Synthesis, characterization, and self-assembly of nitrogen-containing heterocoronenetetracarboxylic acid diimide analogues: photocyclization of N-heterocycle-substituted perylene bisimides.
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 pi-rich and pi-poor heterocycles have different influences on the physical properties of the parent benzocoronenetetracarboxylic acid diimide and naphthoperylenetetracarboxylic acid diimide systems. The pi-rich 3 was able to self-assemble into one-dimensional nanostructures through strong pi-pi stacking, whereas the pi-poor 8 lacked the one-dimensional self-assembly capability, thus offering the potential to control the self-assembly capability of the pi-conjugated perylene core by decoration with N-heterocycles.
Li
Yongjun
Y
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, P.R. China. ylli@iccas.ac.cn
Li
Yuliang
Y
Li
Junbo
J
Li
Cuihong
C
Liu
Xiaofeng
X
Yuan
Mingjian
M
Liu
Huibiao
H
Wang
Shu
S