Complexation of a Pentiptycene-Based Tweezer-Like Receptor with Paraquat Derivatives: Ion-Controlled Binding and Release of the Guests

被引：29

作者：

Cao, Jing ^{[1
,2
]}

Lu, Hai-Yan ^{[2
]}

You, Xiao-Jun ^{[1
]}

Zheng, Qi-Yu ^{[1
]}

Chen, Chuan-Feng

机构：

[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 19期

基金：

中国国家自然科学基金;

关键词：

MOLECULAR TWEEZER; MACROTRICYCLIC HOST; SALTS; DENDRIMERS; CORE;

D O I：

10.1021/ol901805y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new tweezer-like receptor containing a pentiptycene unit and a benzene ring linked by two crown ether chains has been synthesized. It could form stable complexes with paraquat derivatives with different functional groups in solution and in the solid state. It was found that the complexes dissociated upon two one-electron reduction of the bipyridinium ring. Moreover, binding and release of the guest molecules could also be easily controlled by the addition and removal of potassium ion.

引用

页码：4446 / 4449

页数：4

共 31 条

[1] Prototype of an optically responsive molecular switch based on pseudorotaxane [J].

Asakawa, M ;

Iqbal, S ;

Stoddart, JF ;

Tinker, ND .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (09) :976-978

[2] Host-guest complexes between an aromatic molecular tweezer and symmetric and unsymmetric dendrimers with a 4,4′-bipyridinium core [J].

Balzani, V ;

Bandmann, H ;

Ceroni, P ;

Giansante, C ;

Hahn, U ;

Klämer, FG ;

Müller, U ;

Müller, WM ;

Verhaelen, C ;

Vicinelli, V ;

Vögtle, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :637-648

[3] Tweezering the core of a dendrimer:: A photophysical and electrochemical study [J].

Balzani, V ;

Ceroni, P ;

Giansante, C ;

Vicinelli, V ;

Klärner, FG ;

Verhaelen, C ;

Vögtle, F ;

Hahn, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) :4574-4578

[4] Synthesis, structures, and properties of peripheral o-dimethoxy-substituted pentiptycene quinones and their o-quinone derivatives [J].

Cao, Jing ;

Lu, Hai-Yan ;

Chen, Chuan-Feng .

TETRAHEDRON, 2009, 65 (39) :8104-8112

[5] A pentiptycene-based bis(crown ether) host: synthesis and its complexation with cyclobis(paraquat-p-phenylene) [J].

Cao, Jing ;

Jiang, Yi ;

Zhao, Jian-Min ;

Chen, Chuan-Feng .

CHEMICAL COMMUNICATIONS, 2009, (15) :1987-1989

[6] Dendrimers with a 4,4′-bipyridinium core and electron-donor branches.: Electrochemical and spectroscopic properties [J].

Ceroni, P ;

Vicinelli, V ;

Maestri, M ;

Balzani, V ;

Müller, WM ;

Müller, U ;

Hahn, U ;

Osswald, F ;

Vögtle, F .

NEW JOURNAL OF CHEMISTRY, 2001, 25 (08) :989-993

[7]

Connors K. A., 1987, Binding Constants: The Measurement of Molecular Complex Stability

[8] A triptycene-based bis(crown ether) host: Complexation with both paraquat derivatives and dibenzylammonium salts [J].

Han, T ;

Chen, CF .

ORGANIC LETTERS, 2006, 8 (06) :1069-1072

[9] Complexation of triptycene-based cylindrical macrotricyclic polyether toward diquaternary salts: Ion-controlled binding and release of the guests [J].

Han, Tao ;

Zong, Qian-Shou ;

Chen, Chuan-Feng .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) :3108-3111

[10] Chiral molecular tweezers [J].

Harmata, M .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (11) :862-873

← 1 2 3 4 →