Threading of Conformationally Stable Calix[6]arene Wheels Substituted at the Methylene Bridges

被引：7

作者：

Bakic, Marina Tranfic ^{[1
]}

Iuliano, Veronica ^{[2
]}

Talotta, Carmen ^{[2
]}

Geremia, Silvano ^{[3
]}

Hickey, Neal ^{[3
]}

Spinella, Aldo ^{[2
]}

De Rosa, Margherita ^{[2
]}

Soriente, Annunziata ^{[2
]}

Gaeta, Carmine ^{[2
]}

Neri, Placido ^{[2
]}

机构：

[1] Univ Zagreb, Fac Food Technol & Biotechnol, Dept Chem & Biochem, Pierottijeva 6, Zagreb 10000, Croatia

[2] Univ Salerno, Dept Chem & Biol A Zambelli, Lab Supramol Chem, Via Giovanni Paolo II 132, I-84084 Salerno, Italy

[3] Univ Trieste, Dipartimento Sci Chim & Farmaceut, Ctr Eccellenza Biocristallog, Via L Giorgieri 1, I-34127 Trieste, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期

关键词：

CALIXARENES;

D O I：

10.1021/acs.joc.9b01779

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Calix[6]arenes disubstituted at the methylene bridges, which are stable in the cone or 1,2,3-alternate conformation, form pseudorotaxanes with dialkylammonium axles. The cone wheel-based pseudorotaxanes are 10-100 times more stable than those obtained with the native conformationally mobile calix[6]arene wheel, as a consequence of their higher degree of preorganization. The threading of conformationally stable 1,2,3-alternate calix[6]arenes is unprecedented in the literature. Therefore, very peculiar NMR features are here evidenced for this threading process involving the less symmetrical 1,2,3-alternate calix[6]arene conformation, which implies a peculiar rototranslation motion of the axle.

引用

页码：11922 / 11927

页数：6

共 17 条

[1]

[Anonymous], 2016, CALIXARENES

[2]

Arduini A., 2016, CALIXARENES, P761, DOI [10.1007/978-3-319-31867-7, DOI 10.1007/978-3-319-31867-7_29]

[3] Selective functionalization of methylene bridges of calix[6]arenes. Isolation and identification of stable conformers of methyl ether of p-tert-butylcalix[6]arene [J].