1,3-Disubstituted p-tert-Butylcalix[4]arene Derivatives Bearing Phenanthroline Moieties: Synthesis and Selective Recognition of Silver Ion

被引:4
作者
Li, Liang [1 ]
Qi, Weiguang [2 ]
Wang, Chao [2 ]
Yan, Chaoguo [2 ]
机构
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 201418, Peoples R China
[2] 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; phenanthroline; UV spectroscopy; ion recognition; COMPLEXING PROPERTIES; FLUORESCENT SENSOR;
D O I
10.6023/cjoc201302008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
p-tert-Butylcalix[4]arene-1,3-dialdehydes were firstly obtained by two step alkylations of p-tert-butylcalix[4]arene with alkylene dihalide and hydroxyl-substituted benzaldehydes. Then p-tert-butylcalix[n]arene 1,3-disubstituted phenanthrolines were successfully prepared by condensation of active calixarene dialdehydes with 1,10-phenanthroline-5,6-dione. The structures of the prepared hoters were characterized with IR, NMR, and HRMS techniques. The recogination of calixarene 1,3-disubstituted phenanthroline for metal ions was studied with UV-Vis spectroscopy. A great affinity for Ag+ ions that can be clearly detected by naked eye was obtained.
引用
收藏
页码:1804 / 1809
页数:6
相关论文
共 21 条
[1]   Synthesis and electronic properties of series of oligothiophene-[1,10]phenanthrolines [J].
Ammann, M ;
Bäuerle, P .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (22) :4143-4152
[2]   Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications [J].
Batista, Rosa M. F. ;
Costa, Susana P. G. ;
Belsley, M. ;
Lodeiro, Carlos ;
Raposo, M. Manuela M. .
TETRAHEDRON, 2008, 64 (39) :9230-9238
[3]   Structure and binding properties of water-soluble cavitands and capsules [J].
Biros, Shannon M. ;
Rebek, Julius, Jr. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (01) :93-104
[4]   A new Hg2+-selective fluorescent sensor based on a dansyl amide-armed calix[4]-aza-crown [J].
Chen, QY ;
Chen, CF .
TETRAHEDRON LETTERS, 2005, 46 (01) :165-168
[5]   Calixarene and Calixresorcarene Glycosides: Their Synthesis and Biological Applications [J].
Dondoni, Alessandro ;
Marra, Alberto .
CHEMICAL REVIEWS, 2010, 110 (09) :4949-4977
[6]   Calixarene-based supramolecular polymerization in solution [J].
Guo, Dong-Sheng ;
Liu, Yu .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (18) :5907-5921
[7]   Ion and Molecular Recognition by Lower Rim 1,3-Di-conjugates of Calix[4]arene as Receptors [J].
Joseph, Roymon ;
Rao, Chebrolu Pulla .
CHEMICAL REVIEWS, 2011, 111 (08) :4658-4702
[8]   Calixarene-derived fluorescent probes [J].
Kim, Jong Seung ;
Quang, Duong Tuan .
CHEMICAL REVIEWS, 2007, 107 (09) :3780-3799
[9]   Synthesis of dinucleating phenanthroline-based ligands [J].
Lam, F ;
Feng, MQ ;
Chan, KS .
TETRAHEDRON, 1999, 55 (28) :8377-8384
[10]   SYNTHESIS OF ACYCLIC DINUCLEATING PHENANTHROLINE-PYRIDINE AND PHENANTHROLINE-PHOSPHINE LIGANDS [J].
LAM, F ;
CHAN, KS ;
LIU, BJ .
TETRAHEDRON LETTERS, 1995, 36 (35) :6261-6262