Binding of azobenzene derivatives onto macrocyclic surfaces

Maike Wiemann

Research output: ThesisPhD Thesis - Research UT, graduation UT

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The research described in this thesis is focused on stimuli-responsive macrocyclic supramolecular surfaces. Several macrocyclic host systems such as cucurbit[n]uril and cyclodextrin systems have been employed to host mono-, bi- and trivalent guests that are sensitive to stimuli such as light and electrochemistry. Such supramolecular stimuli-responsive surfaces are of fundamental interest and have potential for application in cell-instructive interfaces. Cucurbit[n]urils are in the focus of interest since two decades and enjoy increasing enthusiasm due to their potential application in fabricating biological surfaces, which was reviewed in chapter 1. In chapter 2, a new heteroternary complex was described using arylazopyrazole based light switches as guests for CB[8]. The potential for biological application of these complexes was shown with cellular immobilization and release experiments. Multivalent azobenzene derivatives were synthesized and their binding to CB[8] based surfaces was characterized in chapter 3. Chapter 4 describes the efforts to achieve patterning of multivalent ligands on antifouling surfaces. In chapter 5, patterns of CB[8]-mediated heteroternary complexes were made and used to investigate their dynamics on surfaces. Although more experiments are needed for a complete picture of the dynamics on CB[8] surfaces, azopyridine guests were moving slowly along the surface. Strategies to selectively tune surface properties using stimuli-responsiveness were investigated in chapter 6. Application of different stimuli to surface-bound heterodivalent molecules have influence on their binding strength, orientation and thus as well on the surface properties.
Overall, this thesis presents a perspective on several dynamic macrocyclic supramolecular systems. The work on the stimuli-responsive and multivalent guests demonstrates the potential to tune the interaction strength of supramolecular assemblies on surfaces and enables controlled association and dissociation. Combined with lithographic techniques, such as microcontact printing and micromolding in capillaries, new approaches for supramolecular architectures on interfaces involving CB[8] are described and can be integrated in the future design of molecular devices and dynamic materials.
Original languageEnglish
QualificationDoctor of Philosophy
Awarding Institution
  • University of Twente
  • Jonkheijm, P., Supervisor
Award date17 Jan 2019
Place of PublicationEnschede
Print ISBNs978-90-365-4699-7
Publication statusPublished - 17 Jan 2019


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