Templated hierarchical self-assembly of poly(p-aryltriazole) foldamers.

A biomimetic approach has been used for the templated self-assembly of a helical poly(para-aryltriazole) foldamer. The solvophobic folding process yields helices that further self-assemble into long nanotubes (see picture; scale bar: 100 nm). Constructs of controlled length and chirality can be generated by applying a poly(γ-benzyl-l-glutamate) scaffold at the appropriate assembly conditions, mimicking tobacco mosaic virus self-assembly.

[1]  I. Huc,et al.  Identification of a foldaxane kinetic byproduct during guest-induced single to double helix conversion. , 2012, Journal of the American Chemical Society.

[2]  Jun-Li Hou,et al.  Aromatic amide foldamers: structures, properties, and functions. , 2012, Chemical reviews.

[3]  S. Hecht,et al.  Optically active, amphiphilic poly(meta-phenylene ethynylene)s: synthesis, hydrogen-bonding enforced helix stability, and direct AFM observation of their helical structures. , 2012, Journal of the American Chemical Society.

[4]  Hua Jiang,et al.  Template-induced screw motions within an aromatic amide foldamer double helix. , 2011, Angewandte Chemie.

[5]  A. Grélard,et al.  Helix-Rod Host-Guest Complexes with Shuttling Rates Much Faster than Disassembly , 2011, Science.

[6]  J. Leger,et al.  Relative helix-helix conformations in branched aromatic oligoamide foldamers. , 2011, Journal of the American Chemical Society.

[7]  S. Hecht,et al.  Designing structural motifs for clickamers: exploiting the 1,2,3-triazole moiety to generate conformationally restricted molecular architectures. , 2011, Chemistry.

[8]  Amar H Flood,et al.  Flipping the switch on chloride concentrations with a light-active foldamer. , 2010, Journal of the American Chemical Society.

[9]  Didier Dubreuil,et al.  Diastereoselective encapsulation of tartaric acid by a helical aromatic oligoamide. , 2010, Journal of the American Chemical Society.

[10]  Kyu-Sung Jeong,et al.  Foldamers with helical cavities for binding complementary guests. , 2009, Chemical Society reviews.

[11]  Fuyi Wang,et al.  Folding and aggregation of cationic oligo(aryl-triazole)s in aqueous solution. , 2009, Chemistry.

[12]  Zhan-Ting Li,et al.  Intramolecular Six-Membered and Three-Center C-H···O Hydrogen Bonding in 1,4-Diphenyl-1,2,3-Triazoles , 2009 .

[13]  A. Flood,et al.  Strong, size-selective, and electronically tunable C-H...halide binding with steric control over aggregation from synthetically modular, shape-persistent [34]triazolophanes. , 2008, Journal of the American Chemical Society.

[14]  Stefan Hecht,et al.  Helicity inversion in responsive foldamers induced by achiral halide ion guests. , 2008, Angewandte Chemie.

[15]  S. Hecht,et al.  Helixinversion in responsiven Foldameren durch achirale Gastmoleküle (Halogenidionen) , 2008 .

[16]  B. Gong,et al.  Hollow crescents, helices, and macrocycles from enforced folding and folding-assisted macrocyclization. , 2008, Accounts of chemical research.

[17]  J. Lenhardt,et al.  1,2,3-Triazole CH...Cl(-) contacts guide anion binding and concomitant folding in 1,4-diaryl triazole oligomers. , 2008, Angewandte Chemie.

[18]  A. Flood,et al.  Pure C-H hydrogen bonding to chloride ions: a preorganized and rigid macrocyclic receptor. , 2008, Angewandte Chemie.

[19]  Ronald A. Smaldone,et al.  Reactive sieving with foldamers: inspiration from nature and directions for the future. , 2008, Chemistry.

[20]  J. Lehn,et al.  Naphthyridine-based helical foldamers and macrocycles: synthesis, cation binding, and supramolecular assemblies. , 2008, The Journal of organic chemistry.

