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Structural and property comparison between the di‐piperidinyl‐ and di‐pyrrolidinyl‐substituted perylene tetracarboxylic diimides
Author(s) -
Feng Junqian,
Wang Delou,
Wang Hailong,
Zhang Daopeng,
Zhang Liangliang,
Li Xiyou
Publication year - 2011
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1799
Subject(s) - chemistry , diimide , perylene , crystal structure , pyrrolidine , piperidine , crystallography , hydrogen bond , stereochemistry , molecule , organic chemistry
Four compounds 1 – 4 connected with cyclic amino groups at the bay positions of perylenetetracarboxylic diimide (PDI) have been prepared and the isomers with 1,7‐ and 1,6‐substituted PDIs were successfully separated by conventional column chromatography. The structures of 1,7‐dipyrrolidinyl‐substituted PDI ( 1 ) and 1,7‐dipiperidinyl‐substituted PDI ( 3 ) were further characterized by single crystal X‐ray diffraction experiments. The crystal structure revealed that the small difference in the molecular structure has caused significant difference on the absorption and emission spectra as well as the electrochemical properties. The shorter bond length of C1N3, together with the more sp2 hybrid atomic orbital characteristics of the nitrogen atom in pyrrolidine relative to those in piperidine is found to be responsible for this large property difference between 1 and 3 . Copyright © 2010 John Wiley & Sons, Ltd.