Electron-Rich Hexasubstituted Benzene Derivatives and Their Oxidized Cation Radicals, Dications with Potential Triplet Ground States, and Polycations

John Thomaides, Przemyslaw Maslak, Ronald Breslow

Research output: Contribution to journalArticle

54 Scopus citations

Abstract

Five new benzene derivatives have been synthesized carrying electron-releasing substituents. The derivative of hexaaminobenzene with six ethano bridges connecting all the nitrogens can be reversibly oxidized all the way to a tetracation; the dication is a (ground-state) triplet species. Two derivatives of l, 3, 5-trihydroxy-2, 4, 6-triaminobenzene were also prepared, as well as two derivatives of 1, 3, 5-triaminobenzene-2, 4, 6-trithiol. In these cases three ethano bridges connected heteroatoms. Cation radicals could be prepared in all cases, and with one of the oxygen compounds a triplet-state dication was also prepared. The synthetic procedures involved an unusual “zipper” cyclization in the hexaaza series.

Original languageEnglish (US)
Pages (from-to)3970-3979
Number of pages10
JournalJournal of the American Chemical Society
Volume110
Issue number12
DOIs
StatePublished - Jan 1 1988

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Electron-Rich Hexasubstituted Benzene Derivatives and Their Oxidized Cation Radicals, Dications with Potential Triplet Ground States, and Polycations'. Together they form a unique fingerprint.

  • Cite this