Synthesis and spectroscopic properties of the elusive 3a,9a-diazaperylenium dication

Org Lett. 2002 Nov 14;4(23):4113-6. doi: 10.1021/ol0268687.

Abstract

The 3a,9a-diazaperylenium dication (1) was synthesized for the first time in two steps from p-phenylene diamine. Ab initio calculations show a twisted ground state with a 6.4 degrees tilt between the two quinolizinium building blocks. Dication 1 is photoluminescent in fluid solutions of H(2)O, CH(3)CN, and CH(3)NO(2), but not in rigid matrices of the same solvents. This phenomenon has been attributed to a geometric relaxation of the tilted ground state into an emitting planar lowest singlet excited state. [structure: see text]

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Cations, Divalent*
  • Indicators and Reagents
  • Models, Molecular
  • Molecular Conformation
  • Perylene / analogs & derivatives*
  • Perylene / chemical synthesis*

Substances

  • Aza Compounds
  • Cations, Divalent
  • Indicators and Reagents
  • Perylene