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Tyrosine Side-Chain Functionalities at Distinct Positions Determine the Chirooptical Properties and Supramolecular Structures of Pentameric Oligothiophenes
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, Faculty of Science & Engineering.
Linköping University, Department of Physics, Chemistry and Biology, Biophysics and bioengineering. Linköping University, Faculty of Science & Engineering.ORCID iD: 0000-0002-1781-1489
KTH Royal Inst Technol, Sweden.
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, Faculty of Science & Engineering.ORCID iD: 0000-0002-4303-4783
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2020 (English)In: ChemistryOpen, ISSN 2191-1363, Vol. 9, no 11, p. 1100-1108Article in journal (Refereed) Published
Abstract [en]

Control over the photophysical properties and molecular organization of pi-conjugated oligothiophenes is essential to their use in organic electronics. Herein we synthesized and characterized a variety of anionic pentameric oligothiophenes with different substitution patterns of L- or D-tyrosine at distinct positions along the thiophene backbone. Spectroscopic, microscopic, and theoretical studies of L- or D-tyrosine substituted pentameric oligothiophene conjugates revealed the formation of optically active pi-stacked self-assembled aggregates under acid conditions. The distinct photophysical characteristics, as well as the supramolecular structures of the assemblies, were highly influenced by the positioning of the L- or D-tyrosine moieties along the thiophene backbone. Overall, the obtained results clearly demonstrate how fundamental changes in the position of the enantiomeric side-chain functionalities greatly affect the optical properties as well as the architecture of the self-assembled supramolecular structures.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2020. Vol. 9, no 11, p. 1100-1108
Keywords [en]
oligothiophenes; chirality; induced circular dichroism; self-assembly; chiro-optical aggregates
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-173000DOI: 10.1002/open.202000144ISI: 000593986800003PubMedID: 33163327OAI: oai:DiVA.org:liu-173000DiVA, id: diva2:1522869
Available from: 2021-01-27 Created: 2021-01-27 Last updated: 2021-02-19

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