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Kautny P, Glöcklhofer F, Kader T, et al. Charge-transfer states in triazole linked donor-acceptor materials: strong effects of chemical modification and solvation. Phys Chem Chem Phys. 2017;19(27):18055-18067doi: 10.1039/c7cp01664f.
Kautny, P., Glöcklhofer, F., Kader, T., Mewes, J. M., Stöger, B., Fröhlich, J., Lumpi, D., & Plasser, F. (2017). Charge-transfer states in triazole linked donor-acceptor materials: strong effects of chemical modification and solvation. Physical chemistry chemical physics : PCCP, 19(27), 18055-18067. https://doi.org/10.1039/c7cp01664f
Kautny, Paul, et al. "Charge-transfer states in triazole linked donor-acceptor materials: strong effects of chemical modification and solvation." Physical chemistry chemical physics : PCCP vol. 19,27 (2017): 18055-18067. doi: https://doi.org/10.1039/c7cp01664f
Kautny P, Glöcklhofer F, Kader T, Mewes JM, Stöger B, Fröhlich J, Lumpi D, Plasser F. Charge-transfer states in triazole linked donor-acceptor materials: strong effects of chemical modification and solvation. Phys Chem Chem Phys. 2017 Jul 21;19(27):18055-18067. doi: 10.1039/c7cp01664f. Epub 2017 Jul 03. PMID: 28671704.
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Phys Chem Chem Phys. 2017 Jul 21;19(27):18055-18067. doi: 10.1039/c7cp01664f. Epub 2017 Jul 03.

Charge-transfer states in triazole linked donor-acceptor materials: strong effects of chemical modification and solvation.

Physical chemistry chemical physics : PCCP

Paul Kautny, Florian Glöcklhofer, Thomas Kader, Jan-Michael Mewes, Berthold Stöger, Johannes Fröhlich, Daniel Lumpi, Felix Plasser

Affiliations

  1. Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, A-1060 Vienna, Austria. [email protected].
  2. Centre for Theoretical Chemistry and Physics, The New Zealand Institute for Advanced Study (NZIAS), Massey University Albany, Private Bag 102904, Auckland 0745, New Zealand.
  3. X-ray Center, TU Wien, Getreidemarkt 9, A-1060 Vienna, Austria.
  4. Institute of Theoretical Chemistry, Faculty of Chemistry, University of Vienna, Währinger Str. 17, A-1090 Vienna, Austria. [email protected].

PMID: 28671704 DOI: 10.1039/c7cp01664f

Abstract

A series of 1,2,3-triazole linked donor-acceptor chromophores are prepared by Click Chemistry from ene-yne starting materials. The effects of three distinct chemical variations are investigated: enhancing the acceptor strength through oxidation of the sulphur atom, alteration of the double bond configuration, and variation of the triazole substitution pattern. A detailed photophysical characterization shows that these alterations have a negligible effect on the absorption while dramatically altering the emission wavelengths. In addition, strong solvatochromism is found leading to significant red shifts in the case of polar solvents. The experimental findings are rationalized and related to the electronic structure properties of the chromophores by time-dependent density functional theory as well as the ab initio algebraic diagrammatic construction method for the polarization propagator in connection with a new formalism allowing to model the influence of solvation onto long-lived excited states and their emission energies. These calculations highlight the varying degree of intramolecular charge transfer character present for the different molecules and show that the amount of charge transfer is strongly modulated by the conducted chemical modifications, by the solvation of the chromophores, and by the structural relaxation in the excited state. It is, furthermore, shown that enhanced charge separation, as induced by chemical modification or solvation, reduces the singlet-triplet gaps and that two of the investigated molecules possess sufficiently low gaps to be considered as candidates for thermally activated delayed fluorescence.

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