Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 35, Pages 8304-8312Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201900689
Keywords
dyes; pigments; hydrogen bonds; OFETs; semiconductors; supramolecular chemistry
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Funding
- French National Agency (ORION project) [ANR-13-PRGE-0001]
- Agence Nationale de la Recherche (ANR) [ANR-13-PRGE-0001] Funding Source: Agence Nationale de la Recherche (ANR)
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In the present study, we demonstrated the effect of hydrogen bonding in the semiconducting behaviour of a small molecule used in organic field-effect transistors (OFETs). For this study, the highly soluble dumbbell-shaped molecule, Boc-TATDPP based on a Boc-protected thiophene-diketopyrrolopyrrole (DPP) and triazatruxene (TAT) moieties was used. The two Boc groups of the molecule were removed by annealing at 200 degrees C, which created a strong hydrogen-bonded network of NH-TATDPP supported by additional pi-pi stacking. These were characterised by thermogravimetric analysis (TGA), UV/Vis and IR spectroscopy, XRD and high-resolution (HR)-TEM measurements. FETs were fabricated with the semiconducting channel made of Boc-TATDPP and NH-TATDPP separately. It is worth mentioning that the Boc-TATDPP film can be cast from solution and then annealed to get the other systems with NH-TATDPP. More importantly, NH-TATDPP showed significantly higher hole mobilities compared to Boc-TATDPP. Interestingly, the high hole mobility in the case of NH-TATDPP was unaffected upon blending with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). Thus, this robust hydrogen-bonded supramolecular network is likely to be useful in designing efficient and stable organic optoelectronic devices.
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