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Naphtho[2,1-e]-1,2-azaphosphorine-2-oxide Derivatives: Synthesis, Optoelectronic Properties, and Self-Dimerization Phenomena
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submitted on 28.03.2019 and posted on 28.03.2019by Chun-Lin DENG, Jeremy P. Bard, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley
A library of
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.