Tyrosine Side‐Chain Functionalities at Distinct Positions Determine the Chirooptical Properties and Supramolecular Structures of Pentameric Oligothiophenes
Dr. Marcus Bäck,
Dr. Robert Selegård,
Yogesh Todarwal,
Dr. Sofie Nyström,
Prof. Patrick Norman,
Dr. Mathieu Linares,
Prof. Per Hammarström,
Prof. Mikael Lindgren,
Prof. K. Peter R. Nilsson
Affiliations
Dr. Marcus Bäck
Division of Chemistry, Department of Physics, Chemistry and Biology Linköping University 581 83 Linköpin Sweden
Dr. Robert Selegård
Division of Biophysics and Bioengineering, Department of Physics, Chemistry and Biology Linköping University 581 83 Linköping Sweden
Yogesh Todarwal
Department of Theoretical Chemistry and Biology KTH Royal Institute of Technology SE-106 91 Stockholm Sweden
Dr. Sofie Nyström
Division of Chemistry, Department of Physics, Chemistry and Biology Linköping University 581 83 Linköpin Sweden
Prof. Patrick Norman
Department of Theoretical Chemistry and Biology KTH Royal Institute of Technology SE-106 91 Stockholm Sweden
Dr. Mathieu Linares
Laboratory of Organic Electronics, ITN Linköping University SE-601 74 Norrköping Sweden
Prof. Per Hammarström
Division of Chemistry, Department of Physics, Chemistry and Biology Linköping University 581 83 Linköpin Sweden
Prof. Mikael Lindgren
Division of Chemistry, Department of Physics, Chemistry and Biology Linköping University 581 83 Linköpin Sweden
Prof. K. Peter R. Nilsson
Division of Chemistry, Department of Physics, Chemistry and Biology Linköping University 581 83 Linköpin Sweden
Abstract Control over the photophysical properties and molecular organization of π‐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 π‐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.
