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

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...

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Bibliographic Details
Published in:Organometallics 2017-07, Vol.36 (14), p.2491-2493
Main Authors: Takaesu, Noah A, Ohta, Eisuke, Zakharov, Lev N, Johnson, Darren W, Haley, Michael M
Format: Article
Language:English
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Summary: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.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.7b00281