Triply Threaded [4]Rotaxanes

被引：45
作者：
Danon, Jonathan J. [1 ]
Leigh, David A. [1 ,2 ]
McGonigal, Paul R. [2 ]
Ward, John W. [1 ]
Wu, Jhenyi [2 ]
机构：
[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England
[2] Univ Edinburgh, Sch Chem, Kings Bldg,West Mains Rd, Edinburgh EH9 3JJ, Midlothian, Scotland
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 38期
基金：
英国工程与自然科学研究理事会;
关键词：
ACTIVE-TEMPLATE SYNTHESIS; SWITCHABLE MOLECULAR SHUTTLES; ROTAXANES STABILIZATION; BLOCKING GROUP; RING; MACROCYCLES; CLICK; SIZE; STABILITY; PATHWAY;
D O I：
10.1021/jacs.6b07733
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
[4]Rotaxanes featuring three axles threaded through a single ring have been prepared through active metal template synthesis. Nickel-catalyzed sp(3)-sp(3) hornocouplings of alkyl bromide "half-threads" through 37- and 38-membered 2,2':6',2"-terpyridyl macrocycles generate triply threaded [4]rotaxanes in up to 11% yield. An analogous 39-membered macrocycle produced no rotaxane products under similar conditions. The constitutions of the [4]rotaxanes were determined by NMR spectroscopy and mass spectrometry. Doubly threaded [3]rotaxanes were also obtained from the reactions but no [2]rotaxanes were isolated, suggesting that upon demetalation the axle of a singly threaded rotaxane can slip through a macrocycle that is sufficiently large to accommodate three threads.
引用
收藏
页码：12643 / 12647
页数：5
相关论文
共 39 条
[21]   Homo- and hetero-[3]rotaxanes with two π-systems clasped in a single macrocycle [J].
Klotz, Eric J. F. ;
Claridge, Tim D. W. ;
Anderson, Harry L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (48) :15374-15375
[22]   Macrocycle Size Matters: "Small" Functionalized Rotaxanes in Excellent Yield Using the CuAAC Active Template Approach [J].
Lahlali, Hicham ;
Jobe, Kajally ;
Watkinson, Michael ;
Goldup, Stephen M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (18) :4151-4155
[23]   Template-directed synthesis of π-conjugated porphyrin [2]rotaxanes and a [4]catenane based on a six-porphyrin nanoring [J].
Langton, Matthew J. ;
Matichak, Jonathan D. ;
Thompson, Amber L. ;
Anderson, Harry L. .
CHEMICAL SCIENCE, 2011, 2 (10) :1897-1901
[24]   Hybrid organic-inorganic rotaxanes and molecular shuttles [J].
Lee, Chin-Fa ;
Leigh, David A. ;
Pritchard, Robin G. ;
Schultz, David ;
Teat, Simon J. ;
Timco, Grigore A. ;
Winpenny, Richard E. P. .
NATURE, 2009, 458 (7236) :314-318
[25]   Sequence-Specific Peptide Synthesis by an Artificial Small-Molecule Machine [J].
Lewandowski, Bartosz ;
De Bo, Guillaume ;
Ward, John W. ;
Papmeyer, Marcus ;
Kuschel, Sonja ;
Aldegunde, Maria J. ;
Gramlich, Philipp M. E. ;
Heckmann, Dominik ;
Goldup, Stephen M. ;
D'Souza, Daniel M. ;
Fernandes, Antony E. ;
Leigh, David A. .
SCIENCE, 2013, 339 (6116) :189-193
[26]   Polyyne Rotaxanes: Stabilization by Encapsulation [J].
Movsisyan, Levon D. ;
Franz, Michael ;
Hampel, Frank ;
Thompson, Amber L. ;
Tykwinski, Rik R. ;
Anderson, Harry L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (04) :1366-1376
[27]   Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction [J].
Neal, Edward A. ;
Goldup, Stephen M. .
CHEMICAL SCIENCE, 2015, 6 (04) :2398-2404
[28]   Active-template synthesis of "click" [2]rotaxane ligands: self-assembly of mechanically interlocked metallo-supramolecular dimers, macrocycles and oligomers [J].
Noor, Asif ;
Moratti, Stephen C. ;
Crowley, James D. .
CHEMICAL SCIENCE, 2014, 5 (11) :4283-4290
[29]   CuAAC "click'' active-template synthesis of functionalised [2] rotaxanes using small exo-substituted macrocycles: how small is too small? [J].
Noor, Asif ;
Lo, Warrick K. C. ;
Moratti, Stephen C. ;
Crowley, James D. .
CHEMICAL COMMUNICATIONS, 2014, 50 (53) :7044-7047
[30]   Iron(II)-templated synthesis of [3]rotaxanes by passing two threads through the same ring [J].
Prikhod'ko, Alexander I. ;
Durola, Fabien ;
Sauvage, Jean-Pierre .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :448-+
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