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

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.

Synthesis, 1H and 13C NMR assignment and electrochemical properties of novel thiophene-thiazolothiazole oligomers and polymers.

Novel hexyl-substituted bisthiophene compounds containing a thiazolothiazole(5,4-d) unit have been explored. The molecules are soluble in common organic solvents, which would enhance their chance of possible integration in printable electronics. Synthesis and complete elucidation of the chemical structures by detailed 1D/2D NMR spectroscopy are described. This provides interesting input for chemical shift prediction software, because few experimental data on this type of compounds are available. Furthermore, the potential n-type character of these derivatives is verified using electrochemical measurements. In addition, the low-bandgap character of conjugated polymers containing the thiazolothiazole unit is demonstrated by performing an electropolymerization.