Synthesis and Spectroscopic Properties of the Elusive 3a,9a-diazaperylenium Dication

Author

Chariklia Sotiriou-Leventis, Missouri University of Science and TechnologyFollow
Abdel-Monem M. Rawashdeh
Woon Su Oh
Nicholas Leventis, Missouri University of Science and TechnologyFollow

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° tilt between the two quinolizinium building blocks. Dication 1 is photoluminescent in fluid solutions of H2O, CH3CN, and CH3NO2, 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.

Recommended Citation

C. Sotiriou-Leventis et al., "Synthesis and Spectroscopic Properties of the Elusive 3a,9a-diazaperylenium Dication," Organic Letters, American Chemical Society (ACS), Oct 2002.

The definitive version is available at https://doi.org/10.1021/ol0268687

Department(s)

Chemistry

Sponsor(s)

National Cancer Institute
Petroleum Research Fund

International Standard Serial Number (ISSN)

1523-7060

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2002 American Chemical Society (ACS), All rights reserved.

Publication Date

01 Oct 2002