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Synthesis of new soluble triphenodithiazines and investigation of their donor properties
Author(s) -
Kistenmacher Axel,
Adam Martin,
Baumgarten Martin,
Pawlik Jürgen,
Räder HansJoachim,
Müllen Klaus
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250627
Subject(s) - chemistry , electron paramagnetic resonance , benzoquinone , solid state , photochemistry , crystallography , stereochemistry , computational chemistry , organic chemistry , nuclear magnetic resonance , physics
The syntheses of 6 and 7 , starting from 3,6‐dichloro‐2,5‐bis(2‐thioanisido)‐1,4‐benzoquinone ( 4 ), are reported. The solid‐state conformations of 6 and 7 are elucidated by X‐ray structure analysis, and the cyclovoltammetric investigation of 6 and 7 in solution shows low and reversible oxidation half‐waves for both compounds. The relatively high oxidation potentials of 7 compared to 6 are related to their conformational features. EPR measurements on the radical cations derived from 6 and 7 both suggest a planarized conformation of these species. Oxidation of 6 with strong oxidants leads quantitatively to the quinoid triphenodithiazine 8 , whereas the charge‐transfer complex formed between 7 and DDQ exhibits semiconducting properties.