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Synthesis and Characterization of N,N′‐Substituted 15,15,16,16‐Tetracyano‐6,13‐pentacenequinodimethane‐2,3,9,10‐tetracarboxylic Diimide Derivatives
Author(s) -
Wu Ti,
Chen Jianming,
Guo Yunlong,
Yu Gui,
Shuai Zhigang,
Liu Yunqi
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200119
Subject(s) - diimide , chemistry , electron delocalization , reagent , delocalized electron , homo/lumo , combinatorial chemistry , stereochemistry , organic chemistry , molecule , perylene
How low can you go? N,N′‐substituted 15,15,16,16‐tetracyano‐6,13‐pentacenequinodimethane‐2,3,9,10‐tetracarboxylic diimide derivatives (TCPQDI‐OC8 and TCPQDI‐OC10) were prepared in the presence of Lehnert's reagent at room temperature in good yields from the corresponding quinones. The tetracarboxylic diimide units in TCPQDI derivatives increase the π delocalization and lead to low LUMO energy levels of less than −4.0 eV.