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

preprint
submitted on 28.03.2019 and posted on 28.03.2019 by Chun-Lin DENG, Jeremy P. Bard, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley
A library of novel naphtho[2,1-e]-fused 1,2-azaphosphorine-2-oxides that contain electron-withdrawing and -donating substituents on the 3-phenyl groups have been designed, prepared and characterized. This new family of phosphorus- and nitrogen-containing heterocycles are found to be brightly fluorescent with tuneable emission wavelengths (lem = 441−493nm, FF = 0.19−0.93). Their strong self-dimerization behaviours through N−H and P=O hydrogen bond donors/acceptors were investigated experimentally and theoretically. It has been demonstrated that the pendant phenyl groups can be used to modify the intrinsic optoelectronic properties as well as the self-association of heterocycles. These results presented herein are expected to enable the development of new photofunctional materials and provide important insights in diverse areas of supramolecular chemistry.

History

Email Address of Submitting Author

cldeng@uoregon.edu

Institution

University of Oregon

Country

USA

ORCID For Submitting Author

0000-0002-3192-9424

Declaration of Conflict of Interest

No

Exports