Perylene Bisimide Cyclophanes: Recognition of Alkaloids, Aggregation Behavior in Aqueous Environment and Guest-Mediated Chirality Transfer

Perylenbisimidcyclophane: Alkaloiderkennung, Aggregationsverhalten in wässriger Umgebung und gastvermittelter Chiralitätstransfer

Please always quote using this URN: urn:nbn:de:bvb:20-opus-200028
  • Inspired by the fact that sufficient solubility in aqueous media can be achieved by functional substitution of perylene bisimides (PBIs) with polar groups, one of the essential aims of this thesis was the design and successful synthesis of the new water-soluble PBI cyclophanes [2PBI]-1m and [2PBI]-1p, which are appended with branched, hydrophilic oligoethylene glycol (OEG) chains. Subsequently, the focus was set on the elucidation of properties of PBI cyclophane hosts which are also of relevance for recognition processes in biological systems.Inspired by the fact that sufficient solubility in aqueous media can be achieved by functional substitution of perylene bisimides (PBIs) with polar groups, one of the essential aims of this thesis was the design and successful synthesis of the new water-soluble PBI cyclophanes [2PBI]-1m and [2PBI]-1p, which are appended with branched, hydrophilic oligoethylene glycol (OEG) chains. Subsequently, the focus was set on the elucidation of properties of PBI cyclophane hosts which are also of relevance for recognition processes in biological systems. The performance of the new amphiphilic PBI cyclophane [2PBI]-1p as synthetic receptors for various natural aromatic alkaloids in aqueous media was thoroughly investigated. Alkaloids represent a prominent class of ubiquitous nitrogen containing natural compounds with a great structural variety and diverse biological activity. As of yet, no chromophore host acting as a molecular probe for a range of alkaloids such as harmine or harmaline is known. In addition, the self-association behavior of cyclophane host [2PBI]-1m and its reference monomer in water was studied in order to gain insights into the thermodynamic driving forces affecting the self-assembly process of these two PBI systems in aqueous environment. Moreover, the chirality transfer upon guest binding previously observed for a PBI cyclophane was investigated further. The assignment of the underlying mechanism of guest recognition to either the induced fit or conformational selection model was of particular interest.show moreshow less
  • Diese Arbeit befasste sich mit der Erforschung neuer Eigenschaften von Perylenbisimid-cyclophanwirten, zum Beispiel der Gast-Komplexierung in wässriger Umgebung (Kapitel 3.2) oder dem Einfluss von Wasser beim Selbstassemblierungsprozess einer dieser Wirte in Wasser (Kapitel 3.3). Weiterhin wurden der Chiralitätstransfer durch Gasterkennung und das der Wirt-Gast-Komplexbildung zugrunde liegende mechanistische Modell untersucht (Kapitel 3.4). ...

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Metadaten
Author: Meike Sapotta
URN:urn:nbn:de:bvb:20-opus-200028
Document Type:Doctoral Thesis
Granting Institution:Universität Würzburg, Fakultät für Chemie und Pharmazie
Faculties:Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Referee:Prof. Dr. Frank WürthnerORCiD
Date of final exam:2020/02/20
Language:English
Year of Completion:2021
DOI:https://doi.org/10.25972/OPUS-20002
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie
GND Keyword:Supramolekulare Chemie; Organische Chemie; Wirt-Gast-Beziehung
Tag:Chirality Transfer; Host-Guest-Chemistry; Self-Assembly in Water
Release Date:2021/02/22
Licence (German):License LogoCC BY-SA: Creative-Commons-Lizenz: Namensnennung, Weitergabe unter gleichen Bedingungen 4.0 International