The quest for a molecular capsule assembled via halogen bonds

被引:56
作者
Aakeroey, Christer B. [1 ]
Rajbanshi, Arbin [1 ]
Metrangolo, Pierangelo [2 ,3 ]
Resnati, Giuseppe [2 ,3 ]
Parisi, Melchiorre F. [4 ]
Desper, John [1 ]
Pilati, Tullio [2 ]
机构
[1] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA
[2] Politecn Milan, Dept Chem Mat & Chem Engn Giulio Natta, NFMLab, I-20131 Milan, Italy
[3] IIT POLIMI, Ctr Nano Sci & Technol, I-20133 Milan, Italy
[4] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
关键词
HYDROGEN-BONDS; HETERODIMERIC CAPSULE; GUEST MOLECULES; ENCAPSULATION; RECOGNITION; CAVITIES; POLAR; DIMER;
D O I
10.1039/c2ce26173a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A halogen-bonded capsule is obtained via directed assembly of a rigid tetra(3-pyridyl) cavitand and a flexible tetra(4-iodotetra-fluorophenyl) calix[4] arene. The pyridyl nitrogen atoms from one cavitand molecule interact with the iodine atoms of a single calixarene molecule through short and directional I center dot center dot center dot N halogen bonds. The flexibility of the ethylenedioxy moieties on the calixarene platform results in positional flexibility of the iodotetrafluorobenzene sites which, coupled with a supramolecular chelating effect, allow for an effective partner-induced geometric fitting between four nitrogen atoms on the cavitand and four iodine atoms on the calixarene.
引用
收藏
页码:6366 / 6368
页数:3
相关论文
共 45 条
[1]   Hydrogen-bond driven assembly of a molecular capsule facilitated by supramolecular chelation [J].
Aakeroey, Christer B. ;
Rajbanshi, Arbin ;
Desper, John .
CHEMICAL COMMUNICATIONS, 2011, 47 (41) :11411-11413
[2]   C-pentyltetra(3-pyridyl)cavitand:: A versatile building block for the directed assembly of hydrogen-bonded heterodimeric capsules [J].
Aakeroy, Christer B. ;
Schultheiss, Nate ;
Desper, John .
ORGANIC LETTERS, 2006, 8 (12) :2607-2610
[3]   Adaptations of guest and host in expanded self-assembled capsules [J].
Ajami, Dariush ;
Rebek, Julius, Jr. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (41) :16000-16003
[4]   Multicomponent, Hydrogen-Bonded Cylindrical Capsules [J].
Ajami, Dariush ;
Rebek, Julius, Jr. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) :6584-6591
[5]   Self-recognition, structure, stability, and guest affinity of pyrogallol[4]arene and resorcin[4]arene capsules in solution [J].
Avram, L ;
Cohen, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) :11556-11563
[6]   Supramolecular rods via halogen bonding-based self-assembly of fluorinated phosphazene nanopillars [J].
Bertani, Roberta ;
Chaux, Fanny ;
Gleria, Mario ;
Metrangolo, Pierangelo ;
Milani, Roberto ;
Pilati, Tullio ;
Resnati, Giuseppe ;
Sansotera, Maurizio ;
Venzo, Alfonso .
INORGANICA CHIMICA ACTA, 2007, 360 (03) :1191-1199
[7]   Molecular recognition in methanol: The first example of hydrogen-bond-mediated self-association of a calix[4]arene in polar, protic solvent [J].
Brewster, RE ;
Shuker, SB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7902-7903
[8]   Reversible molecular capsules composed of two cavitands linked via an assortment of charged-hydrogen bonds and covalent bonds [J].
Chapman, RG ;
Sherman, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9818-9826
[9]   Selectivity in an encapsulated cycloaddition reaction [J].
Chen, J ;
Rebek, J .
ORGANIC LETTERS, 2002, 4 (03) :327-329
[10]   Self-assembling capsules [J].
Conn, MM ;
Rebek, J .
CHEMICAL REVIEWS, 1997, 97 (05) :1647-1668