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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
Author(s) -
Van Mierloo S.,
Liégeois V.,
Kudrjasova J.,
Botek E.,
Lutsen L.,
Champagne B.,
Vanderzande D.,
Adriaensens P.,
Maes W.
Publication year - 2012
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3812
Subject(s) - thiazole , chemistry , thiophene , aryl , molecule , combinatorial chemistry , small molecule , chemical shift , computational chemistry , density functional theory , organic electronics , stereochemistry , organic chemistry , voltage , transistor , physics , quantum mechanics , biochemistry , alkyl
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. Copyright © 2012 John Wiley & Sons, Ltd.