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

被引:14
|
作者
Takaesu, Noah A. [1 ,2 ]
Ohta, Eisuke [1 ,2 ,4 ]
Zakharov, Lev N. [3 ]
Johnson, Darren W. [1 ,2 ]
Haley, Michael M. [1 ,2 ]
机构
[1] Univ Oregon, Dept Chem & Biochem, Eugene, OR 97403 USA
[2] Univ Oregon, Inst Mat Sci, Eugene, OR 97403 USA
[3] Univ Oregon, CAMCOR, Eugene, OR 97403 USA
[4] Osaka Prefecture Univ, Dept Appl Chem, Grad Sch Engn, Naka Ku, 1-1 Gakuen Cho, Sakai, Osaka 5998531, Japan
基金
美国国家科学基金会;
关键词
HETEROCYCLIC PHOSPHORUS-COMPOUNDS; STEREOCHEMISTRY; CYCLIZATION;
D O I
10.1021/acs.organomet.7b00281
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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 pi-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.
引用
收藏
页码:2491 / 2493
页数:3
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