Synthesis 1997; 1997(9): 1085-1090
DOI: 10.1055/s-1997-1316
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Tetracyano-4,7-indanoquinodimethanes: The First TCNQs with an Indan Nucleus

Charles A. Panetta*
  • *The Department of Chemistry, The University of Mississippi, University, MS 38677, USA, Fax +1(601)2327300
Further Information

Publication History

Publication Date:
31 December 2000 (online)

8,8,9,9-Tetracyano-4,7-indanoquinodimethane and 5-chloro-8,8,9,9-tetracyano-4,7-indanoquinodimethane, the first members of the hitherto unreported family of tetracyanoindanoquinodimethanes, have been synthesized from the corresponding 4,7-indandicarboxylic acids by the method of Yamaguchi. The indan-TCNQs are part of a series of polycyclic TCNQs which include 11,11,12,12-tetracyano-9,10-anthraquinodimethane and 9,9,10,10-tetracyano-1,4-naphthoquinodimethane, that have been prepared in our laboratory. A disadvantage found with the earlier polycyclic TCNQs was to non-coplanarity of their rings and the dicyanomethylene moities: a planar system is essential to efficient electrical conductivity of TCNQs in CT salts. X-ray analysis has shown 8,8,9,9-tetracyano-4,7-indanoquinodimethane to be more planar compared with tetracyanoanthraquinodimethanes and tetracyanonaphthoquinodimethanes. The half-wave potentials of the chlorotetracyanoindanoquinodimethane show it to be a stronger electron acceptor than several known TCNQs and its cyclic voltammogram indicate two single electron reversible redox processes.