3 years ago

Synthesis and Properties of Naphtho[2,3-e]-1,2-azaphosphorine 2-Oxides: PN-Anthracene Analogues

Synthesis and Properties of Naphtho[2,3-e]-1,2-azaphosphorine 2-Oxides: PN-Anthracene Analogues
Darren W. Johnson, Noah A. Takaesu, Michael M. Haley, Lev N. Zakharov, Eisuke Ohta
We report the expedient synthesis of a series of new “PN-anthracene” derivatives, the naphtho[2,3-e]-1,2-azaphosphorine-2-oxides, which incorporate a variety of 3-aryl substituents. These compounds represent a new class of π-extended PN-heterocycles, featuring strong UV absorption, emission in the visible range, and Stokes shifts up to 10000 cm–1. These molecules show alignment of dipoles, strong dimerization through N–H and P═O hydrogen bond donors/acceptors, and efficient aromatic stacking in the solid state.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00281

DOI: 10.1021/acs.organomet.7b00281

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