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Self‐Assembling Aryl‐Naphthalendiimide Derivatives with a Nitroxide Radical
Author(s) -
Nakatsuji Shin'ichi,
Aoki Kazunori,
Kojoh Ayumi,
Akutsu Hiroki,
Yamada Junichi,
Karakawa Makoto,
Aso Yoshio
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.201200095
Subject(s) - chemistry , nitroxide mediated radical polymerization , aryl , radical , aryl radical , stereochemistry , combinatorial chemistry , organic chemistry , polymer , alkyl , radical polymerization , polymerization
Abstract A series of aryl‐substituted naphthalenediimide derivatives that contain nitroxide radicals were prepared and their crystal structures were elucidated. Much stronger charge‐transfer interactions were present in the derivatives with perfluorobenzene substituents than those with phenyl or 4‐fluorophenyl substituents. These interactions result in the formation of single‐component charge‐transfer complexes by self‐assembly of the naphthalenediimide derivatives to provide black crystals. As a consequence, the naphthalenediimide derivatives with perfluorobenzene substituents have better field‐effect transistor (FET) properties than the other derivatives.