Synthesis of organic compounds for two-photon initiated polymerization and molecular recognition
| dc.contributor.advisor | Anslyn, Eric V. | en |
| dc.creator | Postnikova, Brenda Jean | en |
| dc.date.accessioned | 2008-08-28T21:37:23Z | en |
| dc.date.available | 2008-08-28T21:37:23Z | en |
| dc.date.issued | 2003 | en |
| dc.description | text | en |
| dc.description.abstract | In section I, three-dimensional polymeric objects were fabricated using two-photon initiated polymerization (TPIP) with a two-photon absorbing chromophore and an acrylate resin. The feasibility of fabricating polymeric features on the nanoscale was explored using an enhanced field generated at the apex of a gold tip as the excitation source, as used in near-field excitation (NFE). In section II, C3-symmetric chiral receptors were used to direct enantioselective enolate alkylation. A series of host compounds was synthesized and 1:1 host to enolate binding was observed by 1 H NMR titration experiments. A moderate increase in the enantioselectivity of the alkylation of 2-acetylcyclohexanone was observed in the presence of host 2.22. Also in section II, the use of enolate stabilization via charge-pairing was investigated for the reduction of the pKa of 2- acetylcyclopentanone. In the presence of host 3.12, the pKa of 2- acetylcyclopentanone was reduced by 10 pKa units. In comparison with the 2.9 pKa unit shift observed with host 3.11, this result suggests that charge-pairing is more effective in stabilizing enolates in enzyme active sites than traditional hydrogen bonding. | |
| dc.description.department | Chemistry and Biochemistry | en |
| dc.description.department | Chemistry | en |
| dc.format.medium | electronic | en |
| dc.identifier | b57186029 | en |
| dc.identifier.oclc | 56889718 | en |
| dc.identifier.proqst | 3118060 | en |
| dc.identifier.uri | http://hdl.handle.net/2152/863 | en |
| dc.language.iso | eng | en |
| dc.rights | Copyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works. | en |
| dc.subject.lcsh | Organic compounds--Synthesis | en |
| dc.subject.lcsh | Photopolymerization | en |
| dc.title | Synthesis of organic compounds for two-photon initiated polymerization and molecular recognition | en |
| dc.type.genre | Thesis | en |