Synthesis and Characterization of Soluble Low-Bandgap Oligothiophene-[all]-S,S-dioxides-Based Conjugated Oligomers and Polymers

TitleSynthesis and Characterization of Soluble Low-Bandgap Oligothiophene-[all]-S,S-dioxides-Based Conjugated Oligomers and Polymers
Publication TypeJournal Article
Year of Publication2011
AuthorsE. Amir, Kulandaivelu Sivanandan, J.E. Cochran, John J. Cowart, S.Y. Ku, Jung Hwa Seo, M.L. Chabinyc, and C.J. Hawker
JournalJOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume49
Pagination1933-1941
Date PublishedMAY 1
ISSN0887-624X
Keywordsconjugated polymers, crystal structures, oligomers, synthesis, UV-vis spectroscopy
AbstractThe synthesis and characterization of a new family of soluble oligothiophene-S,S-dioxides and their use as building blocks to form polythiophene-S,S-dioxides via microwave-assisted Stille coupling polymerization are described. Incorporation of the sulfone group into the polythiophene backbone leads to narrowing of the polymer bandgap, and while the energies of both Frontier orbitals in polythiophene-S,S-dioxide are lower with respect to polythiophenes, this tendency is considerably stronger for the lowest unoccupied molecular orbital than for the highest occupied molecular orbital, resulting in greater electron-accepting ability. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 1933-1941, 2011
DOI10.1002/pola.24641