An efficient lactone-to-lactam conversion for the synthesis of thiophene Pechmann lactam and the characterization of polymers thereof. Issue 42 (4th October 2018)

• Record Type: Journal Article
• Authors: Lee, Kyu Cheol; Lee, Hae Rang; Kang, So-Huei; Lee, Jungho; Park, Young IL; Noh, Seung Man; Oh, Joon Hak; Yang, Changduk
• Is Part Of: Polymer chemistry. Volume 9:Issue 42(2018)
• Page Start: 5234
• Page End: 5241
• Publication Date: 2018-10-04
• Subjects: Polymers -- Periodicals; Macromolecules -- Periodicals; Polymerization -- Periodicals; 547.705
• DOI: 10.1039/c8py00997j
• Languages: English
• ISSNs: 1759-9954

Abstract

Abstract : We proposed an efficient methodology for Pechmann lactone-to-lactam conversion for various molecular applications. Abstract : Despite having unique structural features, e.g., high co-planarity and a strong polar bicyclic lactam structure, thiophene bipyrrolylidene-2, 2′(1 H, 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 cm 2 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.