Synthesis of novel proton-ionizable calix[4]arenes
| dc.contributor.committeeChair | Bartsch, Richard A. | |
| dc.contributor.committeeMember | Li, Guigen | |
| dc.contributor.committeeMember | Birney, David M. | |
| dc.creator | Shen, Xin | |
| dc.date.accessioned | 2016-11-14T23:15:59Z | |
| dc.date.available | 2012-06-01T16:53:16Z | |
| dc.date.available | 2016-11-14T23:15:59Z | |
| dc.date.issued | 2006-05 | |
| dc.degree.department | Chemistry | |
| dc.description.abstract | A series of p-tert-butylcalix[4]arenes was synthesized with enlongated acidic groups, 4-oxybutanoic acid, 5-oxypentanoic acid, N-(X)sulfonyl 4-oxybutanamide and N-(X)sulfonyl 5-oxypentanamide, on the lower rim as proton ionizable groups with or without tert-butyl groups on the upper rim. Calix[4]arenes with butoxy groups instead of methoxy groups, which are fixed in the cone conformation, are also prepared. An efficient synthesis route for p-benzoyl and p-benzyl-substituted calix[4]arenes is reported. Further preparation of novel proton-ionizable calix[4]arenes with four benzoyl or benzyl groups on the upper rim and two methoxy groups and two N-(X)sulfonyl carboxamide groups on the lower rim are described. Di-p-benzoyl- and di-p-benzyl substituted calix[4]arenes were synthesized to achieve individual control of the para substituent of the four aromatic rings and further preparation of proton-ionizable calix[4]arenes with two methoxy groups and two N-(X)sulfonyl carboxamide groups on the lower rim was achieved. The syntheses of di-p-nitrocalix[4]arenes was accomplished by ipso-substitution. Proton-ionizable calix[4]arenes with two tert-butyl groups and two nitro groups on the upper rim and either one methoxy group and two N-(X)sulfonyl carboxamide groups or two methoxy groups and one N-(X)sulfonyl carboxamide group on the lower rim were synthesized. | |
| dc.format.mimetype | application/pdf | |
| dc.identifier.uri | http://hdl.handle.net/2346/1063 | |
| dc.language.iso | eng | |
| dc.rights.availability | Unrestricted. | |
| dc.subject | Proton ionizable groups | |
| dc.subject | Calix[4]arenes | |
| dc.subject | Synthesis | |
| dc.title | Synthesis of novel proton-ionizable calix[4]arenes | |
| dc.type | Dissertation |