Supramolecular Chemistry : Concepts and Perspectives

 Content: VOLUME 1: CONCEPTS Contributors to Volume 1 xiii Foreword xv Preface xvii Abbreviations and Acronyms xix Concepts 1 Definition and Emergence of Supramolecular Chemistry 3 Jonathan W. Steed/Jerry L. Atwood/Philip A. Gale Supramolecular Interactions 9 Dushyant B. Varshey/John R. G. Sander/Tomislav Friscic/ Leonard R. MacGillivray Complementarity and Preorganization 25 James B. Wittenberg/Lyle Isaacs The Thermodynamics of Molecular Recognition 45 Corinne L. D. Gibb/Bruce C. Gibb Cooperativity and the Chelate, Macrocyclic and Cryptate Effects 67 Richard W. Taylor/Rowshan Ara Begum/Victor W. Day/Kristin Bowman-James Multivalency 95 Mary J. Cloninger/BaCsar BilgiCcer/Lingyin Li/Shane L. Mangold/Scott T. Phillips/Mark L. Wolfenden Solvation Effects in Supramolecular Recognition 117 Mikhail Rekharsky/Yoshihisa Inoue Competition Experiments 135 Lei You/Eric V. Anslyn Supramolecular Information/Programming from a Boolean Perspective 161 A. Prasanna de Silva Self-Assembly and Self-Organization 167 Michael F. Geer/Linda S. Shimizu Introduction to Surfactant Self-Assembly 181 Laurence S. Romsted Reversible Covalent Bond Toolbox 205 Yunfeng Cheng/Hanjing Peng/Binghe Wang Chirality 217 F. Richard Keene VOLUME 2: TECHNIQUES Contributors to Volume 2 xiii Foreword xvii Preface xix Abbreviations and Acronyms xxi Techniques 237 Binding Constants and Their Measurement 239 Pall Thordarson Isothermal Titration Calorimetry in Supramolecular Chemistry 275 Franz P. Schmidtchen NMR Spectroscopy in Solution 297 Jesus Garcia/Lucas G. Martins/Miquel Pons Diffusion Ordered NMR Spectroscopy (DOSY) 319 Alceo Macchioni/Gianluca Ciancaleoni/Cristiano Zuccaccia/Daniele Zuccaccia Solid-State NMR Studies on Supramolecular Chemistry 331 Michele R. Chierotti/Roberto Gobetto Mass Spectrometry and Gas-Phase Chemistry of Supermolecules: A Primer 347 Egor V. Dzyuba/Johannes Poppenberg/Sebastian Richter/Ralf W. Troff/Christoph A. Schalley Luminescent Spectroscopy in Supramolecular Chemistry 379 Sundus Erbas-Cakmak/Ruslan Guliyev/Engin U. Akkaya Circular Dichroism Spectroscopy 393 Tohru Taniguchi/Toyonobu Usuki Dynamic Light Scattering in Supramolecular Materials Chemistry 411 Jorg Braun/Kasper Renggli/Julia Razumovitch/Corinne Vebert X-Ray Diffraction: Addressing Structural Complexity in Supramolecular Chemistry 425 Gary D. Enright/Satoshi Takeya/John A. Ripmeester Small-Angle X-ray Scattering (SAXS) and Wide-Angle X-ray Scattering (WAXS) of Supramolecular Assemblies 437 Adriana C. Toma/Thomas Pfohl Supramolecular Electrochemistry 451 Amar H. Flood/Angel E. Kaifer Transport Experiments in Membranes 473 Stefan Matile/Naomi Sakai/Andreas Hennig Vesicles in Supramolecular Chemistry 501 Bart Jan Ravoo Rheology 517 Christophe Chassenieux/Laurent Bouteiller Langmuir-Blodgett Films 529 Jeremy J. Ramsden Affinity Capillary Electrophoresis as a Tool to Characterize Intermolecular Interactions 543 Steffen Kiessig/Alexandra Stettler/Samuel Fuhrimann/Maria Anna Schwarz Ion Chromatography and Membrane Separations Using Macrocyclic Ligands 563 John D. Lamb/Na Li Brewster Angle Microscopy 589 Keith J. Stine Scanning Electron Microscopy 619 Zhan-Ting Li/Xin Zhao Transmission Electron Microscopy (TEM) 633 Jun-ichi Kikuchi/Kazuma