[21]  Jeffrey S. Moore,et al.  Foldamers Based on Solvophobic Effects , 2007 .

[22]  Scott J. Shandler,et al.  Foldamers as versatile frameworks for the design and evolution of function. , 2007, Nature chemical biology.

[23]  A. Spek,et al.  "Click" 1,2,3-triazoles as tunable ligands for late transition metal complexes. , 2007, Dalton transactions.

[24]  M. Wasielewski,et al.  Solution-phase structure of an artificial foldamer: X-ray scattering study. , 2007, Journal of the American Chemical Society.

[25]  M. Inouye,et al.  Helix formation in synthetic polymers by hydrogen bonding with native saccharides in protic media. , 2006, Chemistry.

[26]  Aaron Klug Vom Makromolekül zum biologischen Molekülverband (Nobel‐Vortrag) , 2006 .

[27]  Indrajit Ray,et al.  VTrust: A Trust Management System Based on a Vector Model of Trust , 2005, ICISS.

[28]  M. Laguerre,et al.  Solution structure of quinoline- and pyridine-derived oligoamide foldamers. , 2005, Chemistry.

[29]  E. W. Meijer,et al.  Facile synthesis of a chiral polymeric helix; folding by intramolecular hydrogen bonding. , 2004, Chemical communications.

[30]  J. Saven,et al.  Simulation Studies of a Helical m-Phenylene Ethynylene Foldamer , 2004 .

[31]  Matthew T. Stone,et al.  Helical pitch of m-phenylene ethynylene foldamers by double spin labeling. , 2002, Journal of the American Chemical Society.

[32]  David J. Hill,et al.  Helicogenicity of solvents in the conformational equilibrium of oligo(m-phenylene ethynylene)s: Implications for foldamer research , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[33]  Matthew J. Mio,et al.  A field guide to foldamers. , 2001, Chemical reviews.

[34]  Sébastien Lecommandoux,et al.  Self-Assembly of Rod−Coil Diblock Oligomers Based on α-Helical Peptides , 2001 .

[35]  E. W. Meijer,et al.  Cooperativity in the folding of helical m-phenylene ethynylene oligomers based upon the 'sergeants-and-soldiers' principle. , 2001, Chemistry.

[36]  E. W. Meijer,et al.  Self-assembly of folded m-phenylene ethynylene oligomers into helical columns. , 2001, Journal of the American Chemical Society.

[37]  Berl,et al.  Template-induced and molecular recognition directed hierarchical generation of supramolecular assemblies from molecular strands , 2000, Chemistry.

[38]  J. Homo,et al.  Encoded Helical Self‐Organization and Self‐Assembly into Helical Fibers of an Oligoheterocyclic Pyridine – Pyridazine Molecular Strand , 2000 .

[39]  Moore,et al.  Twist Sense Bias Induced by Chiral Side Chains in Helically Folded Oligomers. , 2000, Angewandte Chemie.

[40]  A. Klug The tobacco mosaic virus particle: structure and assembly. , 1999, Philosophical transactions of the Royal Society of London. Series B, Biological sciences.

[41]  Jeffery G. Saven,et al.  Cooperative Conformational Transitions in Phenylene Ethynylene Oligomers: Chain-Length Dependence , 1999 .

[42]  J. Rebek,et al.  The 55 % Solution: A Formula for Molecular Recognition in the Liquid State , 1998 .

[43]  J S Moore,et al.  Solvophobically driven folding of nonbiological oligomers. , 1997, Science.

[44]  G. Whitesides,et al.  Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures. , 1991, Science.

[45]  Jonathan S. Lindsey,et al.  Self-Assembly in Synthetic Routes to Molecular Devices. Biological Principles and Chemical Perspectives: A Review , 1991 .

[46]  Aaron Klug,et al.  From Macromolecules to Biological Assemblies (Nobel Lecture) , 1983 .

[47]  T. S. Hughes,et al.  Foldamers as dynamic receptors: probing the mechanism of molecular association between helical oligomers and rodlike ligands. , 2002, Angewandte Chemie.