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2,3:5,6‐bis(ethylenedithio)‐ and bis(trimethylenedithio)‐N,N′‐ dicyanoquinonediimines as new electron acceptors
Author(s) -
Otsubo T.,
Nobuhara Y.,
Kanefuji K.,
Aso Y.,
Ogura F.
Publication year - 1988
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.610010505
Subject(s) - chemistry , substituent , electron acceptor , potassium , metal , copper , derivative (finance) , electron transfer , sodium , crystallography , stereochemistry , photochemistry , organic chemistry , financial economics , economics
In order to examine the substituent effect of ethylenedithio and trimethylenedithio groups on electron acceptors, the two title compounds were prepared in one step from the corresponding quinones. These species behave as weak π‐electron acceptors owing to the electronic and sterical effects of the fused groups. Only the bis(ethylenedithio) derivative formed a charge‐transfer complex with tetrathiotetracene, which showed a moderate electric conductivity of 2·0 × 10 −2 S cm −1 . In addition, both species oxidized copper, sodium, and potassium iodides to give the corresponding deeply colored metal salts, most of which were semiconductive. The naphtho analogs were similarly studied, but hardly served as electron acceptors.