Design and Synthesis of Fluorinated Porous Molecular Crystals

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dc.contributor.advisorMiljanić, Ognjen Š.
dc.contributor.committeeMemberDaugulis, Olafs
dc.contributor.committeeMemberWu, Judy I-Chia
dc.contributor.committeeMemberHalasyamani, P. Shiv
dc.contributor.committeeMemberRimer, Jeffrey D.
dc.creatorHashim, Mohamed I. 1985-
dc.date.accessioned2020-01-04T00:00:19Z
dc.date.available2020-01-04T00:00:19Z
dc.date.createdDecember 2018
dc.date.issued2018-12
dc.date.submittedDecember 2018
dc.date.updated2020-01-04T00:00:19Z
dc.description.abstractPorous molecular crystals are an emerging class of porous materials that are built from discrete molecules rather than being polymeric in nature. In this thesis, the effects of the molecular structure of the precursors on the formation of porous solid-state structures were examined. One of the trigonal fluorinated porous molecular crystals displayed aggregation-induced emission and this discovery was studied in more detail. Chapter One, summarizes the research literature that discusses the work and applications conducted on crystalline porous materials. The porous materials that are discussed herein are metal-organic frameworks, covalent organic frameworks, and porous organic molecular crystals that are held together by non-covalent interactions. Chapter Two, discusses the synthetic strategies and methodology utilized in the preparation of six novel fluorinated porous molecular crystal precursors of different geometries. The insights and lessons learned from the successful and failed synthetic attempts are also discussed. Chapter Three, describes the solvothermal synthesis and characterizations of molecular crystals. The gas sorption isotherms and hydrophobic properties of the porous variants are also discussed. Chapter Four, describes the investigations of the fluorescent properties of fluorinated trispyrazole compounds that make up porous molecuclar crystal frameworks. It was found that in a DMF/H2O mixed solvent system one of the compounds displays aggregation-induced emission (AIE), while its iso-structural counterpart does not. The reason for this difference was investigated. Further research conducted on the AIE active compound also led to the discovery that it can discriminate between dicarboxylic acids through assembly induced emissions. In summary, this study the grometry and dimensions of the precursors was varied, resulting in six crystallographically characterized derivatives. Among these derviatives two were found to be porous and posessed surface areas of 903 m2 g⁻1 and 1821 m2 g⁻1. It was also revealed that the rigid trigonal geometry plays a key role in the design and prepararation porous molecular crystals.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginborn digital
dc.format.mimetypeapplication/pdf
dc.identifier.citationPortions of this document appear in: Hashim, Mohamed I., Chia-Wei Hsu, Ha TM Le, and Ognjen Š. Miljanić. "Organic molecules with porous crystal structures." Synlett 27, no. 13 (2016): 1907-1918. And in: Hashim, Mohamed I., Ha TM Le, Teng-Hao Chen, Yu-Sheng Chen, Olafs Daugulis, Chia-Wei Hsu, Allan J. Jacobson et al. "Dissecting Porosity in Molecular Crystals: Influence of Geometry, Hydrogen Bonding, and [π··· π] Stacking on the Solid-State Packing of Fluorinated Aromatics." Journal of the American Chemical Society 140, no. 18 (2018): 6014-6026. And in: Zhang, Zhenglin, Mohamed I. Hashim, and Ognjen Š. Miljanić. "Aggregation-induced emission in precursors to porous molecular crystals." Chemical Communications 53, no. 72 (2017): 10022-10025.
dc.identifier.urihttps://hdl.handle.net/10657/5702
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.subjectPorous Molecular Crystals
dc.subjectPorous materials
dc.subjectFluorinated Compounds
dc.subjectPorosity
dc.titleDesign and Synthesis of Fluorinated Porous Molecular Crystals
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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