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. 2015 Jan 14;137(1):82-5.
doi: 10.1021/ja511320f. Epub 2014 Dec 24.

In-plane aromaticity in cycloparaphenylene dications: a magnetic circular dichroism and theoretical study

Naoyuki Toriumi  1 , Atsuya Muranaka, Eiichi Kayahara, Shigeru Yamago, Masanobu Uchiyama
Affiliations

In-plane aromaticity in cycloparaphenylene dications: a magnetic circular dichroism and theoretical study

Naoyuki Toriumi et al. J Am Chem Soc. .

Abstract

The electronic structures of [8]cycloparaphenylene dication ([8]CPP(2+)) and radical cation ([8]CPP(•+)) 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]CPP(2+) shows in-plane aromaticity with a (4n + 2) π-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]CPP(2+) but also all [n]CPP (n = 5-10) dications and dianions exhibit in-plane aromaticity.

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