Counterion-induced translational isomerism in a bistable [2]rotaxane.

Translational isomerization can be induced by changing the anions associated with a bistable rotaxane in which the tetracationic cyclophane (blue box), cyclobis(paraquat-p-phenylene), encircles a dumbbell component containing bispyrrolotetrathiafulvalene (green) and a dioxynaphthalene (red) recognition sites. The rotaxane was isolated as both its hexafluorophosphate and tris(tetrachlorobenzenediolato)phosphate(v) (TRISPHAT(-)) salts. Photophysical measurements and NMR spectroscopy carried out in acetone (CD(3)COCD(3)) and acetonitrile (CD(3)CN) solutions reveal that the much larger TRISPHAT(-) anion favors predominantly the encirclement of the green site by the blue box.

[1]  G. Bernardinelli,et al.  Synthesis and Resolution of the Configurationally Stable Tris(tetrachlorobenzenediolato)phosphate(V) Ion , 1997 .

[2]  Stoddart,et al.  Switching of pseudorotaxanes and catenanes incorporating a tetrathiafulvalene unit by redox and chemical inputs , 2000, The Journal of organic chemistry.

[3]  R. J. Abraham,et al.  NMR, solvation and theoretical investigations of conformational isomerism in 2‐X‐cyclohexanones (X=NMe2, OMe, SMe and SeMe) , 2003 .

[4]  Hsian-Rong Tseng,et al.  Switchable neutral bistable rotaxanes. , 2004, Journal of the American Chemical Society.

[5]  Douglas Philp,et al.  The Control of Translational Isomerism in Catenated Structures. , 1994 .

[6]  G. Bernardinelli,et al.  Crystal packing interpretation of the association of chiral threefold propeller ions: TRISPHAT anion with a triarylcarbenium cation , 2002 .

[7]  J. Lacour,et al.  Application of TRISPHAT anion as NMR chiral shift reagent , 1997 .

[8]  Xiang Zhang,et al.  The metastability of an electrochemically controlled nanoscale machine on gold surfaces. , 2004, Chemphyschem : a European journal of chemical physics and physical chemistry.

[9]  William A. Goddard,et al.  Meccano on the Nanoscale—A Blueprint for Making Some of the World's Tiniest Machines , 2004 .

[10]  Vincenzo Balzani,et al.  Redox-controllable amphiphilic [2]rotaxanes. , 2004, Chemistry.

[11]  Tohru Yamamoto,et al.  Langmuir and Langmuir-Blodgett films of amphiphilic bistable rotaxanes. , 2004, Langmuir : the ACS journal of surfaces and colloids.

[12]  Tohru Yamamoto,et al.  Two-dimensional molecular electronics circuits. , 2002, Chemphyschem : a European journal of chemical physics and physical chemistry.

[13]  Hsian-Rong Tseng,et al.  Toward chemically controlled nanoscale molecular machinery. , 2003, Angewandte Chemie.

[14]  David A Leigh,et al.  Shuttling through anion recognition. , 2004, Angewandte Chemie.

[15]  Hsian-Rong Tseng,et al.  Molecular shuttles based on tetrathiafulvalene units and 1,5-dioxynaphthalene ring systems. , 2004, Chemistry.

[16]  W. Vetter,et al.  Synthesis, Isolation, and Identification of Translationally Isomeric [3]Catenanes , 1981 .

[17]  J. F. Stoddart,et al.  Redox-induced ring shuttling and evidence for folded structures in long and flexible two-station rotaxanes , 2003 .

[18]  Jan Becher,et al.  Poised on the brink between a bistable complex and a compound. , 2002, Organic letters.

[19]  Hsian-Rong Tseng,et al.  Single-walled carbon nanotube based molecular switch tunnel junctions. , 2003, Chemphyschem : a European journal of chemical physics and physical chemistry.

[20]  Stoddart,et al.  Self-assembly of an amphiphilic , 2000, Organic letters.

[21]  J. Lacour,et al.  Simple Ion Exchange Procedure of Common Anions to TRISPHAT. Application to the Purification of Cationic Species , 1998 .

[22]  J. Fraser Stoddart,et al.  Slow shuttling in an amphiphilic bistable [2]rotaxane incorporating a tetrathiafulvalene unit , 2001 .

[23]  J Fraser Stoddart,et al.  In the twilight zone between [2]pseudorotaxanes and [2]rotaxanes. , 2003, Chemistry.

[24]  J. Fraser Stoddart,et al.  Amphiphilic Bistable Rotaxanes , 2003 .

[25]  Atsushi Ikeda,et al.  Novel Cavity Design Using Calix[n]arene Skeletons: Toward Molecular Recognition and Metal Binding. , 1997, Chemical reviews.