Characterization of a slippage stopper for the 1,2-bis(pyridinium)ethane-[24]crown-8 ether [2]pseudorotaxane motif

被引：32
作者：
Bolla, Michael A. [1 ]
Tiburcio, Jorge [1 ]
Loeb, Stephen J. [1 ]
机构：
[1] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
来源：
TETRAHEDRON | 2008年 / 64卷 / 36期
基金：
加拿大自然科学与工程研究理事会;
关键词：
D O I：
10.1016/j.tet.2008.05.042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Comparison of 1,2-bis(pyridinium)ethane axles containing iso-nicotinate esters (R=ethyl, iso-propyl, cyclohexyl, cycloheptyl) as the pyridinium unit shows that the cyclohexyl group provides a stopper size that allows slippage to be used as a method for pseudorotaxane/rotaxane formation employing dibenzo-24-crown-8 ether (DB24C8) as the wheel. Rates of complexation and decomplexation were measured in a number of solvent systems and the kinetic and thermodynamic parameters associated with the process reported. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8423 / 8427
页数：5
相关论文
共 27 条
  • [1] Clicked interlocked molecules
    Aprahamian, Ivan
    Miljanic, Ognjen S.
    Dichtel, William R.
    Isoda, Kyosuke
    Yasuda, Takuma
    Kato, Takashi
    Stoddart, J. Fraser
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2007, 80 (10) : 1856 - 1869
  • [2] THE SELF-ASSEMBLY OF [2]-ROTAXANES AND [3]-ROTAXANES BY SLIPPAGE
    ASHTON, PR
    BELOHRADSKY, M
    PHILP, D
    SPENCER, N
    STODDART, JF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (16) : 1274 - 1277
  • [3] Rotaxane or pseudorotaxane? That is the question!
    Ashton, PR
    Baxter, I
    Fyfe, MCT
    Raymo, FM
    Spencer, N
    Stoddart, JF
    White, AJP
    Williams, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) : 2297 - 2307
  • [4] *CRYSTAL IMPACT, 2008, DRAW XRAY STRUCT WER
  • [5] Wire-type ruthenium(II) complexes with terpyridine-containing [2]rotaxanes as ligands: Synthesis, characterization, and photophysical properties
    Davidson, GJE
    Loeb, SJ
    Passaniti, P
    Silvi, S
    Credi, A
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (12) : 3233 - 3242
  • [6] Channels and cavities lined with interlocked components: Metal-based polyrotaxanes that utilize pyridinimn axles and crown ether wheels as ligands
    Davidson, GJE
    Loeb, SJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) : 74 - 77
  • [7] [2]rotaxanes containing pyridinium-phosphonium axles and 24-crown-8 ether wheels
    Georges, N
    Loeb, SJ
    Tiburcio, J
    Wisner, JA
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) : 2751 - 2756
  • [8] Cooperative ion-ion interactions in the formation of interpenetrated molecules
    Hoffart, Dennis J.
    Tiburcio, Jorge
    de la Torre, Ana
    Knight, Lisa K.
    Loeb, Stephen J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 97 - 101
  • [9] Metal-organic rotaxane frameworks:: Three-dimensional polyrotaxanes from lanthanide-ion nodes, pyridinium N-oxide axles, and crown-ether wheels
    Hoffart, DJ
    Loeb, SJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) : 901 - 904
  • [10] Protecting a squaraine near-IR dye through its incorporation in a slippage-derived [2]Rotaxane
    Hsueh, Sheng-Yao
    Lai, Chien-Chen
    Liu, Yi-Hung
    Wang, Yu
    Peng, Shie-Ming
    Chiu, Sheng-Hsien
    [J]. ORGANIC LETTERS, 2007, 9 (22) : 4523 - 4526
123