Naphtho[2,1- e]-1,2-azaphosphorine 2-Oxide Derivatives: Synthesis, Optoelectronic Properties, and Self-Dimerization Phenomena

Chun-Lin Deng; Jeremy P Bard; Lev N Zakharov; Darren W Johnson; Michael M Haley

doi:10.1021/acs.joc.9b00994

Naphtho[2,1- e]-1,2-azaphosphorine 2-Oxide Derivatives: Synthesis, Optoelectronic Properties, and Self-Dimerization Phenomena

J Org Chem. 2019 Jun 21;84(12):8131-8139. doi: 10.1021/acs.joc.9b00994. Epub 2019 Jun 7.

Authors

Chun-Lin Deng¹, Jeremy P Bard¹, Lev N Zakharov², Darren W Johnson¹, Michael M Haley¹

Affiliations

¹ Department of Chemistry & Biochemistry and the Materials Science Institute , University of Oregon , Eugene , Oregon 97403-1253 , United States.
² CAMCOR , University of Oregon , Eugene , Oregon 97403-1433 , United States.

PMID: 31117581
DOI: 10.1021/acs.joc.9b00994

Abstract

A family of naphtho[2,1- e]-fused 1,2-azaphosphorine 2-oxides that contain electron-withdrawing and -donating substituents on the 3-phenyl groups has been prepared and characterized. This new series of phosphorus- and nitrogen-containing heterocycles is brightly fluorescent with tunable emission wavelengths (λ_em = 441-493 nm, Φ_F = 0.19-0.93). Their strong self-dimerization behavior through N-H and P═O hydrogen bond donors/acceptors was investigated experimentally and theoretically. The pendant phenyl group can be used to modify the intrinsic optoelectronic properties as well as the self-association of the PN-heterocycles. The results presented herein are expected to enable the development of new photofunctional materials and provide important insights in diverse areas of supramolecular chemistry.