Synthesis and cation binding properties of bis-bridged calix[6]arenes
| dc.contributor.author | Farmer, Dustin Blaine | |
| dc.date.accessioned | 2021-11-03T13:51:35Z | |
| dc.date.available | 2021-11-03T13:51:35Z | |
| dc.date.issued | 1999-12 | |
| dc.description.abstract | Calixarenes have been studied and utilized for their molecular recognition properties. A total of four bis-bridged calix[6]arenes have been synthesized and their metal binding properties and structural conformations were studied in solid, solution, and gas phase. Methods of testing include: NMR titrations, liquid-liquid extractions, x-ray crystallography, and electrospray ionization-MS. A dialkylated calix[6]arene was used as the principle starting material which predisposed the four remaining phenolic hydroxyl groups for placement of two bis-electrophiles. The bis-electrophiles were triethylene glycol di-p-tosylate, α,α-di-bromomethyl-m-xylene, and 2,6-bis(bromomethyl) pyridine. All of the compounds tested, with the exception of the bis-xylenyl, formed 1:1 complexes. The bis-xylenyl calix[6]arene is a poor cation binder that is conformationally mobile at room temperature. In contrast the bis-pyridinyl calix[6]arene was a non-selective strong binder of all alkali metal ions. Both bis-bridged aromatic compounds were in a 1,2,3-alternate conformation. Also synthesized were bis-crown-4-calix[6]arene in the cone and 1,2,3-alternate conformation. The calixcrown conformers were selective for the larger alkali metals, cesium and rubidium, with the Cs+/Na+ selectivity of the cone being 1,400 and that of the 1,2,3-alternate being 144, in solution. Similar results were observed in gas phase competition studies where both conformers exhibited exclusive Cs+ selectivity over Rb+ and a selectivity trend for consecutive larger cations in competition mixtures of Na+/K+, and K+/Rb+. | |
| dc.description.department | Chemistry and Biochemistry | |
| dc.format | Text | |
| dc.format.extent | 86 pages | |
| dc.format.medium | 1 file (.pdf) | |
| dc.identifier.citation | Farmer, D. B. (1999). Synthesis and cation binding properties of bis-bridged calix[6]arenes (Unpublished thesis). Southwest Texas State University, San Marcos, Texas. | |
| dc.identifier.uri | https://hdl.handle.net/10877/14768 | |
| dc.language.iso | en | |
| dc.subject | calixarenes | |
| dc.subject | synthesis | |
| dc.subject | calix[6]arenes | |
| dc.subject | gas phase | |
| dc.title | Synthesis and cation binding properties of bis-bridged calix[6]arenes | |
| dc.type | Thesis | |
| thesis.degree.department | Chemistry | |
| thesis.degree.grantor | Southwest Texas State University | |
| thesis.degree.level | Masters | |
| thesis.degree.name | Master of Science |
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