Yasuhara Scanning Tunneling Microscopy (STM) 647 Meike Stohr Atomic Force Microscopy (AFM) 659 Janne T. Hyotyla/Roderick Y. H. Lim Scanning Near-Field Optical Microscopy (SNOM) 669 Gerd Kaupp Computational Techniques (DFT, MM, TD-DFT, PCM) 689 Rosemary Sheehan/Peter J. Cragg Uses of Differential Sensing and Arrays in Chemical Analysis 709 Michelle M. Adams/Leo A. Joyce/Eric V. Anslyn VOLUME 3: MOLECULAR RECOGNITION Contributors to Volume 3 xiii Foreword xv Preface xvii Abbreviations and Acronyms xix Molecular Recognition 731 Crown and Lariat Ethers 733 Peter J. Cragg/Rafik Vahora Azacycloalkanes and Azacyclophanes 753 Antonio Bianchi/Enrique Garcia-Espa"na Hetero-Crown Ethers-Synthesis and Metal-Binding Properties of Macrocyclic Ligands Bearing Group 16 (S, Se, Te) Donor Atoms 785 William Levason/Gillian Reid Cryptands and Spherands 811 Leonard F. Lindoy/Ki-Min Park/Shim Sung Lee Schiff Base and Reduced Schiff Base Ligands 827 Bellam Sreenivasulu Calixarenes in Molecular Recognition 863 Laura Baldini/Francesco Sansone/Alessandro Casnati/Rocco Ungaro Cyclotriveratrylene and Cryptophanes 895 Michaele J. Hardie Carcerands and Hemicarcerands 917 Ralf Warmuth Cyclodextrins: From Nature to Nanotechnology 955 Stephen F. Lincoln/Duc-Truc Pham Cucurbituril Receptors and Drug Delivery 983 Anthony Ivan Day/J. Grant Collins Podands 1001 Adam N. Swinburne/Jonathan W. Steed Porphyrins and Expanded Porphyrins as Receptors 1045 Jonathan L. Sessler/Elizabeth Karnas/Elaine Sedenberg Supramolecular Phthalocyanine-Based Systems 1075 Christian G. Claessens/M. Victoria Martinez-Diaz/Tomas Torres Guanidinium-Based Receptors for Oxoanions 1101 Matthew P. Conley/Julian Valero/Javier de Mendoza Anion Receptors Containing Heterocyclic Rings 1125 Philip A. Gale/Cally J. E. Haynes Amide and Urea-Based Receptors 1153 Md. Alamgir Hossain/Rowshan Ara Begum/Victor W. Day/Kristin Bowman-James Synthetic Peptide-Based Receptors 1179 Stefan Kubik Biological Small Molecules as Receptors 1205 Carolina Godoy-Alc'antar/Anatoly K. Yatsimirsky Receptors for Nucleotides 1225 Enrique Garc'ia-Espana/Raquel Belda/Jorge Gonzalez/Javier Pitarch/Antonio Bianchi Receptors for Zwitterionic Species 1259 Santiago V. Luis/Ignacio Alfonso/Francisco Galindo Ion-Pair Receptors 1281 Antonella Dalla Cort Metal Complexes as Receptors 1309 Stephen J. Loeb Hydrogen-Bonding Receptors for Molecular Guests 1325 Andrew J. Wilson Boronic Acid-Based Receptors 1345 John S. Fossey/Tony D. James VOLUME 4: SUPRAMOLECULAR CATALYSIS, REACTIVITY AND CHEMICAL BIOLOGY Contributors to Volume 4 xiii Foreword xvii Preface xix Abbreviations and Acronyms xxi Supramolecular Reactivity 1381 Supramolecular Organocatalysis 1383 Philip A. Woods/Andrew D. Smith Replication Processes-From Autocatalysis to Systems Chemistry 1415 J..urgen Huck/Douglas Philp Artificial Enzyme Mimics 1447 Barbara Geibel/Michael Merschky/Carolin Rether/Carsten Schmuck Dynamic Covalent Chemistry 1497 Giulio Gasparini/Marta Dal Molin/Andrea Lovato/Leonard J. Prins Reaction Networks 1527 Zehavit Dadon/Nathaniel Wagner/Rivka Cohen-Luria/Gonen Ashkenasy Reactions in Dynamic Self-Assemblies 1543 E. Moulin/N. Giuseppone Reactivity in Nanoscale Vessels 1575 Boris Breiner/Jonathan R. Nitschke Reactions in Solid-State Inclusion Compounds 1589 Kenneth