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Tedesco E, Della F, Favaretto L, et al. Solid-state supramolecular organization, established directly from powder diffraction data, and photoluminescence efficiency of rigid-core oligothiophene-S,S-dioxides. J Am Chem Soc. 2003;125(40):12277-83doi: 10.1021/ja035570o.
Tedesco, E., Della, F., Favaretto, L., Barbarella, G., Albesa-Jové, D., Pisignano, D., Gigli, G., Cingolani, R., & Harris, K. D. (2003). Solid-state supramolecular organization, established directly from powder diffraction data, and photoluminescence efficiency of rigid-core oligothiophene-S,S-dioxides. Journal of the American Chemical Society, 125(40), 12277-83. https://doi.org/10.1021/ja035570o
Tedesco, Emilio, et al. "Solid-state supramolecular organization, established directly from powder diffraction data, and photoluminescence efficiency of rigid-core oligothiophene-S,S-dioxides." Journal of the American Chemical Society vol. 125,40 (2003): 12277-83. doi: https://doi.org/10.1021/ja035570o
Tedesco E, Della F, Favaretto L, Barbarella G, Albesa-Jové D, Pisignano D, Gigli G, Cingolani R, Harris KD. Solid-state supramolecular organization, established directly from powder diffraction data, and photoluminescence efficiency of rigid-core oligothiophene-S,S-dioxides. J Am Chem Soc. 2003 Oct 08;125(40):12277-83. doi: 10.1021/ja035570o. PMID: 14519013.
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J Am Chem Soc. 2003 Oct 08;125(40):12277-83. doi: 10.1021/ja035570o.

Solid-state supramolecular organization, established directly from powder diffraction data, and photoluminescence efficiency of rigid-core oligothiophene-S,S-dioxides.

Journal of the American Chemical Society

Emilio Tedesco, Fabio Della, Laura Favaretto, Giovanna Barbarella, David Albesa-Jové, Dario Pisignano, Giuseppe Gigli, Roberto Cingolani, Kenneth D M Harris

Affiliations

  1. School of Chemical Sciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, United Kingdom.

PMID: 14519013 DOI: 10.1021/ja035570o

Abstract

The "rigid-core" material 3,5-dimethyl-2,3'-bis(3-methylthiophene)-dithieno[3,2-b:',3'-d]thiophene-4,4-dioxide (DTTOMe4) has the highest photoluminescence ever reported for thiophene-based molecules in the solid state. We report the structure of this material, determined directly from powder X-ray diffraction data using the Genetic Algorithm method for structure solution, followed by Rietveld refinement, and the structural properties are discussed in relation to the structures of the corresponding subsystems DTTO and DTTOMe. While the crystal structures of the latter compounds contain cofacial dimers, the crystal structure of DTTOMe4 comprises layers of molecules aligned in an antiparallel fashion. Intermediate neglect of differential overlap with single configuration interaction (INDO/SCI) calculations on the intermolecular interactions in the three crystal structures show that the different solid-state photoluminescence efficiencies of DTTOMe4, DTTOMe, and DTTO cannot be correlated with the different types of dipole-dipole alignment in the solid state. Instead, photoluminescence efficiencies correlate well with the rate of formation of nonradiatively decaying charge-transfer pairs upon photoexcitation. Because of larger intermolecular distances in DTTOMe4, the photoluminescence is less effectively quenched by charge-transfer processes than in DTTOMe and DTTO.

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