Acid/base controllable molecular switch based on a neutral phenanthroline guest penetrated pseudorotaxane.

A ditopic macrocycle with a bisamide and a half dibenzo-crown ether component has been newly synthesized and its complexation behavior toward neutral phenanthroline derivatives is reported. The macrocycle can bind phenanthroline derivatives very strongly by hydrogen bonding and pi-electron interaction, yielding pseudorotaxane structures. The inclusion complexes show a pH controllable reversible threading-dethreading molecular switching system.

[1]  H. Gibson,et al.  Supramacromolecular Chemistry: Self-Assembly of Polystyrene-Based Multi-Armed Pseudorotaxane Star Polymers from Multi-Topic C60 Derivatives , 2010 .

[2]  T. Takata,et al.  Selective transformation of a crown ether/sec-ammonium salt-type rotaxane to N-alkylated rotaxanes. , 2010, Organic letters.

[3]  H. Tian,et al.  Bright functional rotaxanes. , 2010, Chemical Society reviews.

[4]  Feihe Huang,et al.  Complexes of Diquat with Dibenzo-24-Crown-8 , 2009 .

[5]  Minjae Lee,et al.  Synthesis of Complementary Host- and Guest-Functionalized Polymeric Building Blocks and Their Self-Assembling Behavior , 2009 .

[6]  Feihe Huang,et al.  Supramacromolecular self-assembly: Chain extension, star and block polymers via pseudorotaxane formation from well-defined end-functionalized polymers , 2009 .

[7]  Jason J. Davis,et al.  Interlocked host rotaxane and catenane structures for sensing charged guest species via optical and electrochemical methodologies. , 2009, Organic & biomolecular chemistry.

[8]  H. Gibson,et al.  High-yielding, regiospecific synthesis of cis(4,4')-di(carbomethoxybenzo)-30-crown-10, its conversion to a pyridyl cryptand and strong complexation of 2,2'- and 4,4'-bipyridinium derivatives. , 2008, The Journal of organic chemistry.

[9]  K. Fujiwara,et al.  Entropy- and hydrolytic-driven positional switching of macrocycle between imine- and hydrogen-bonding stations in rotaxane-based molecular shuttles. , 2008, Journal of the American Chemical Society.

[10]  Feihe Huang,et al.  A new functional bis(m-phenylene)-32-crown-10-based cryptand host for paraquats. , 2008, The Journal of organic chemistry.

[11]  T. Takata,et al.  Crown ether–tert-ammonium salt complex fixed as rotaxane and its derivation to nonionic rotaxane , 2008 .

[12]  Yi‐Hung Liu,et al.  A [2]rotaxane-based (1)H NMR spectroscopic probe for the simultaneous identification of physiologically important metal ions in solution. , 2007, Chemical communications.

[13]  Yi‐Hung Liu,et al.  Using acetate anions to induce translational isomerization in a neutral urea-based molecular switch. , 2007, Angewandte Chemie.

[14]  Feihe Huang,et al.  Competitive interactions of two ion-paired salts with a neutral host to form two non-ion-paired complexes. , 2007, The Journal of organic chemistry.

[15]  Feihe Huang,et al.  Formation of a Linear Supramolecular Polymer by Self-Assembly of Two Homoditopic Monomers Based on the Bis(m-phenylene)-32-crown-10/Paraquat Recognition Motif , 2007 .

[16]  S. W. Thomas,et al.  Chemical sensors based on amplifying fluorescent conjugated polymers. , 2007, Chemical reviews.

[17]  Francesco Zerbetto,et al.  Synthetic molecular motors and mechanical machines. , 2007, Angewandte Chemie.

[18]  M. W. Hosseini,et al.  Molecular tectonics: generation of 1-D interdigitated and 2-D interwoven helical silver coordination networks by oligoethylene glycol based tectons bearing two benzonitrile moieties , 2007 .

[19]  Michinori Karikomi,et al.  Chiral sensing for amino acid derivative based on a [2]rotaxane composed of an asymmetric rotor and an asymmetric axle. , 2006, Chemical communications.

[20]  Bao-hang Han,et al.  Cyclodextrin rotaxanes and polyrotaxanes. , 2006, Chemical reviews.

