In-Plane Aromaticity in Cycloparaphenylene Dications: A Magnetic Circular Dichroism and Theoretical Study

被引：110

作者：

Toriumi, Naoyuki ^{[1
]}

Muranaka, Atsuya ^{[2
,3
]}

Kayahara, Eiichi ^{[4
,5
]}

Yamago, Shigeru ^{[4
,5
]}

Uchiyama, Masanobu ^{[1
,2
,3
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

[2] RIKEN, Elements Chem Lab, Wako, Saitama 3510198, Japan

[3] RIKEN, Adv Elements Chem Res Team, CSRS, Wako, Saitama 3510198, Japan

[4] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan

[5] Japan Sci & Technol Agcy, CREST, Tokyo 1020076, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 01期

基金：

日本科学技术振兴机构;

关键词：

DENSITY-FUNCTIONAL THEORY; SELECTIVE SYNTHESIS; RADICAL-CATION; EMERALD GREEN; MOLECULES; DEPENDENCE; ZN; NI;

D O I：

10.1021/ja511320f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The electronic structures of [8]cycloparaphenylene dication ([8]CPP2+) and radical cation ([8]CPP center dot+) have been investigated by magnetic circular dichroism (MCD) spectroscopy, which enabled unambiguous discrimination between previously conflicting assignments of the UV-vis-NIR absorption spectral bands. Molecular orbital and nucleus-independent chemical shift (NICS) analysis revealed that [8]CPP2+ shows in-plane aromaticity with a (4n + 2) pi-electron system (n = 7). This aromaticity appears to be the origin of the unusual stability of the dication. Theoretical calculations further suggested that not only [8]CPP2+ but also all [n]CPP (n = 5-10) dications and dianions exhibit in-plane aromaticity.

引用

页码：82 / 85

页数：4

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