Fourfold [2]rotaxanes of calix[4]arenes by ring closure

被引:29
作者
Molokanova, Olena
Vysotsky, Myroslav O.
Cao, Yudong
Thondorf, Iris
Boehmer, Volker
机构
[1] Johannes Gutenberg Univ Mainz, Abt Lehramtskandidaten Chem, Fachbereich Chem Pharm & Geowissensch, D-55099 Mainz, Germany
[2] Univ Halle Wittenberg, Inst Biochem, Fachbereich Biochem Biotechnol, D-06099 Halle, Germany
关键词
calixarenes; hydrogen bonding; metathesis; molecular capsules; rotaxanes;
D O I
10.1002/anie.200602166
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Capsular heterodimers are formed exclusively from a tetra(tosylurea)calix[4]arene (blue) and tetrakis(3,5-dibutenyloxyphenylurea)- or tetrakis(dipentenyloxyphenylurea)calix[4]arenes (red). Metathesis between the prearranged alkenyl groups and subsequent hydrogenation leads to mechanically interlocked capsules which can neither dissociate nor release the included guest(s) owing to their fourfold [2]rotaxane structure. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8051 / 8055
页数:5
相关论文
共 42 条
[1]   Experimental and computational probes of the space in a self-assembled capsule [J].
Ajami, Dariush ;
Iwasawa, Tetsuo ;
Rebek, Julius, Jr. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (24) :8934-8936
[2]   The slipping approach to self-assembling [n]rotaxanes [J].
Asakawa, M ;
Ashton, PR ;
Ballardini, R ;
Balzani, V ;
Belohradsky, M ;
Gandolfi, MT ;
Kocian, O ;
Prodi, L ;
Raymo, FM ;
Stoddart, JF ;
Venturi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (02) :302-310
[3]   SLIPPAGE - AN ALTERNATIVE METHOD FOR ASSEMBLING [2]ROTAXANES [J].
ASHTON, PR ;
BELOHRADSKY, M ;
PHILP, D ;
STODDART, JF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (16) :1269-1274
[4]   Molecules at close range: encapsulated solvent molecules in pyrogallol[4]arene hexameric capsules [J].
Avram, L ;
Cohen, Y .
ORGANIC LETTERS, 2006, 8 (02) :219-222
[5]   A molecular elevator [J].
Badjic, JD ;
Balzani, V ;
Credi, A ;
Silvi, S ;
Stoddart, JF .
SCIENCE, 2004, 303 (5665) :1845-1849
[6]   Molecular machines [J].
Balzani, V ;
Gómez-López, M ;
Stoddart, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (07) :405-414
[7]   An atypical topoisomerase II from archaea with implications for meiotic recombination [J].
Bergerat, A ;
deMassy, B ;
Gadelle, D ;
Varoutas, PC ;
Nicolas, A ;
Forterre, P .
NATURE, 1997, 386 (6623) :414-417
[8]   Rational synthesis of multicyclic bis[2]catenanes [J].
Bogdan, A ;
Vysotsky, MO ;
Ikai, T ;
Okamoto, Y ;
Böhmer, V .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) :3324-3330
[9]   Orientational preferences of aromatic guests in dimeric capsules of tetraurea calix[4]arenes -: MD and NMR studies [J].
Broda, Frank ;
Vysotsky, Myroslav O. ;
Boehmer, Volker ;
Thondorf, Iris .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2424-2432
[10]   HOST GUEST COMPLEXATION .55. GUEST CAPTURE DURING SHELL CLOSURE [J].
BRYANT, JA ;
BLANDA, MT ;
VINCENTI, M ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2167-2172