D.M. Harris/Benjamin A. Palmer/Gregory R. Edwards-Gau Functional Polymers 1613 David Chappell/Barnaby W. Greenland/Wayne Hayes Supramolecular Aspects of Chemical Biology 1637 Rational Design of Peptide-Based Biosupramolecular Systems 1639 Aimee L. Boyle/Derek N. Woolfson Nucleic Acid Mimetics 1665 Matthew B. Coppock/Mary Elizabeth Williams Supramolecular Approaches to the Study of Glycobiology 1685 Thisbe K. Lindhorst/Stefan Kubik Porphyrinoids: Highly Versatile, Redox-Active Scaffolds for Supramolecular Design and Biomimetic Applications 1713 Jonathan P. Hill/Francis D'Souza/Katsuhiko Ariga Supramolecular Chemistry of Membranes 1731 Gavin T. Noble/Robert J. Mart/Kwan Ping Liem/Simon J. Webb Membrane Transport 1751 Roberto Quesada Supramolecular Bioinorganic Chemistry 1771 Jean-Noel Rebilly/Olivia Reinaud The Role of Supramolecular Chemistry in Responsive Vectors for Gene Delivery 1807 Caroline M. LaManna/Mark W. Grinstaff Supramolecular Chemistry in In Vitro Biosensors 1825 Jing Sun/Min Cai/John J. Lavigne Supramolecular Chemistry in Biological Imaging In Vivo 1851 Elise A. Schultz-Sikma/Thomas J. Meade Aptamer Moieties in Biochemical Applications 1877 Michael J. Donovan/Ling Meng/Basri Gulbakan/Yan Chen/Parag Parekh/Kwame Sefah/Weihong Tan Supramolecular Approaches for Inhibition of Protein-Protein and Protein-DNA Interactions 1885 Cooper H. Battle/Janarthanan Jayawickramarajah Supramolecular Approaches to Medicinal Chemistry 1909 Shannon Biros/Fraser Hof Supramolecular Systems for Tissue Engineering 1929 Adinarayana Andukuri/Jeremy B. Vines/Joel M. Anderson/Ho-Wook Jun Chemical Biology Using Fluorinated Building Blocks 1947 Cristina Y. Zamora/Laila Dafik/Krishna Kumar VOLUME 5: SELF-ASSEMBLY AND SUPRAMOLECULAR DEVICES Contributors to Volume 5 xiii Foreword xvii Preface xix Abbreviations and Acronyms xxi Self-Processes 1965 Template Strategies in Self-Assembly 1967 David B. Amabilino Self-Assembly of Coordination Compounds: Design Principles 1993 Santiago Alvarez/Eliseo Ruiz Self-Assembly of Coordination Chains and Helices 2045 Inhar Imaz/Daniel Maspoch Self-Assembly of Coordination Cages and Spheres 2071 Sota Sato/Takashi Murase/Makoto Fujita Self-Assembly of Organic Supramolecular Capsules 2085 Alessandro Scarso/Giuseppe Borsato Self-Assembly of Supramolecular Wires 2115 Jean Weiss/Matthieu Koepf/Jennifer A. Wytko Synthesis of Supramolecular Nanotubes 2149 Rebeca Garc'ia-Fandi"no/Manuel Amor'in/Juan R. Granja Organic Foldamers and Helices 2183 Ivan Huc/Hua Jiang Self-Assembly of Macromolecular Threaded Systems 2207 Yuya Tachibana/Kazuko Nakazono/Toshikazu Takata Self-Assembled Links: Catenanes 2225 Nicholas H. Evans/Paul D. Beer Templated Synthesis of Knots and Ravels 2245 Jean-Pierre Sauvage/David B. Amabilino Self-Assembly of Nucleic Acids 2263 Karina M. M. Carneiro/Pik Kwan Lo/Hanadi F. Sleiman Viruses as Self-Assembled Templates 2275 Jennifer M. Rego/Hyunmin Yi Peptide Self-Assembly 2293 Silvia Cavalli/Hana Robson Marsden/Fernando Albericio/Alexander Kros Rotaxanes-Self-Assembled Links 2311 Xiang Ma/He Tian Supramolecular Devices 2331 Photoprocesses of Relevance to Supramolecular Chemistry 2333 Fabian Spanig/Alexandre Haefele/Felix N. Castellano Photoinduced Electron Transfer Processes in Biological and Artificial