Synthesis of A Bis-Macrotricyclic Host and Its Complexation with Secondary Ammonium Salts: An Acid-Base Switchable Molecular Handcuff

被引：11

作者：

Guo, Jia-Bin ^{[1
,2
]}

Xiang, Jun-Feng ^{[1
]}

Chen, Chuan-Feng ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 26期

基金：

中国国家自然科学基金;

关键词：

Self-assembly; Structure elucidation; Host-guest systems; Macrocycles; BIS(CROWN ETHER) HOST; DRIVEN; IONS; COOPERATIVITY; MULTIVALENCY; DERIVATIVES; POLYETHERS; CHEMISTRY; POLYMER; BINDING;

D O I：

10.1002/ejoc.201000675

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel triptycene-derived bis-macrotricyclic host was designed and synthesized. The host was shown to form a 1:4 stable complex with 4 equiv. of dibenzylammonium salt in solution and in the solid state. Moreover, it was found that the host with multicavities could also self-assemble with 2 equiv. of bis-secondary ammonium salt to form a handcuff-like structure under the tested condition ([1](0) = 3.0 mM). The complexation and decomplexation of the assembly could be further chemically controlled by the stimuli of acid and base.

引用

收藏

页码：5056 / 5062

页数：7

相关论文

共 46 条

[1] MACROPOLYCYCLIC POLYETHERS (CAGES) AND RELATED-COMPOUNDS [J].

AN, HY ;

BRADSHAW, JS ;

IZATT, RM .

CHEMICAL REVIEWS, 1992, 92 (04) :543-572

[2] CATENATED CYCLODEXTRINS [J].

ARMSPACH, D ;

ASHTON, PR ;

BALLARDINI, R ;

BALZANI, V ;

GODI, A ;

MOORE, CP ;

PRODI, L ;

SPENCER, N ;

STODDART, JF ;

TOLLEY, MS ;

WEAR, TJ ;

WILLIAMS, DJ .

CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (01) :33-55

[3] A molecular elevator [J].

Badjic, JD ;

Balzani, V ;

Credi, A ;

Silvi, S ;

Stoddart, JF .

SCIENCE, 2004, 303 (5665) :1845-1849

[4] Multivalency and cooperativity in supramolecular chemistry [J].

Badjic, JD ;

Nelson, A ;

Cantrill, SJ ;

Turnbull, WB ;

Stoddart, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (09) :723-732

[5] 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

[6] 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

[7] The exclusivity of multivalency in dynamic covalent processes [J].

Badjic, JD ;

Cantrill, SJ ;

Grubbs, RH ;

Guidry, EN ;

Orenes, R ;

Stoddart, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3273-3278

[8] Cooperativity in the self-assembly of porphyrin ladders [J].

Camara-Campos, A ;

Hunter, CA ;

Tomas, S .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (09) :3034-3038

[9] Self-assembly of disk-shaped molecules to coiled-coil aggregates with tunable helicity [J].

Engelkamp, H ;

Middelbeek, S ;

Nolte, RJM .

SCIENCE, 1999, 284 (5415) :785-788

[10] LINEAR MOLECULAR RECOGNITION - SPECTROSCOPIC, PHOTOPHYSICAL, AND COMPLEXATION STUDIES ON ALPHA,OMEGA-ALKANEDIYLDIAMMONIUM IONS BINDING TO A BISANTHRACENYL MACROTRICYCLIC RECEPTOR [J].

FAGES, F ;

DESVERGNE, JP ;

KAMPKE, K ;

BOUASLAURENT, H ;

LEHN, JM ;

MEYER, M ;

ALBRECHTGARY, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3658-3664

← 1 2 3 4 5 →