Synthesis, cyclic voltammetric studies, and electrogenerated chemiluminescence of a new phenylquinoline-biphenothiazine donor-acceptor molecule

Rebecca Y. Lai, Xiangxing Kong, Samson A. Jenekhe, Allen J. Bard

Research output: Contribution to journalArticlepeer-review

167 Scopus citations

Abstract

We report the synthesis, electrochemistry, and luminescence of a novel ECL emitting compound containing two electron-accepting hexyl-phenylquinoline groups covalently attached to the 3,3′-positions of the electron-donating 10,10′-dimethylbiphenothiazine group. The optimized geometry as determined from semiempirical MNDO calculations shows that the two quinoline groups are twisted 82.5° from the two phenothiazine rings, indicating a lack of electron delocalization among these groups. This unique geometry allows generation of localized radical cations and radical anions capable of generating ECL upon annihilation. However, the phenothiazine rings are twisted 46.5° relative to each other, suggesting possible interactions between the two moieties. This is evident in the electrochemical behavior in which two closely spaced one-electron oxidations, rather than a single two-electron oxidation wave, were observed. The photophysical properties of BHQ-BPZ show strong resemblances to the parent compound, BPQ-PTZ, which contains a single phenothiazine moiety. In addition, the ECL spectrum produced via radical ion annihilation shows good agreement with the fluorescence emission of the compound.

Original languageEnglish (US)
Pages (from-to)12631-12639
Number of pages9
JournalJournal of the American Chemical Society
Volume125
Issue number41
DOIs
StatePublished - Oct 15 2003

ASJC Scopus subject areas

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

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