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Proaromaticity: organic charge-transfer chromophores with small HOMO-LUMO gaps

Wu, Y-L, Bures, F, Jarowski, PD, Schweizer, WB, Boudon, C, Gisselbrecht, J-P and Diederich, FCC (2010) Proaromaticity: organic charge-transfer chromophores with small HOMO-LUMO gaps Chemistry, 16, 31. pp. 9592-605.

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Novel donor- and/or acceptor-substituted cross-conjugated carbocycles based on quinoids or expanded quinoids, with radiaannulene perimeters, were prepared and investigated to validate proaromaticity as a concept for reducing HOMO-LUMO gaps in push-pull chromophores. Analyses of IR, (1)H NMR, and UV/Vis/NIR spectra in conjunction with molecular structures determined by X-ray diffraction show that these push-pull quinoids have significant charge-separated ground states. This feature results in small optical gaps (near IR region) and diatropic magnetic environments inside the carbocycles, as suggested by nucleus-independent chemical shift (NICS) calculations. The NICS results, together with the bond-length analysis of the quinoid spacers, provide strong support that proaromaticity, that is, aromatized zwitterionic mesomeric contributions in the ground state, is effective. A push-pull tetrakis(ethynediyl)-expanded quinoid chromophore represents the first proaromatic radiaannulene.

Item Type: Article
Divisions : Surrey research (other units)
Authors :
Wu, Y-L
Bures, F
Schweizer, WB
Boudon, C
Gisselbrecht, J-P
Diederich, FCC
Date : August 2010
DOI : 10.1002/chem.201001051
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 17 May 2017 11:49
Last Modified : 24 Jan 2020 21:18

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