Cyclotetrabenzoin: Esterification, Hosts for Thin Guests, Purification, and By-Product Analysis

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dc.contributor.advisorMiljanić, Ognjen Š.
dc.contributor.committeeMemberGilbertson, Scott R.
dc.contributor.committeeMemberWu, Judy I-Chia
dc.contributor.committeeMemberZastrow, Melissa L.
dc.contributor.committeeMemberRimer, Jeffrey D.
dc.creatorPeterson, Corie
dc.date.accessioned2020-06-04T02:21:41Z
dc.date.available2020-06-04T02:21:41Z
dc.date.createdMay 2020
dc.date.issued2020-05
dc.date.submittedMay 2020
dc.date.updated2020-06-04T02:21:41Z
dc.description.abstractPorous molecular crystals are a unique developing class of porous materials composed of discrete molecules. Macrocycles, which inherently have a central cavity, are a class of molecules that could be utilized in the continued development of porous molecular crystals. Cyclobenzoins are a class of macrocycles that were first reported in 2015 by the Miljanić group. Of the two reported macrocycles, cyclotribenzoin and cyclotetrabenzoin, this dissertation will mostly focus on our efforts to deepen the understanding and development of cyclotetrabenzoin. While published reaction conditions only produce one macrocycle with a 20% yield, analysis of other reaction components was attempted to determine what other products were being synthesized. A major limiting factor to studying cyclobenzoins is their insolubility in most common organic solvents. Previous modifications to cyclotetrabenzoin resulted in a major shape change in the pore, not enabling exploration of the intrinsic pore. Simple esterification with anhydrides was found to greatly increase cyclobenzoins solubility while not changing the shape of the intrinsic pore. Crystallization resulted in crystals with solvent molecules that could be removed resulting in a permanently porous crystal. A crystal structure was found to have CS2 molecules in the intrinsic pore, which was the first indication of a small molecule interacting with the pore. Continued exploration to crystalize thin guest molecules resulted in several host-guest complexes with terminal alkynes and nitriles as guests. Lastly, CO2 was shown in the crystal structure by X-ray crystallography and breakthrough curve analysis resulted in the ability to separate a N2/CO2 gas mixture.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginborn digital
dc.format.mimetypeapplication/pdf
dc.identifier.citationPortions of this document appear in: McHale, Corie M., Christina R. Stegemoller, Mohamed I. Hashim, Xiqu Wang, and Ognjen Š Miljanić. "Porosity and Guest Inclusion in Cyclobenzoin Esters." Crystal Growth & Design 19, no. 2 (2019): 562-567.
dc.identifier.urihttps://hdl.handle.net/10657/6696
dc.language.isoeng
dc.rightsThe 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).
dc.subjectbenzoin condensation
dc.subjectmacrocycle, carbon dioxide, porous molecular crystal
dc.subjectalkyne sensing
dc.titleCyclotetrabenzoin: Esterification, Hosts for Thin Guests, Purification, and By-Product Analysis
dc.type.dcmiText
dc.type.genreThesis
thesis.degree.collegeCollege of Natural Sciences and Mathematics
thesis.degree.departmentChemistry, Department of
thesis.degree.disciplineChemistry
thesis.degree.grantorUniversity of Houston
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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