Work

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

Year: 2019

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.9b00994

Authors: Chun-Lin Deng, Jeremy P. Bard, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley

Institution: University of Oregon

Language: English

Topic: Luminescence and Fluorescent Materials

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Oregon State University, Division of Chemistry

Award: G4422329620