Synthesis, recognition of metal ions of salicylidenimine functionalized p-tert-butylcalix[n]arene-core dendrimers

被引:7
作者
Wang, Yunyan [1 ]
Cai, Yahua [1 ]
Yan, Chaoguo [1 ]
机构
[1] Yangzhou Univ, Coll chem & Chem Engn, Yangzhou 225002, Peoples R China
基金
中国国家自然科学基金;
关键词
calixarene; dendrimer; extraction; Schiff base; complexation; ion recognition; CALIXARENE-BASED DENDRIMERS; RECEPTORS;
D O I
10.1080/10610270601124001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of salicylidenimine functionalized p-tert-butylcalix[n]arene-core dendrimers 7a-b were synthesized in higher yields by divergent method from the corresponding ethyl p-butylcalix[n]arylacetates 2a-b (n = 6, 8). 2a-b were first treated with excess of 1,6-diaminohexane to give amide derivatives with free amine terminal groups 3a-b, which in turn reacted with salicylaldehyde in alcohol to yield the first generation of Schiff bases 4a-b. 3a-b reacted with ethyl acrylate, ammonolized with 1,6-diaminohexane and condonsated with salicylaldehyde successfully to give the second generation of Schiff bases 7a-b. The extraction and binding properties of the dentritic Schiff bases 4a-b and 7a-b for several kinds of metal ions were studied with UV-Vis spectroscopy and atomic absorption spectroscopy. In which they showed a great affinity for soft Cu2+ ions and formed 1:1 or 1:2 stoichiometric complexes.
引用
收藏
页码:467 / 473
页数:7
相关论文
共 35 条
[1]   Novel chiral (salen)MnIII complexes containing a calix[4]arene unit as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes [J].
Amato, ME ;
Ballistreri, FP ;
Pappalardo, A ;
Tomaselli, GA ;
Toscano, RM ;
Williams, DJ .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (16) :3562-3570
[2]   Calixarene-based dendrimers. A timely review [J].
Baklouti, L ;
Cheriaa, N ;
Mahouachi, M ;
Abidi, R ;
Kim, JS ;
Kim, Y ;
Vicens, J .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2006, 54 (1-2) :1-7
[3]   CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].
BOHMER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745
[4]   The synthesis of calix[4]crown based dendrimer [J].
Bu, JH ;
Zheng, QY ;
Chen, CF ;
Huang, ZT .
TETRAHEDRON, 2005, 61 (04) :897-902
[5]   Calixarene-based dendrimers. Second generation of a calix[4]-dendrimer with a 'tren' as core [J].
Cheriaa, N ;
Abidi, R ;
Vicens, J .
TETRAHEDRON LETTERS, 2005, 46 (09) :1533-1536
[6]   Hyperbranched molecules based on calixarenes [J].
Cheriaa, N ;
Abidi, R ;
Vicens, J .
TETRAHEDRON LETTERS, 2004, 45 (41) :7795-7799
[7]   A new approach to dendrimers made from p-tert-butyl calix[4]arenes [J].
Cheriaa, Najah ;
Mahouach, Mouna ;
Ben Othman, Amel ;
Baklouti, Lassaad ;
Kim, Yang ;
Abidi, Rym ;
Vicens, Jacques .
SUPRAMOLECULAR CHEMISTRY, 2006, 18 (03) :265-271
[8]   An organometallic octopus complex: Structure and properties of a resorcinarene with 16 cobalt centers [J].
Eisler, D ;
Hong, W ;
Jennings, MC ;
Puddephatt, RJ .
ORGANOMETALLICS, 2002, 21 (19) :3955-3960
[9]  
FRANCOISE AN, 1989, J AM CHEM SOC, V111, P8681
[10]  
Ge Y, 2004, CHEM J CHINESE U, V25, P1836