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1,2,3,4,5‐[1′,8′] Anthra‐8,9;10,11‐dibenzo[13]annulene and 1,8‐Distyrylanthracene as Models for Phenylenevinylene Species. Syntheses, Structures, and Redox Properties
Author(s) -
Klabunde KayUwe,
Huber Walter,
Lex Johann,
Müllen Klaus
Publication year - 1987
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.19871200905
Subject(s) - chemistry , annulene , stereochemistry , crystallography , crystal structure
The synthesis of the title compound 4 , formally a [13] perimeter, and of its acyclic model system, 1,8‐distyrylanthracene ( 6 ) is described. The crystal structure of 4 reveals the configuration of the double bonds and the conformation of the macrocycle. Related findings come from the 1 H‐NMR spectroscopic characterization of 4 and 6 in solution. The spin density distribution of the radical anions 4 −· and 6 −· is interpretet in terms of the singly occupied molecular orbital and of the prevailing geometry. In contrast to 4 , compund 6 proves to be an efficient electron acceptor since it can even be reduced to a tetraanion salt. The complete redox sequence is characterized by NMR and ESR spectroscopy.