemistry , conjugated system , porphyrin , combinatorial chemistry , photochemistry , materials science , polymer chemistry , stereochemistry , organic chemistry , molecule , polymer
Abstract Novel dibenzocoronenetetracarboxylic acid diimide analogues and naphthoperylenetetracarboxylic acid diimide analogues containing imidazole, 1,2,4‐triazole, and pyrazole rings embedded as functional constituents within the parent hydrocarbon backbone have been synthesized. The π‐rich and π‐poor heterocycles have different influences on the physical properties of the parent benzocoronenetetracarboxylic acid diimide and naphthoperylenetetracarboxylic acid diimide systems. The π‐rich 3 was able to self‐assemble into one‐dimensional nanostructures through strong π–π stacking, whereas the π‐poor 8 lacked the one‐dimensional self‐assembly capability, thus offering the potential to control the self‐assembly capability of the π‐conjugated perylene core by decoration with N‐heterocycles.