Three-Way Chemoselectivity Switching through Coupled Equilibria in Complex System and Post-synthetic Modification of Cyclobenzoins

Everything around us is complex systems, including ant-hills, human economies, climate systems, nervous systems, and human beings. In order to understand complex systems often requires cross-disciplinary techniques that merge the knowledge from different fields such as mathematics, physics, biology, and chemistry. In terms of system chemistry, chemists study the interaction between molecules of the systems, which exhibit a new function from a set of molecules and emerging properties. This dissertation focuses on the use of diaza-Cope rearrange as a dynamic reaction in a complex system, as well as the synthesis of the derivatives of cyclotetrabenzoin. Chapter One, selected research literature about the application of coupled equilibrium which gives the emergence properties and also multi-responsive ability, are reviewed. Chapter Two, the diaza-Cope rearrangement is used as a dynamic reaction. In coupled equilibrium between diaza-Cope rearrangement and imine exchange, three imidazolidine products can be selectively controlled based on the addition time of the oxidant. Chapter Three, thiazolium salt as an alternative catalyst was used to synthesis cyclobenzoin. The intrinsic pore of cyclobenzoin has been expanded by using various types of dialdehyde, which increase the size of the central core of cyclobenzoin. Chapter Four, the new autocatalytic cycle based on diaza-Cope rearrangement, is illustrated. However, it has not been successful yet, but it inspired the synthesis of three new macrocycles. These latest three macrocycles are based on imine condensation of cyclotetrabenzoin, which may use as gas sorption materials.

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Houston

Year dc:date.issued

2021

Author dc:creator

• Puangsamlee, Thamon

Advisor dc:contributor.advisor

• Miljanić, Ognjen Š.

Committee members dc:contributor.committeemember

• Daugulis, Olafs
• Harth, Eva M.
• Zastrow, Melissa L.
• Robertson, Megan L.

• Coupled equilibrium, Cyclotetrabenzoin, Cyclobenzoin, Diaza-Cope rearrangement

Statement dc:rights

• The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. UH Libraries has secured permission to reproduce any and all previously published materials contained in the work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/10657/9271

OAI identifier oai:identifier

oai:uh-ir.tdl.org:10657/9271