Synthesis and applications of novel resorcin[4]arene cavitands

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dc.contributor.author Leaym, Xiaoxuan
dc.date.accessioned 2008-05-12T20:51:56Z
dc.date.available 2008-05-12T20:51:56Z
dc.date.issued 2008-05-12T20:51:56Z
dc.identifier.uri http://hdl.handle.net/2097/745
dc.description.abstract A series of methylene-bridged resorcin[4]arenes featuring electrochemically active and hydrophilic viologene-units chemically attached to their "rim"-regions have been synthesized. Depending on the choices of pendent groups (feet) and the numbers of positive charges on the "rim" (four or eight), moderate to very good solubilities in water were obtained. A fluorescent coumarin tag designed for the purpose of photophysical studies was chemically linked to the feet of some of the synthesized resorcin[4]arenes. These compounds were designed to act as guests in mycobacterial channel proteins (channel blockers). The proven host-guest interaction between resorcin[4]arenes and the mycobacterial porin MspA suggests potential application of my research in TB treatment. Both, hydrophilic nutrients and metabolites have to diffuse through the porin channels of mycobacteria because of the lack of an active transport mechanism. If these channels are successfully blocked, the mycobacteria have either to synthesize new channels, which make their outer membrane more susceptible to conventional antibiotics, or they become dormant. (3,3'-dimethyl)-4,4'-bipyridinium units are very suitable electron relays. They can be reduced stepwise to viologen monoradical cations and then to uncharged viologen diradicals which possess highly negative redox potentials, allowing them to reduce C-Cl bonds. Therefore, the deep cavitand viologen resorcin[4]arenas, are expected to bind and detoxify chlorinated hydrocarbons by reductive dechlorination. In this work, the step wise reduction process of viologen- resorcin[4]arenes and the formation of negative redox potentials of double-reduced viologen resorcin[4]arenes are demonstrated by electrochemistry studies. These results encourage future studies toward an efficient electrocatalytic system for the reductive dehalogenation of organic compounds. Besides highly charged resorcin[4]arene cavitands, the synthesis of a thiol-footed resorcin[4]arene was also attempted. The product was used for gold nanoparticle binding studies. The results of the photochemistry measurements provided a proof-of-concept for using the emission of gold nanoparticles in chemical sensors after covering their surfaces with thiol-footed resorcin[4]arenes. Two heterocylic resorcin[4]arene cavitands were synthesized for DNA-intercalation studies. The results of the photochemical measurements suggested binding between DNA and the heterocyclic resorcin[4]arenes and provided proof-of-principle for potential drug applications of this type of macrocycle. en
dc.description.sponsorship NSF_EPSCoR en
dc.language.iso en_US en
dc.publisher Kansas State University en
dc.subject Resorcinarene en
dc.subject TB_Channel Blocker en
dc.subject Supramolecular Chemistry en
dc.subject Physical Organic Chemistry en
dc.subject Organic Synthesis en
dc.subject DNA-Intercalator en
dc.title Synthesis and applications of novel resorcin[4]arene cavitands en
dc.type Dissertation en
dc.description.degree Doctor of Philosophy en
dc.description.level Doctoral en
dc.description.department Department of Chemistry en
dc.description.advisor Stefan Bossmann en
dc.subject.umi Chemistry, Organic (0490) en
dc.subject.umi Chemistry, Pharmaceutical (0491) en
dc.subject.umi Chemistry, Physical (0494) en
dc.date.published 2008 en
dc.date.graduationmonth May en


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