Synthesis and cation binding properties of new arylazo-and heteroarylazotetrathiacalix[4]arenes

被引：24

作者：

Chakrabarti, A ^{[1
]}

Chawla, HM ^{[1
]}

Francis, T ^{[1
]}

Pant, N ^{[1
]}

Upreti, S ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 06期

关键词：

tetrathiacalix[4]arenes; chromogenic; diazotization; ionic recognition;

D O I：

10.1016/j.tet.2005.10.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New macrocyclic tetrathiacalix[4]arenes have been synthesized by incorporating arylazo-, thiazoleazo- and beta-naphthylazo- units in the tetrathiacalix[4]arene molecular architecture through diazotization and coupling reactions. The new compounds have been characterized by H-1 NMR, C-13 NMR and FAB-MS spectroscopic analysis. X-ray crystallography for one of the new dyes (4a) reveals that the compound is present in the cone conformation. The synthesized macrocycles have been examined for their binding with alkali (Li+, Na+, K+, Cs+ and Rb+), alkaline earth (Ca2+, Mg2+ and Ba2+) and transition metal cations (Cr3+, Fe2+, Co2+, Ni2+, Cu2+, Hg+, Hg2+, Pd2+ and Pt2+) by UV-visible spectroscopy to reveal selective bathochromic shifts for heavier alkali metal ions (cesium and rubidium) and palladium in a 1: 1 and 2:1 stoichiometry respectively. The study has a significant bearing on the development of useful ionic filters and sensor materials. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1150 / 1157

页数：8

共 30 条

[1] Thiacalixarenes:: Synthesis and structural analysis of thiacalix[4]arene and of p-tert-butylthiacalix[4]arene [J].

Akdas, H ;

Bringel, L ;

Graf, E ;

Hosseini, MW ;

Mislin, G ;

Pansanel, J ;

De Cian, A ;

Fischer, J .

TETRAHEDRON LETTERS, 1998, 39 (16) :2311-2314

[2] X-ray crystal and molecular structure of upper rim monoformylated calix[4] arene system [J].

Arora, V ;

Chawla, HM ;

Hundal, G .

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2004, 34 (07) :465-469

[3]

Arora V, 2003, INDIAN J CHEM A, V42, P3041

[4] MOLECULAR DIAGNOSTICS - SYNTHESIS OF NEW CHROMOGENIC CALIX[8]ARENES AS POTENTIAL REAGENTS FOR DETECTION OF AMINES [J].

CHAWLA, HM ;

SRINIVAS, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (22) :2593-2594

[5] Synthesis of new chromogenic calix[4]arenes bridged at the upper rim through bisazobiphenyl linkages [J].

Chawla, HM ;

Srinivas, K .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8464-8467

[6] The synthesis of some new derivatives of calix[4]arene containing azo groups [J].

Deligöz, H ;

Ercan, N .

TETRAHEDRON, 2002, 58 (14) :2881-2884

[7]

DESROCHES C, 2003, J CHEM SOC DA, P2085

[8] Homoleptic platinum(II) and palladium(II) complexes of 1,5,9-trithiacyclododecane:: the crystal structures of [Pt(12S3)2](PF6)2 • 2CH3NO2 and [Pd(12S3)2](BF4)2 • 0.5H2O [J].

Grant, GJ ;

Goforth, AM ;

VanDerveer, DG ;

Pennington, WT .

INORGANICA CHIMICA ACTA, 2004, 357 (07) :2107-2114

[9] SYN-1,2-DIALKYLATED CALIX[4]ARENES - GENERAL INTERMEDIATES IN THE NAH/DMF TETRAALKYLATION OF CALIX[4]ARENES [J].

GROENEN, LC ;

RUEL, BHM ;

CASNATI, A ;

TIMMERMAN, P ;

VERBOOM, W ;

HARKEMA, S ;

POCHINI, A ;

UNGARO, R ;

REINHOUDT, DN .

TETRAHEDRON LETTERS, 1991, 32 (23) :2675-2678

[10]

Gutsche C. D, 1998, MONOGRAPHS SUPRAMOLE

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