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Tyrosine Side-Chain...
Tyrosine Side-Chain Functionalities at Distinct Positions Determine the Chirooptical Properties and Supramolecular Structures of Pentameric Oligothiophenes
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- Bäck, Marcus (author)
- Linköpings universitet,Kemi,Tekniska fakulteten
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- Selegård, Robert (author)
- Linköpings universitet,Biofysik och bioteknik,Tekniska fakulteten
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- Todarwal, Yogesh (author)
- KTH,Teoretisk kemi och biologi,KTH Royal Inst Technol, Sweden
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- Nyström, Sofie (author)
- Linköpings universitet,Kemi,Tekniska fakulteten
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- Norman, Patrick (author)
- KTH,Teoretisk kemi och biologi,KTH Royal Inst Technol, Sweden
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- Linares, Mathieu (author)
- Linköpings universitet,Bioinformatik,Tekniska fakulteten
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- Hammarström, Per (author)
- Linköpings universitet,Kemi,Tekniska fakulteten
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- Lindgren, Mikael (author)
- Linköpings universitet,Kemi,Tekniska fakulteten,Norwegian Univ Sci & Technol, Norway
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- Nilsson, Peter (author)
- Linköpings universitet,Kemi,Tekniska fakulteten
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(creator_code:org_t)
- 2020-11-03
- 2020
- English.
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In: ChemistryOpen. - : Wiley. - 2191-1363. ; 9:11, s. 1100-1108
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- oligothiophenes
- chirality
- induced circular dichroism
- self-assembly
- chiro-optical aggregates
Publication and Content Type
- ref (subject category)
- art (subject category)
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