Bridge-substituted calix[4]arenes: syntheses, conformations and application

被引：25

作者：

Fischer, Conrad ^{[1
]}

Gruber, Tobias ^{[1
]}

Seichter, Wilhelm ^{[1
]}

Weber, Edwin ^{[1
]}

机构：

[1] Tech Univ Bergakad Freiberg, Inst Organ Chem, D-09596 Freiberg, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 11期

关键词：

METAL-IONS; FLUORESCENT CHEMOSENSORS; PHOTOPHYSICAL PROPERTIES; MOLECULAR-MECHANICS; COMBINED NMR; BEARING; SENSOR; STABILITY; COMPLEXES; BEHAVIOR;

D O I：

10.1039/c1ob00028d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bridge-substituted calix[4]arene carboxylic acid, 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetramethoxy-calix[4]arene-2-carboxylic acid (1), can be readily converted to various esters 2-4 and reduced to the alcohol 5, which reacts with methyl iodide to give the ether 6. The alcohol can be dansylated to give 7, the fluorescence of which is selectively quenched by Cu(II) in acetonitrile. An attempt to convert the acid 1 to an amide resulted unexpectedly in the formation of a lactone 8. The conformational characteristics of 1-8 have been studied in solution and, in the cases of 2 and 4, in the solid state by determination of their single-crystal X-ray structures. With the exception of 8, in all these compounds the bridge substituent adopts an equatorial (lateral) orientation.

引用

页码：4347 / 4352

页数：6

共 40 条

[1] New fluorescent chemosensors for heavy metal ions based on functionalized pendant arm derivatives of 7-anthracenylmethyl-1,4,1 0-tri oxa-7,1 3-diazacyclopentadecane [J].

Aragoni, M. Caria ;

Arca, Massimiliano ;

Bencini, Andrea ;

Blake, Alexander J. ;

Caltagirone, Claudia ;

Danesi, Andrea ;

Devillanova, Francesco A. ;

Garau, Alessandra ;

Gelbrich, Thomas ;

Isaia, Francesco ;

Lippolis, Vito ;

Hursthouse, Michael B. ;

Valtancoli, Barbara ;

Wilson, Claire .

INORGANIC CHEMISTRY, 2007, 46 (19) :8088-8097

[2] ON THE CONFORMATIONAL ISOMERS IN TETRA-O-ALKYLCALIX[4]ARENES [J].

ARAKI, K ;

IWAMOTO, K ;

SHINKAI, S ;

MATSUDA, T .

CHEMISTRY LETTERS, 1989, (10) :1747-1750

[3] Stepwise synthesis and structural characterization of calix[4]- and calix[5]arenes bearing a functionalized arm on the methylene bridge. [J].

Bergamaschi, M ;

Bigi, F ;

Lanfranchi, M ;

Maggi, R ;

Pastorio, A ;

Pellinghelli, MA ;

Peri, F ;

Porta, C ;

Sartori, G .

TETRAHEDRON, 1997, 53 (38) :13037-13052

[4] Conformation, inversion barrier, and solvent-induced conformational shift in exo- and endo/exo-calix[4]arenes [J].

Biali, SE ;

Bohmer, V ;

Brenn, J ;

Frings, M ;

Thondorf, I ;

Vogt, W ;

Wohnert, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8350-8360

[5] Alkanediyl bridged calix[4]arenes: Synthesis, conformational analysis, and rotational barriers [J].

Biali, SE ;

Bohmer, V ;

Cohen, S ;

Ferguson, G ;

Gruttner, C ;

Grynszpan, F ;

Paulus, EF ;

Thondorf, I ;

Vogt, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :12938-12949

[6]

Desiraju G., 1999, WEAK HYDROGEN BOND

[7] Ratiometric Sensing of Hg2+ Based on the Calix[4]arene of Partial Cone Conformation Possessing a Dansyl Moiety [J].

Dhir, Abhimanew ;

Bhalla, Vandana ;

Kumar, Manoj .

ORGANIC LETTERS, 2008, 10 (21) :4891-4894

[8]

FINAN PA, 1962, J CHEM SOC, P2824

[9]

Fischer C., 2010, STRUCT CHEM COMMUN, V1, P43

[10] 2-(4-Bromobenzyl)-5,11,17,23-tetra-tert-butyl-25,26,27,28-tetramethoxycalix[4]arene [J].

Fischer, Conrad ;

Lin, Guisheng ;

Seichter, Wilhelm ;

Weber, Edwin .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 :01704-U3526

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