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Synthesis of [all]‐ S , S ‐Dioxide Oligothiophenes Using HOF⋅CH 3 CN
Author(s) -
Amir Elizabeta,
Rozen Shlomo
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200501681
Subject(s) - stacking , acetonitrile , chemistry , solid state , stereochemistry , organic chemistry
Nonaromatic stable polyenes are obtained by dioxygenation of oligothiophenes using HOF⋅CH 3 CN prepared in situ by passing F 2 through aqueous acetonitrile (see scheme). These fully S , S ‐dioxygenated derivatives have a considerably smaller HOMO–LUMO gap than the parent compounds; furthermore, in the solid state they tend to form favorable π–π stacking interactions, unlike most non‐oxidized oligothiophenes which adopt the “herringbone” motif.