Issue 45, 2012

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

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

Supplementary files

Article information

Article type
Communication
Submitted
29 Yan 2012
Accepted
16 Dzi 2012
First published
17 Dzi 2012

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

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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