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Topic

Water-soluble photoswitchable supramolecular hosts based on the hemiindigo chromophore

Department of Chemistry

Date & location

• Monday, August 12, 2024
• 1:00 P.M.
• Elliott Building, Room 230

Examining Committee

Supervisory Committee

• Dr. Fraser Hof, Department of Chemistry, ·¬ÇÑÉçÇø (Supervisor)
• Dr. Scott McIndoe, Department of Chemistry, UVic (Member)

External Examiner

• Dr. Alisdair Boraston, Department of Biochemistry and Microbiology, UVic

Chair of Oral Examination

• Dr. Christo Papadopoulos, Department of Electrical and Computer Engineering, UVic

Abstract

The constant search for new and unusual hosts is what pushing supramolecular chemistry forwards. The scope of their applications is immense: drug recognition and reversal, novel materials, catalysis, purification and separation of chemicals etc., not to mention a fundamental insight into chemical and biological systems that can be gained by studying them. Sulfonated calixarenes constitute an important family of such hosts. Their exceptional binding properties coupled with water-solubility, high stability and endless potential for synthetic modifications make them perfect candidates for study. There are numerous examples of those macrocycles, modified in a way that introduces a fluorescent chromophore, enabling them to be used as detectors for various guests. Yet, cases of them being able to change their properties upon irradiation with light – having a photoswitchable chromophore – remain particularly scarce. This work attempts to present such system – a pair of sulfonated calixarenes, calix[4] and calix[5]arene with a hemiindigo moieties installed on the upper rim. Here we demonstrate their synthesis, as well as a study into their photophysical and supramolecular properties. Various advanced NMR techniques such as DOSY and NOESY were used in conjunction to demonstrate differences in their aggregation.