Synthesis and electrochemical properties of calix[4]arene-triester-monoquinones
- Authors
- Oh, WS; Chung, TD; Kim, J; Kim, HS; Kim, H; Hwang, D; Kim, K; Rha, SG; Choe, JI; Chang, Suk-Kyu
- Issue Date
- 1998
- Publisher
- GORDON BREACH SCI PUBL LTD
- Keywords
- calix[4]arene; monoquinone; Na+ ion; ionophore; electrochemistry
- Citation
- SUPRAMOLECULAR CHEMISTRY, v.9, no.3, pp 221 - 229
- Pages
- 9
- Journal Title
- SUPRAMOLECULAR CHEMISTRY
- Volume
- 9
- Number
- 3
- Start Page
- 221
- End Page
- 229
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/43653
- DOI
- 10.1080/10610279808034990
- ISSN
- 1061-0278
1029-0478
- Abstract
- Calix[4]arene-based monoquinones having three efficient ligating groups of alkoxycarbomethyl ethers were prepared and their ionophoric properties were investigated by electrochemical technique. Calix[4]-triester-monoquinones 3a and 3b were prepared from calix[4]arene and p-tert-butylcalix[4]arene by the selective trialkylation followed by oxidation with Tl(NO3)(3) and Tl(CF3CO2)(3), respectively. X-ray crystal structural analysis revealed that the ligand 3a adopted a partial cone conformation with an anti quinone moiety. MM+ calculations suggested that the energy difference between the two conformations is relatively small (<3.5 kcal mole(-1)). Electrochemical studies also showed that the monoquinones 3a and 3b form strong complexes with Na+ ion, and the positive shifts in the reduction potential exceeded those of the closely related diquiones 5a and 5b.
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