Synthesis of rotacatenanes by the combination of Cu-mediated threading reaction and the template method: the dual role of one ligand

被引:33
作者
Hayashi, Ryuto [1 ]
Wakatsuki, Kota [1 ]
Yamasaki, Ryu [1 ]
Mutoh, Yuichiro [1 ]
Kasama, Takeshi [2 ]
Saito, Shinichi [1 ]
机构
[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan
[2] Tokyo Med & Dent Univ, Res Ctr Med & Dent Sci, Bunkyo Ku, Tokyo 1138510, Japan
关键词
DIRECTED SYNTHESIS; RING SIZE; MOLECULAR SHUTTLES; BLOCKING GROUP; ROTAXANES; CATENANES; MACROCYCLE; STABILITY; ION;
D O I
10.1039/c3cc47425a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rotacatenanes were synthesized by the catalytic reaction using a macrocyclic phenanthroline-CuI complex followed by the installation of another ring by the template method. In this approach, the size of the ring component of the rotaxane turns out to be a very important factor for the synthesis of rotacatenanes.
引用
收藏
页码:204 / 206
页数:3
相关论文
共 56 条
[1]   Interlocked and intertwined structures and superstructures [J].
Amabilino, DB ;
Stoddart, JF .
CHEMICAL REVIEWS, 1995, 95 (08) :2725-2828
[2]  
Amabilino DB, 1999, EUR J ORG CHEM, V1999, P1295
[3]  
Anderson S., 1996, ANGEW CHEM INT EDIT, V35, P1956
[4]   Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures [J].
Aucagne, V ;
Hänni, KD ;
Leigh, DA ;
Lusby, PJ ;
Walker, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2186-2187
[5]   Catalytic "Active-Metal" template synthesis of [2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the Cu(I)-catalyzed azide-alkyne 1,3-cycloaddition [J].
Aucagne, Vincent ;
Berna, Jose ;
Crowley, James D. ;
Goldup, Stephen M. ;
Haenni, Kevin D. ;
Leigh, David A. ;
Lusby, Paul J. ;
Ronaldson, Vicki E. ;
Slawin, Alexandra M. Z. ;
Viterisi, Aurlien ;
Walker, D. Barney .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11950-11963
[6]   A Multistate Switchable [3]Rotacatenane [J].
Barin, Gokhan ;
Coskun, All ;
Friedman, Douglas C. ;
Olson, Mark A. ;
Colvin, Michael T. ;
Carmielli, Raanan ;
Dey, Sanjeev K. ;
Bozdemir, O. Altan ;
Wasielewski, Michael R. ;
Stoddart, J. Fraser .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) :213-222
[7]   Positive Cooperativity in the Template-Directed Synthesis of Monodisperse Macromolecules [J].
Belowich, Matthew E. ;
Valente, Cory ;
Smaldone, Ronald A. ;
Friedman, Douglas C. ;
Thiel, Johannes ;
Cronin, Leroy ;
Stoddart, J. Fraser .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5243-5261
[8]   Cadiot-Chodkiewicz active template synthesis of rotaxanes and switchable molecular shuttles with weak intercomponent interactions [J].
Berna, Jose ;
Goldup, Stephen M. ;
Lee, Ai-Lan ;
Leigh, David A. ;
Symes, Mark D. ;
Teobaldi, Gilberto ;
Zerbetto, Francesco .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) :4392-4396
[9]   A catalytic palladium active-metal template pathway to [2]rotaxanes [J].
Berna, Jose ;
Crowley, James D. ;
Goldup, Stephen M. ;
Haenni, Kevin D. ;
Lee, Ai-Lan ;
Leigh, David A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) :5709-5713
[10]   Strategies and Tactics for the Metal-Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links [J].
Beves, Jonathon E. ;
Blight, Barry A. ;
Campbell, Christopher J. ;
Leigh, David A. ;
McBurney, Roy T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9260-9327