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Issue 35, 2008
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Theoretical study on oligothiophene N-succinimidyl esters: size and push–pull effects

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Abstract

We report a theoretical study on the optical properties of bithiophene and terthiophene N-succinimidyl esters, which have been functionalized with a methylsulfanyl group in the α or the β positions. Time-dependent density functional theory (TD-DFT) and approximate coupled-cluster singles and doubles with the resolution of identity technique (RI-CC2) calculations have been performed in the ground and excited states. The RI-CC2 results for absorption and fluorescence energies are in better qualitative agreement with experiments, whereas TD-DFT does not correctly describe the higher energy part of the absorption spectra of β-substituted bithiophenes, due to the presence of charge-transfer states. Systems functionalized at the α position show a large red-shift of the main absorption and fluorescence band and a larger Stokes-shift compared to the unsubstituted species. These effects are in most cases less pronounced for the β-substituted structures. In particular, we found that the Stokes-shift of the α-substituted structures is larger than the one of the β-substituted species due to a more planar orientation of the methylsulfanyl group with respect to the neighbouring thiophene in the excited state.

Graphical abstract: Theoretical study on oligothiophene N-succinimidyl esters: size and push–pull effects

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Publication details

The article was received on 07 Mar 2008, accepted on 29 May 2008 and first published on 08 Jul 2008


Article type: Paper
DOI: 10.1039/B803963A
Citation: Phys. Chem. Chem. Phys., 2008,10, 5363-5373
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    Theoretical study on oligothiophene N-succinimidyl esters: size and push–pull effects

    M. Piacenza, M. Zambianchi, G. Barbarella, G. Gigli and F. Della Sala, Phys. Chem. Chem. Phys., 2008, 10, 5363
    DOI: 10.1039/B803963A

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