Selective templated complexation of a cylindrical macrotricyclic host with neutral guests: Three cation-controlled switchable processes

被引:49
作者
Han, Tao
Chen, Chuan-Feng [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Ctr Chem Biol, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
关键词
D O I
10.1021/jo071195x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel triptycene-based cylindrical macrotricyclic host I containing an anthracene unit and two dibenzo [24]crown-8 moieties was synthesized, and its cation binding properties were studied. It was found that the host could not only form complex with the paraquat derivative 4, but also show selective templated complexation with pyromellitic diimide 2 and anthraquinone 3 in the presence of lithium and potassium ions, respectively. Consequently, two novel cascade complexes with neutral molecules as bridging species were formed in solution and in the solid state, which were structurally studied by NMR, MS spectra, and X-ray methods. Moreover, we also found that the association and dissociation of the complexes could be easily achieved by the addition and removal of lithium or potassium ions, which resulted in three cation-controlled switchable processes.
引用
收藏
页码:7287 / 7293
页数:7
相关论文
共 41 条
[1]   NOVEL BENZENE-BRIDGED MACROBICYCLIC AND MACROTRICYCLIC POLYETHERS [J].
AN, HY ;
BRADSHAW, JS ;
KRAKOWIAK, KE ;
TARBET, BJ ;
DALLEY, NK ;
KOU, XL ;
ZHU, CY ;
IZATT, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7694-7699
[2]   MACROPOLYCYCLIC POLYETHERS (CAGES) AND RELATED-COMPOUNDS [J].
AN, HY ;
BRADSHAW, JS ;
IZATT, RM .
CHEMICAL REVIEWS, 1992, 92 (04) :543-572
[3]   A molecular elevator [J].
Badjic, JD ;
Balzani, V ;
Credi, A ;
Silvi, S ;
Stoddart, JF .
SCIENCE, 2004, 303 (5665) :1845-1849
[4]   Macrocyclic aromatic ether-imide-sulfones: Versatile supramolecular receptors with extreme thermochemical and oxidative stability [J].
Colquhoun, HM ;
Williams, DJ ;
Zhu, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13346-13347
[5]  
Connors K. A., 1987, Binding Constants: The Measurement of Molecular Complex Stability
[6]  
deNamor AFD, 1996, J PHYS CHEM-US, V100, P14485
[7]   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
[8]   Small-molecule-induced folding of a synthetic polymer [J].
Ghosh, S ;
Ramakrishnan, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5441-5447
[9]  
Gloe K., 2005, MACROCYCLIC CHEM CUR
[10]   Control over charge separation in phthalocyanine-anthraquinone conjugates as a function of the aggregation status [J].
Gouloumis, Andreas ;
Gonzalez-Rodriguez, David ;
Vazquez, Purificacion ;
Torres, Tomas ;
Liu, Shenggao ;
Echegoyen, Luis ;
Ramey, Jeff ;
Hug, Gordon L. ;
Guldi, Dirk M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12674-12684