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A New Monomer for π‐Conjugated Polymers — Synthesis and Characterization of Bis(( Z )‐5‐phenyl‐2‐phenylmethylidene‐1, 3‐dithiole‐4‐yl)monosulfane
Author(s) -
Schäper Jan,
Hahn Josef,
Pantenburg Ingo,
Scherer Harald
Publication year - 2003
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200390009
Subject(s) - double bond , monomer , chemistry , conjugated system , molecule , proton nmr , proton , stereochemistry , coupling reaction , carbon 13 nmr , crystallography , polymer , polymer chemistry , organic chemistry , catalysis , physics , quantum mechanics
Bis(( Z )‐5‐phenyl‐2‐phenylmethylidene‐1, 3‐dithiole‐4‐yl)monosulfane ( 6 ), a molecule consisting of two diphenyldithiafulvene units connected by a sulfur bridge, was synthesized by the selective lithiation of ( Z )‐4‐phenyl‐2‐phenylmethylidene‐1, 3‐dithiole ( 7a ) at the endocyclic double bond and by subsequent reaction of the lithiated intermediate with bis(phenylsulfonyl)sulfane. Since this reaction sequence proceeded with retention of configuration, of three possible isomers ( E , E , Z , E , and Z , Z ) only the Z , Z form was obtained. On the basis of the X‐ray structure analysis and the NMR‐spectroscopic characterization of 6 supplemented by the NMR parameters of ( E )‐ and ( Z )‐4‐phenyl‐2‐phenylmethylidene‐1, 3‐dithiole, it was demonstrated that two characteristic 5 J coupling constants of the proton at the exocyclic double bond indicate the configuration ( Z or E ) of disubstituted dithiafuvene derivatives.