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Author

Yang, Changduk
Advanced Tech-Optoelectronic Materials Synthesis Lab (ATOMS)
Research Interests
  • Optoelectronic materials synthesis/organic electronics, functionalization of carbonaceous solids, advanced materials chemistry, macromolecular chemistry

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An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof

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Title
An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof
Author
Lee, Kyu CheolLee, Hae RangKang, So-HueiLee, JunghoPark, Young ILNoh, Seung ManOh, Joon HakYang, Changduk
Issue Date
201811
Publisher
ROYAL SOC CHEMISTRY
Citation
POLYMER CHEMISTRY, v.9, no.42, pp.5234 - 5241
Abstract
Despite having unique structural features, e.g., high co-planarity and a strong polar bicyclic lactam structure, thiophene bipyrrolylidene-2,2′(1H,1′H)-dione (TBPD) has been less explored as a dye, mainly due to the quite low yield in its synthesis via lactone-to-lactam conversion. We reported an efficient methodology for synthesizing TBPD in high yield using p-toluenesulfonic acid monohydrate and a catalytic amount of 4-dimethylaminopyridine in the chloroform solvent. From the newly synthesized series of TBPD-based donor-acceptor-type polymers, we fabricated organic field-effect transistors (OFETs), which were subjected to a systematic study on the relationship between film microstructure and charge transport. Among them, the annealed PTBPD-Th film revealed a more ordered lamellar packing with the highest number of interlayers and preferential edge-on orientation, yielding the best hole mobility (up to 0.46 cm2 V−1 s−1). The improved synthesis of TBPD and our findings concerning related polymers could promote further research and development associated with the TBPD unit.
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DOI
http://dx.doi.org/10.1039/c8py00997j
ISSN
1759-9954
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