Combined experimental-theoretical NMR study on 2,5-bis(5-aryl-3- hexylthiophen-2-yl)-thiazolo[5,4-d]thiazole derivatives for printable electronics

S. Van Mierloo, V. Liégeois, J. Kudrjasova, Edith Botek, L. Lutsen, B. Champagne, D. Vanderzande, P. Adriaensens, W. Maes

Research output: Contribution to journalArticle

Abstract

Four 2,5-bis(5-aryl-3-hexylthiophen-2-yl)thiazolo[5,4-d]thiazole derivatives have been synthesized and thoroughly characterized. The extended aromatic core of the molecules was designed to enhance the charge transport characteristics, and solubilizing hexyl side chains were introduced on the thiophene subunits to enable possible integration of these semiconducting small molecules in printable electronics. Complete elucidation of the chemical structures by detailed one-dimensional/two-dimensional NMR spectroscopy is described, providing interesting input for chemical shift prediction software as well, because limited experimental data on these types of compounds are currently available. Furthermore, theoretical calculations have assisted experimental observations-giving support for the chemical shift assignment and providing a springboard for future screening and predictions-demonstrating the benefits of a coordinated theoretical-experimental approach.
Original languageEnglish
Pages (from-to)379-387
Number of pages9
JournalMagnetic Resonance in Chemistry
Volume50
Issue number5
DOIs
Publication statusPublished - 1 May 2012

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Thiazoles
Chemical shift
Electronic equipment
Nuclear magnetic resonance
Derivatives
Thiophenes
Molecules
Thiophene
Nuclear magnetic resonance spectroscopy
Charge transfer
Screening

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abstract = "Four 2,5-bis(5-aryl-3-hexylthiophen-2-yl)thiazolo[5,4-d]thiazole derivatives have been synthesized and thoroughly characterized. The extended aromatic core of the molecules was designed to enhance the charge transport characteristics, and solubilizing hexyl side chains were introduced on the thiophene subunits to enable possible integration of these semiconducting small molecules in printable electronics. Complete elucidation of the chemical structures by detailed one-dimensional/two-dimensional NMR spectroscopy is described, providing interesting input for chemical shift prediction software as well, because limited experimental data on these types of compounds are currently available. Furthermore, theoretical calculations have assisted experimental observations-giving support for the chemical shift assignment and providing a springboard for future screening and predictions-demonstrating the benefits of a coordinated theoretical-experimental approach.",
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Combined experimental-theoretical NMR study on 2,5-bis(5-aryl-3- hexylthiophen-2-yl)-thiazolo[5,4-d]thiazole derivatives for printable electronics. / Van Mierloo, S.; Liégeois, V.; Kudrjasova, J.; Botek, Edith; Lutsen, L.; Champagne, B.; Vanderzande, D.; Adriaensens, P.; Maes, W.

In: Magnetic Resonance in Chemistry, Vol. 50, No. 5, 01.05.2012, p. 379-387.

Research output: Contribution to journalArticle

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AU - Van Mierloo, S.

AU - Liégeois, V.

AU - Kudrjasova, J.

AU - Botek, Edith

AU - Lutsen, L.

AU - Champagne, B.

AU - Vanderzande, D.

AU - Adriaensens, P.

AU - Maes, W.

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