Date of Award


Publication Type

Master Thesis

Degree Name



Chemistry and Biochemistry


Loeb, Stephen




The development of synthetic molecules that exhibit reversible photoswitchable properties has become a topic of interest in many fields of research including (but not limited to) their incorporation into photochromic devices and molecular photoswitches. This thesis investigates the efficacy of two novel macrocycles synthesized based on two separate classes of photoswitches. Chapter 1 outlines an introduction into both the topics of mechanically interlocked molecules and their relationship to supramolecular chemistry as a whole, as well as the theory and overview of photoswitchable compounds in chemistry. Chapter 2 outlines the development of an azobenzene-based crown ether wheel and its association with a series of electron poor axles including the synthesis of a novel, complementary alkyne axle that was designed to freely allow cis/trans isomerism in an effort to synthesize a photoswitchable, [2]Pseudorotaxane. Chapter 3 outlines the synthesis of a bis(thienyl)ethene derived photoswitchable macrocycle and a related model compound and its ability to interact with a series of electron poor axles for the preparation of a novel, photoswitchable [2]Pseudorotaxane. Chapter 4 describes all the experimental data. This includes the synthetic procedures involved in the preparation of an extensive series of starting materials and synthetic intermediates as well as the preparation and testing of two novel, photoswitchable crown ether-based macrocycles.