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
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
[31]   Synthetic molecular motors and mechanical machines [J].
Kay, Euan R. ;
Leigh, David A. ;
Zerbetto, Francesco .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :72-191
[32]   SUPRAMOLECULAR CHEMISTRY - SCOPE AND PERSPECTIVES MOLECULES, SUPERMOLECULES, AND MOLECULAR DEVICES [J].
LEHN, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1988, 27 (01) :89-112
[33]   CRYPTATES - CHEMISTRY OF MACROPOLYCYCLIC INCLUSION COMPLEXES [J].
LEHN, JM .
ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (02) :49-57
[34]   Precise facial control in threading guests into a molecular cage and the formation of a turtlelike supramolecular complex [J].
Lin, Chi-Feng ;
Liu, Yi-Hung ;
Lai, Chien-Chen ;
Peng, Shie-Ming ;
Chiu, Sheng-Hsien .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3176-3181
[35]   Template-directed synthesis employing reversible imine bond formation [J].
Meyer, Cari D. ;
Joiner, C. Steven ;
Stoddart, J. Fraser .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (11) :1705-1723
[36]   CYCLIC POLYETHERS AND THEIR COMPLEXES WITH METAL SALTS [J].
PEDERSEN, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (26) :7017-&
[37]   Mono-, bis-, and tris(crown ether)s assembled around 1,3,5-triaroylbenzene scaffolds [J].
Pigge, F. Christopher ;
Dighe, Mayuri K. ;
Houtman, Jon C. D. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2760-2767
[38]  
Schrader T, 2005, FUNCTIONAL SYNTHETIC RECEPTORS, P1, DOI 10.1002/352760572X
[39]  
Steed J.W., 2009, SUPRAMOL CHEM, VSecond
[40]   Optically sensed, molecular shuttles driven by acid-base chemistry [J].
Vella, Sarah J. ;
Tiburcio, Jorge ;
Loeb, Stephen J. .
CHEMICAL COMMUNICATIONS, 2007, (45) :4752-4754