The doubly oxidized, antiaromatic tetraphenylporphyrin complex [Li(TPP)][BF4]

被引：56

作者：

Cissell, JA

Vaid, TP ^{[1
]}

Yap, GPA

机构：

[1] Washington Univ, Ctr Mat Innovat, St Louis, MO 63130 USA

[2] Washington Univ, Dept Chem, St Louis, MO 63130 USA

[3] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 11期

关键词：

D O I：

10.1021/ol060772l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[graphics] Oxidation of dilithium tetraphenylporphyrin, Li-2(TPP), yields the doubly oxidized porphyrin complex [Li(TPP)][BF4]. Free TPP appears to be unstable. The crystal structure of [Li(TPP)][BF4] reveals that the 16- atom C-N inner ring of the porphyrin consists of alternating single and double bonds. NMR spectroscopy and nucleus-independent chemical shift (NICS) calculations, in addition to the distortion from planarity observed in the crystal structure, indicate that the 16 pi-electron inner C-N ring of the porphyrin is antiaromatic.

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页码：2401 / 2404

页数：4

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