Supramolecules 2365 Mamoru Fujitsuka/Tetsuro Majima Molecular Devices: Energy Transfer 2397 Sara Bonacchi/Damiano Genovese/Riccardo Juris/Marco Montalti/Luca Prodi/Enrico Rampazzo/Nelsi Zaccheroni Molecular Devices: Molecular Machinery 2425 Mingming Zhang/Kelong Zhu/Feihe Huang Molecular Logic Gates 2497 A. Prasanna de Silva Single-Molecule Electronics 2507 Robert M. Metzger Molecular Redox Sensors 2523 James H. R. Tucker Ion-Selective Electrodes With Ionophore-Doped Sensing Membranes 2539 Philippe Buhlmann/Li D. Chen Colorimetric Sensors 2581 Hiromitsu Maeda/Pavel Anzenbacher, Jr Luminescent Sensing 2611 Jonathan A. Kitchen/Raman Parkesh/Emma B. Veale/Thorfinnur Gunnlaugsson Photoswitching Materials 2643 Chi-Chiu Ko/Vivian Wing-Wah Yam Supramolecular Chemistry in Medicine 2675 Stephen Faulkner/Alan M. Kenwright Magnetic Resonance Imaging Contrast Agents 2693 Celia S. Bonnet/Eva Toth Supramolecular Chemistry for Organic Photovoltaics 2725 Pavel A. Troshin/Niyazi S. Sariciftci VOLUME 6: SUPRAMOLECULAR MATERIALS CHEMISTRY Contributors to Volume 6 xiii Foreword xv Preface xvii Abbreviations and Acronyms xix Supramolecular Materials Chemistry 2789 Crystal Engineering 2791 Edward R. T. Tiekink Noncovalent Interactions in Crystals 2829 Paola Gilli/Gastone Gilli Concepts and Nomenclature in Chemical Crystallography 2869 Leonard J. Barbour/Dinabandhu Das/Tia Jacobs/Gareth O. Lloyd/Vincent J. Smith Crystal Structure Prediction 2905 Graeme M. Day The Cambridge Structural Database System and Its Applications in Supramolecular Chemistry and Materials Design 2927 Elna Pidcock/James A. Chisholm/Peter A. Wood/Peter T.A. Galek/Laszlo Fabian/Oliver Korb/Aurora J. Cruz-Cabeza/John W. Liebeschuetz/Colin R. Groom/Frank H. Allen Crystal Growth and Molecular Crystal Growth Modification 2947 Franca Jones/Mark I. Ogden Polymorphism: Fundamentals and Applications 2957 Srinivasulu Aitipamula/Ashwini Nangia Cocrystals: Synthesis, Structure, and Applications 2975 Christer B. Aakeroy/Prashant D. Chopade Mechanical Preparation of Crystalline Materials. An Oxymoron? 2993 Dario Braga/Elena Dichiarante/Fabrizia Grepioni/Giulio I. Lampronti/Lucia Maini/Paolo P. Mazzeo/Simone D'Agostino Physico-Chemical Aspects of Inclusion Compounds 3009 Nikoletta B. Bathori/Luigi R. Nassimbeni Clathrate Hydrates 3017 Saman Alavi/Konstantin Udachin/Christopher I. Ratcliffe/John A. Ripmeester Synthetic Clathrate Systems 3033 Roger Bishop Network and Graph Set Analysis 3057 Lars R. Ohrstrom Coordination Polymers 3073 Edwin C. Constable Zeolitelike Metal-Organic Frameworks (ZMOFs): Design, Structure, and Properties 3087 Mohamed H. Alkordi/Mohamed Eddaoudi Interpenetration 3107 Stuart R. Batten Supramolecular Isomerism 3121 Susan A. Bourne Gas Storage and Separation in Supramolecular Materials 3133 Jian Tian/Praveen K. Thallapally/Bernard Peter McGrail Templated [2 + 2] Photodimerizations in the Solid State 3153 Elizabeth Elacqua/Rebecca C. Laird/Leonard R. MacGillivray VOLUME 7: SOFT MATTER Contributors to Volume 7 xiii Foreword xv Preface xvii Abbreviations and Acronyms xix Soft Matter 3167 Soft Matter Science-a Historical Overview with a Supramolecular Perspective 3169 David K. Smith Multicomponent Self-Assembled Polymers Based on pi-Conjugated Systems 3183 Adrien Kaeser/Martin Wolffs/Albertus