Improved and Controlled Complexation of Paraquat Derivatives by the Formation of a Bis(m-phenylene)-26-Crown-8-Based Lariat Ether

被引：14

作者：

Zhang, Mingming ^{[1
]}

Luo, Yan ^{[1
]}

Zheng, Bo ^{[1
]}

Xia, Binyuan ^{[1
]}

Huang, Feihe ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 29期

基金：

中国国家自然科学基金;

关键词：

Crown compounds; Rotaxanes; Controlled assembly; Substituent effects; CROWN-ETHERS; GUEST; HOST; POLYPSEUDOROTAXANES; ORGANIZATION; CONVERSION; CRYPTAND; POLYMER; SALTS;

D O I：

10.1002/ejoc.201000926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel bis(m-phenylene)-26-crown-8-based lariat ether (i.e., 3b) was synthesized and characterized. It can bind paraquat derivatives more strongly than bis(m-plaenylene)-26-crown-8 in solution. It forms pseudorotaxanes with two paraquat derivatives in the solid state. N-Methyl substitution was found to play an important role on the binding strength of lariat ether 3b. Furthermore, due to the introduction of two benzyloxy groups, its binding to paraquat derivatives can be switched off (and back on) by adding K+ (and then dibenzo-18-crown-6), and the disassociation percentage depends on the concentration of the added K+ ions.

引用

页码：5543 / 5547

页数：5

共 41 条

[31] Complexation between pentiptycene-based mono(crown ether)s and tetracationic cyclobis(paraquat-p-phenylene): who is the host or the guest?
Cao, Jing
Lu, Hai-Yan
Xiang, Jun-Feng
Chen, Chuan-Feng
CHEMICAL COMMUNICATIONS, 2010, 46 (20) : 3586 - 3588
[32] Synthesis of poly (crown ethers)s based on bis(5-carboxy-1,3-phenylene)-26-crown-8
Nagvekar, DS
Gibson, HW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 106 - POLY
[33] Pseudocryptand-Type [3]Pseudorotaxane and "Hook-Ring" Polypseudo[2]catenane Based on a Bis(m-phenylene)-32-crown-10 Derivative and Bisparaquat Derivatives
Niu, Zhenbin
Slebodnick, Carla
Gibson, Harry W.
ORGANIC LETTERS, 2011, 13 (17) : 4616 - 4619
[34] COMPLEXATION THERMODYNAMICS OF IMINE-TYPE BIS(BENZOCROWN ETHER)S .1. SANDWICH COMPLEXATION OF K+, RB+, CS+ AND TL+ WITH POLYMETHYLENE AND M-PHENYLENE BRIDGED CARBONYLHYDRAZONES OF 4'-FORMYLBENZO-15-CROWN-5
GRUTTNER, C
HOLDT, HJ
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1993, 16 (03): : 219 - 230
[35] A novel fluorescence sensor for K+ based on bis-Bodipy: The ACQ, effect controlled by cation complexation of pseudo crown ether ring
Yan, Zhenxi
Lin, Xiaoru
Guo, Hongyu
Yang, Fafu
TETRAHEDRON LETTERS, 2017, 58 (31) : 3064 - 3068
[36] The First [2]Pseudorotaxane and the First Pseudocryptand-Type Poly[2]pseudorotaxane Based on Bis(meta-phenylene)-32-Crown-10 and Paraquat Derivatives
Niu, Zhenbin
Slebodnick, Carla
Bonrad, Klaus
Huang, Feihe
Gibson, Harry W.
ORGANIC LETTERS, 2011, 13 (11) : 2872 - 2875
[37] Pseudocryptand-Type [3]Pseudorotaxane and "Hook-Ring" Polypseudo[2]catenane Based on a Bis(m-phenylene)-32-crown-10 Derivative and Bisparaquat Derivatives (vol 13, pg 4616, 2011)
Niu, Zhenbin
Slebodnick, Carla
Gibson, Harry W.
ORGANIC LETTERS, 2011, 13 (19) : 5410 - 5410
[38] Pseudocryptand-Type [2]Pseudorotaxanes Based on Bis(meta-phenylene)-32-Crown-10 Derivatives and Paraquats with Remarkably Improved Association Constants
Niu, Zhenbin
Slebodnick, Carla
Schoonover, Daniel
Azurmendi, Hugo
Harich, Kim
Gibson, Harry W.
ORGANIC LETTERS, 2011, 13 (15) : 3992 - 3995
[39] MACROCYCLIC POLYMERS .2. SYNTHESIS OF POLY(AMIDE CROWN ETHER)S BASED ON BIS(5-CARBOXY-1,3-PHENYLENE)-32-CROWN-10 - NETWORK FORMATION THROUGH THREADING
DELAVIZ, Y
GIBSON, HW
MACROMOLECULES, 1992, 25 (19) : 4859 - 4862
[40] The First [2]Pseudorotaxane and the First Pseudocryptand-Type Poly[2]pseudorotaxane Based on Bis(meta-phenylene)-32-Crown-10 and Paraquat Derivatives (vol 13, pg 2872, 2011)
Niu, Zhenbin
Slebodnick, Carla
Bonrad, Klaus
Huang, Feihe
Gibson, Harry W.
ORGANIC LETTERS, 2011, 13 (19) : 5411 - 5411

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