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Pathway Complexity in the Enantioselective Self-Assembly of Functional Carbonyl-Bridged Triarylamine Trisamides

Title data

Haedler, Andreas T. ; Meskers, Stefan C. J. ; Zha, R. Helen ; Kivala, Milan ; Schmidt, Hans-Werner ; Meijer, E. W.:
Pathway Complexity in the Enantioselective Self-Assembly of Functional Carbonyl-Bridged Triarylamine Trisamides.
In: Journal of the American Chemical Society. Vol. 138 (2016) Issue 33 . - pp. 10539-10545.
ISSN 1520-5126
DOI: https://doi.org/10.1021/jacs.6b05184

Abstract in another language

Functional supramolecular systems like carbonyl-bridged triarylamine (CBT) trisamides are known for their long-range energy transport at room temperature. Understanding the complex self-assembly processes of this system allows for control over generated structures using controlled supramolecular polymerization. Here, we present two novel CBT trisamides with (S)- or (R)-chiral side chains which show a two-pathway self-assembly behavior in solution. Depending on the thermal profile during the self-assembly process, two different stable states are obtained under otherwise identical conditions. A kinetically trapped state A is reached upon cooling to 7 °C, via a proposed isodesmic process. In addition, there is a thermodynamically stable state B at 7 °C that is induced by first undercooling to −5 °C, via a nucleation-elongation mechanism. In both cases, helical supramolecular aggregates comprising H-aggregated CBTs are formed. Additionally, controlled supramolecular polymerization was achieved by mixing the two different states (A and B) from the same enantiomer, leading to a conversion of the kinetically trapped state to the thermodynamically stable state. This process is highly enantioselective, as no conversion is observed if the two states consist of opposite enantiomers. We thus show the importance and opportunities emerging from understanding the pathway complexity of functional supramolecular systems.

Further data

Item Type: Article in a journal
Refereed: No
Additional notes: PMID: 27462007
Institutions of the University: Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I > Chair Macromolecular Chemistry I - Univ.-Prof. Dr. Hans-Werner Schmidt
Profile Fields
Profile Fields > Advanced Fields
Profile Fields > Advanced Fields > Polymer and Colloid Science
Research Institutions
Research Institutions > Research Centres
Research Institutions > Research Centres > Bayreuth Institute of Macromolecular Research - BIMF
Research Institutions > Research Centres > Bayreuth Center for Colloids and Interfaces - BZKG
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 03 Apr 2019 10:12
Last Modified: 03 Apr 2019 10:12
URI: https://eref.uni-bayreuth.de/id/eprint/35993