Synthesis and spectroscopic properties of the elusive 3a,9a-diazaperylenium dication.
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]
Sotiriou-Leventis
Chariklia
C
Department of Chemistry, University of Missouri-Rolla, Rolla, MO 65409, USA. leventis@umr.edu
Rawashdeh
Abdel-Monem M
AM
Oh
Woon Su
WS
Leventis
Nicholas
N
D001372:Aza Compounds / Q000138:chemical synthesis*; D002413:Cations, Divalent; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D001372:Aza Compounds; D002413:Cations, Divalent; D007202:Indicators and Reagents; D010569:Perylene