P. H. J. Schenning Functions Based on Dynamic Structural Changes of Coordination Polymers 3205 Mitsuru Kondo Self-Healing and Mendable Supramolecular Polymers 3221 Stefano Burattini/Howard M. Colquhoun/Barnaby W. Greenland/Wayne Hayes Assembly of Block Copolymers 3235 Dave J. Adams/Paul D. Topham Molecularly Imprinted Polymers 3255 Borje Sellergren/Andrew J. Hall Supramolecular Dendrimer Chemistry 3283 Monica Soler/George R. Newkome Hyperbranched Polymers in Supramolecular Chemistry 3297 Barnaby W. Greenland/Wayne Hayes Supramolecular Chemistry in Polymer Networks 3321 Pol Besenius/Peter A. G. Cormack Stimuli-Responsive and Motile Supramolecular Soft Materials 3337 Paul D. Topham/Anthony J. Ryan Self-Assembling Fibrillar Networks-Supramolecular Gels 3355 David K. Smith Self-Assembly of Facial Amphiphiles in Water 3377 Job Boekhoven/Patrick van Rijn/Jan H. van Esch Self-Assembly of Surfactants at Solid Surfaces 3395 Michele Ferrari Physisorption for Self-Assembly of Supramolecular Systems: A Scanning Tunneling Microscopy Perspective 3419 Kunal S. Mali/Jinne Adisoejoso/Inge De Cat/Tanya Balandina/Elke Ghijsens/Zongxia Guo/Min Li/Mahesh Sankara Pillai/Willem Vanderlinden/Hong Xu/Steven De Feyter Chemisorbed Self-Assembled Monolayers 3445 Omar Azzaroni/Roberto C. Salvarezza Self-Organization and Self-Assembly in Liquid-Crystalline Materials 3463 John W. Goodby/Isabel M. Saez/Stephen J. Cowling Liquid Crystals Formed from Specific Supramolecular Interactions 3493 Duncan W. Bruce Covalent Capture of Self-Assembled Soft Materials 3515 Bing Gong Designing Peptide-Based Supramolecular Biomaterials 3525 Vineetha Jayawarna/Rein V. Ulijn Self-Assembly of Polymers into Soft Nanoparticles and Nanocapsules 3541 Jianbin Tang/Dingcheng Zhu/Youqing Shen Self-Assembled Polymer Supermolecules as Templates for Nanomaterials 3563 Bhanu Nandan/Manfred Stamm VOLUME 8: NANOTECHNOLOGY Contributors to Volume 8 xiii Foreword xv Preface xvii Abbreviations and Acronyms xix Nanotechnology 3587 Nanotechnology: The "Top-Down" and "Bottom-Up" Approaches 3589 Parvez Iqbal/Jon A. Preece/Paula M. Mendes Nanolithography 3603 Graham J. Leggett Two-Dimensional Supramolecular Chemistry 3625 Anna G. Phillips/Peter H. Beton/Neil R. Champness Biologically Derived Supramolecular Materials 3647 Steven J. Langford/Melissa J. Latter/Bradley E. Wilman/Sheshanath V. Bhosale Supramolecular Hybrid Nanomaterials as Prospective Sensing Platforms 3669 Mustafa Biyikal/Mandy Hecht/Ramon Martinez-Manez/Knut Rurack/Felix Sancenon Self-Assembled Nanoparticles 3699 Dr Rachel K. O'Reilly Photochemically Driven Molecular Devices and Machines 3719 Alberto Credi/Serena Silvi/Margherita Venturi Magnetically Responsive Self-Assembled Composite Materials 3751 Alshakim Nelson/Qiu Dai Advances in Supramolecular Chemistry of Carbon Nanotubes 3767 Gregg P. Kotchey/Alexander Star One-Dimensional Nanostructures of Molecular Graphenes 3791 Wei Zhang/Takanori Fukushima/Takuzo Aida Supramolecular Nanoparticles for Molecular Diagnostics and Therapeutics 3809 Kuan-Ju Chen/Mitch Andre Garcia/Hao Wang/Hsian-Rong Tseng Atomic Force Microscopy Measurements of Supramolecular Interactions 3825 Bo Song/Holger Schonherr Nanoelectronics 3841 Nathan D. McClenaghan/Aurelien Ducrot Glossary 3859 Subject Index 3887