Issue 45, 2012
From the journal:

Chemical Communications

Angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran: are they isoelectronic with chrysene?†‡

Masahiro Nakano,§a   Shoji Shinamura,§a   Yoshinobu Houchin,a   Itaru Osaka,a   Eigo Miyazakia  and  Kazuo Takimiya*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan
E-mail: ktakimi@hiroshima-u.ac.jp
Fax: +81-82-424-5494
Tel: +81-82-424-7734

Abstract

Although angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran, are formally isoelectronic with chrysene as their thiophene counterparts, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-dithiophene, the HOMO energy level of naphthodifurans is much higher than those of naphthodithiophenes and chrysene. The difference in electronic structure in the ground state can be explained by distinct electronic perturbation from the outermost aromatic rings.

Graphical abstract: Angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran: are they isoelectronic with chrysene?

  • This article is part of the themed collection: Aromaticity
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Article information

DOI
https://doi.org/10.1039/C2CC31546G
Article type
Communication
Submitted
29 Feb 2012
Accepted
16 Apr 2012
First published
17 Apr 2012

Chem. Commun., 2012,48, 5671-5673

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Angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran: are they isoelectronic with chrysene?

M. Nakano, S. Shinamura, Y. Houchin, I. Osaka, E. Miyazaki and K. Takimiya, Chem. Commun., 2012, 48, 5671 DOI: 10.1039/C2CC31546G

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