Template-directed synthesis of mechanically interlocked molecular bundles using dynamic covalent chemistry

被引:79
作者
Northrop, Brian H.
Arico, Fabio
Tangchiavang, Nick
Badjic, Jovica D.
Stoddart, J. Fraser
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[2] Univ Calif Los Angeles, Calif NanoSyst Inst, Los Angeles, CA 90095 USA
关键词
D O I
10.1021/ol061262u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mixing the dipyrido[24] crown-8 derivatives carrying one or two formyl group(s) on the 4 position(s) of their pyridine ring(s) with a 3symmetrical trisammonium ion template in a 3: 1 ratio in CD3NO2 results in the formation of thermodynamically stable [4] which, upon addition of a 1,3,5-trisaminobenzene cap, form mechanically interlocked molecular bundles with one and two caps, by virtue of dynamic imine bond formation.
引用
收藏
页码:3899 / 3902
页数:4
相关论文
共 83 条
[1]   Knot tied around an octahedral metal centre [J].
Adams, H ;
Ashworth, E ;
Breault, GA ;
Guo, J ;
Hunter, CA ;
Mayers, PC .
NATURE, 2001, 411 (6839) :763-763
[2]   EXPANDING ROLES FOR TEMPLATES IN SYNTHESIS [J].
ANDERSON, S ;
ANDERSON, HL ;
SANDERS, JKM .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (09) :469-475
[3]   Long-range electron transfer in porphyrin-containing [2]-rotaxanes:: Tuning the rate by metal cation coordination [J].
Andersson, M ;
Linke, M ;
Chambron, JC ;
Davidsson, J ;
Heitz, V ;
Hammarström, L ;
Sauvage, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4347-4362
[4]   Template-directed synthesis of multiply mechanically interlocked molecules under thermodynamic control [J].
Aricó, F ;
Chang, T ;
Cantrill, SJ ;
Khan, SI ;
Stoddart, JF .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (16) :4655-4666
[5]   Switching "on" and "off" the expression of chirality in peptide rotaxanes [J].
Asakawa, M ;
Brancato, G ;
Fanti, M ;
Leigh, DA ;
Shimizu, T ;
Slawin, AMZ ;
Wong, JKY ;
Zerbetto, F ;
Zhang, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2939-2950
[6]  
Ashton PR, 1997, LIEBIGS ANN-RECL, P2485
[7]   A molecular elevator [J].
Badjic, JD ;
Balzani, V ;
Credi, A ;
Silvi, S ;
Stoddart, JF .
SCIENCE, 2004, 303 (5665) :1845-1849
[8]   Operating molecular elevators [J].
Badjic, JD ;
Ronconi, CM ;
Stoddart, JF ;
Balzani, V ;
Silvi, S ;
Credi, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1489-1499
[9]   A mechanically interlocked bundle [J].
Badjic, JD ;
Balzani, V ;
Credi, A ;
Lowe, JN ;
Silvi, S ;
Stoddart, JF .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) :1926-1935
[10]   α- and β-cyclodextrin rotaxanes of μ-bis(4-pyridyl)bis[pentacyanoferrate(II)] complexes [J].
Baer, AJ ;
Macartney, DH .
INORGANIC CHEMISTRY, 2000, 39 (07) :1410-1417