[21]  Feihe Huang,et al.  [3]Pseudorotaxanes based on the cryptand/monopyridinium salt recognition motif , 2005 .

[22]  Bradley F. Habenicht,et al.  Regioselective routes to disubstituted dibenzo crown ethers and their complexations. , 2005, Organic & biomolecular chemistry.

[23]  P. Beer,et al.  Anion directed synthesis of a hydrogensulfate selective luminescent rotaxane. , 2005, Chemical communications.

[24]  T. Aida,et al.  Toward intelligent molecular machines: directed motions of biological and artificial molecules and assemblies. , 2005, Chemical reviews.

[25]  Emiko Koyama,et al.  [3]rotaxane synthesized via covalent bond formation can recognize cations forming a sandwich structure. , 2005, Chemical communications.

[26]  T. Takata,et al.  Synthesis of novel interlocked systems utilizing a palladium complex with 2,6-pyridinedicarboxamide-based tridentate macrocyclic ligand , 2004 .

[27]  Y. Nagawa,et al.  Synthesis of [1]rotaxane via covalent bond formation and its unique fluorescent response by energy transfer in the presence of lithium ion. , 2004, Journal of the American Chemical Society.

[28]  P. Beer,et al.  Halide anion directed assembly of luminescent pseudorotaxanes. , 2004, Chemical communications.

[29]  T. Takata,et al.  Asymmetric benzoin condensation catalyzed by chiral rotaxanes tethering a thiazolium salt moiety via the cooperation of the component: can rotaxane be an effective reaction field? , 2004, Journal of the American Chemical Society.

[30]  Alan E. Rowan,et al.  Epoxidation of polybutadiene by a topologically linked catalyst , 2003, Nature.

[31]  H. Gibson,et al.  Ion pairing and host-guest complexation in low dielectric constant solvents. , 2003, Journal of the American Chemical Society.

[32]  Vincenzo Balzani,et al.  Molecular Devices and Machines– A Journey into the Nano World , 2003 .

[33]  P. Beer,et al.  Anion-templated rotaxane formation. , 2002, Journal of the American Chemical Society.

[34]  Keiji Hirose A Practical Guide for the Determination of Binding Constants , 2001 .

[35]  Stoddart,et al.  Artificial Molecular Machines. , 2000, Angewandte Chemie.

[36]  TakataToshikazu,et al.  Rotaxanes Functionalized by Chirality: Novel Rotaxanes Consisting of Binaphthol-Based Chiral Crown Ether , 2000 .

[37]  Bradley D. Smith,et al.  A Macrobicyclic Receptor with Versatile Recognition Properties: Simultaneous Binding of an Ion Pair and Selective Complexation of Dimethylsulfoxide , 2000 .

[38]  T. Swager,et al.  Conjugated polymer-based chemical sensors. , 2000, Chemical reviews.

[39]  Mason,et al.  A New Cryptand: Synthesis and Complexation with Paraquat. , 1999, Organic letters.

[40]  Bradley D. Smith,et al.  [2]Rotaxane with a cation-binding wheel , 2000 .

[41]  Laurence Raehm,et al.  A Transition Metal Containing Rotaxane in Motion: Electrochemically Induced Pirouetting of the Ring on the Threaded Dumbbell , 1999 .

[42]  Jean-Pierre Sauvage,et al.  Complete rearrangement of a multi-porphyrinic rotaxane by metallation–demetallation of the central coordination site , 1998 .

[43]  David A. Leigh,et al.  Peptide-Based Molecular Shuttles , 1997 .

[44]  H. Gibson,et al.  DIFUNCTIONAL DERIVATIVES OF BIS(M-PHENYLENE)-32-CROWN-10 , 1997 .

[45]  David J. Williams,et al.  Pseudorotaxanes Formed Between Secondary Dialkylammonium Salts and Crown Ethers , 1996 .

[46]  Pablo Gaviña,et al.  Electrochemically induced molecular motions in a copper(I) complex pseudorotaxane , 1996 .

[47]  David J. Williams,et al.  Dialkylammonium Ion/Crown Ether Complexes: The Forerunners of a New Family of Interlocked Molecules , 1995 .

[48]  Douglas Philp,et al.  A new design strategy for the self-assembly of molecular shuttles , 1992 .