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Calixarenes: An Introduction de C. David Gutsche

Calixarenes: An Introduction: Monographs in Supramolecular Chemistry

Autor C. David Gutsche
en Limba Engleză Hardback – 29 feb 2008
Calixarenes belong to a family of macrocyclic compounds based on a hydrozyalkylation product of a phenol and an aldehyde, and are probably the world's most readily available synthetic molecular basket. The word calixarene is derived from calyx, Greek for chalice and arene in reference to the presence of aryl groups in the cyclic array. Calixarenes are appealing subjects for research since they can be functionalized in myriad ways to provide interesting and useful materials. As a result of their ease of synthesis they have attracted worldwide attention. Calixarenes An Introduction provides a concise overview of the field with particular attention to the historical development of Calixarenes. Topics covered include how to synthesize and functionalize Calixarenes, examination of Calixarenes properties and applied uses of Calixarenes. The volume contains extensive references to recent literature, offering the reader a valid presentation of information, and will be of immediate value to researchers, as well as graduates and professionals, who require a comprehensive introduction to the subject.
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Specificații

ISBN-13: 9780854042586
ISBN-10: 085404258X
Pagini: 276
Dimensiuni: 155 x 234 x 23 mm
Greutate: 0.59 kg
Ediția:Nouă
Editura: Royal Society Of Chemistry
Seria Monographs in Supramolecular Chemistry

Locul publicării:United Kingdom

Cuprins

Chapter 1: From Resinous Tar to Molecular Basket; 1.1: The Resinous Tar; 1,2: Glistening Crystals: The Zinke Products; 1,3: More Crystals: The Niederl Products; 1.4: Cyclic Tetramers: Proofs of Structure; 1.5: The Petrolite Chapter; 1.6: Cyclic Tetramers and the Quest for Enzyme Mimics; 1.7: Unraveling the Literature; 1.8: Nomenclature and Representation of the Calixarenes; Chapter 2: Making the Baskets: Synthesis of Calixarenes; 2.1: One-step, Base-Induced Syntheses of Phenol-derived Calixarenes; 2.1.1: Synthesis of p-tert-Butylcalixarenes; 2.1.2: Synthesis of Other p-Substituted Calixarenes; 2.2: One-step, Acid-catalyzed Synthesis of Calixarenes; 2.2.1: Phenol-derived Calixarenes; 2.2.2: Resorcinol-derived Calixarenes; 2.3: Multi-step Synthesis of Calixarenes; 2.3.1: Non-convergent Stepwse syntheses; 2.3.2: Convergent Stepwise Syntheses (Fragment Condensation Procedure); 2.4: Synthesis of Calixarene-related Compounds; 2.4.1: Norcalixarenes and Homocalixarenes; 2.4.2: Oxacalixarenes, Azacalixarenes, and Thiacalixarenes; 2.4.3: Homooxacalixarenes and Homoazacalixarenes; 2.4.4: Heterocalixarenes; 2.5: Mechanism of Calixarene-forming Reactions; 2.5.1: Mechanism of the Base-induced Reactioin; 2.5.2: Mechanism of the Acid-catalyzed Reaction; 2.6: Concluding Remarks; Chapter 3 Proving the Baskets: The Characterization and Properties of Calixarenes; 3.1: Separation and Purfiication of Calixarenes; 3.2: X-Ray Crystallography: The Ultimate Proof of Structure 3.3: Physical Properties of Calixarenes; 3.3.1 : Melting Points; 3.3.2: Solubilities; 3.3.3: pKa Values; 3.4: Dipole Moments of Calixarenes; 3.5: Spectral Properties of Calixarenes; 3.5.1: Infrared Spectra; 3.5.2: Ultraviolet Spectra; 3.5.3: NMR Spectra; 3.5.4: Mass Spectra; 3.6: Concluding Remarks; Chapter 4: Shaping the Baskets: Conformations of Calixarenes; 4.1: Conformational Representation and Nomenclature; 4.2: Computationl studies of Calixarene Conformations; 4.3: Conformations of Calixarenes in the Solid State; 4.3.1: Calix[4]arenes; 4.3.2: Calix[5]arenes; 4.3.3: Calix[6]arenes; 4.3.4: Calix[7]arenes; 4.3.5: Calix[8]arenes; 4.3.6: Large Calixarenes; 4.4: Conformations of Flexible Calixarenes in Solution; 4.4.1: Conformational Mobility of Calix[n]arenes; 4.4.1.1: Conformations of Calix[4]arenes; 4.4.1.2: Conformational Mobility of Calixarenes Lager than Calix[4]arenes; 4.4.1.3: Conformational Mobility of Oxacalixarenes and Azacalixarenes; 4.4.1.4: Conformational Mobility of Calixresorcarenes and C-Substituted Calixarenes; 4.4.1.5: Conformational Mobility of Thiacalixarenes; 4.4.1.6: Conformational Mobility of Calixarene Ethers, Deoxycalixarenes, Calixaquinones and Calixarenetiols; 4.4.2: Pathways for Cone-cone Interconvesion of Calix[4]arenes; 4.5: Conformationally Immobile Calixarenes; 4.5.1: Minimum Structural Requirements for Conformational Immobility of Unbridged Calixarene Ethers and Esters; 4.5.1.1: Identification of Fixed Conformers; 4.5.1.2: Fully Etherified and Esterified Calixarenes; 4.5.1.3: Partially Etherified and Esterified Calixarenes; 4.5 1.4: Meta-substituted Calixarenes; 4.5.2: Conformational Immobilization via Bridging; 4.5.3: Conformational Freezing via Oxygen-Metal Bridges; 4.6: Factors Governing the Conformational Outcome of Derivitazation; 4.6.1: O-Tetrasubstitution of Calix[4]arenes; 4.6.2: Mono-, Di- and Tri-O-substitution of Calix[4]arenes; 4.6.3: O-Substitution of Calix[5]arenes and Calix[6]arenes; 4.6.4: Calixarene Oxyanions; 4.6.4.1: Calix[4]arene Oxyanions; 4.6.4.2: Calix[6]arene Oxyanions; 4.7: Chiral Calixarenes; 4.8: Concluding Remarks; Chapter 5: Embroidering the Baskets: Introduction of Functional Groups; 5.1: Functionalization Involving the OH Groups; 5.1.1: Esterfication; 5.1.2: Etherification; 5.1.2.1: With Simple Alkyl Halides; 5.1.2.2: With Functionalized Alkylating Agents; 5.1.3: Endo Rim-bridged Calixarenes; 5.1.4: Replacement of OH with H, N and S; 5.2: Modifying the Exo Rim of Calixarenes; 5.2.1: General Overview; 5.2.2: Halogenation, Nitratin, Sulfonation and Diazonium Coupling Reactions; 5.2.3: Alkylation (including Chloromethylation) Route; 5.2.4: Acylation and Aroylation Routes; 5.2.5: Arylation Reactions; 5.2.6: Aminomethyation: The p-Quinonemethide Route; 5.2.7: p-Claisen Rearrangement Route; 5.3: Functionalization of the Methylene Bridges; 5.4: Exo Rim-Bridged Calixarenes; 5.5: Oxidation of Calixarenes; 5.5.1: Calixquinones; 5.5.2: Spirodienones; 5.6: Reduction of Calixarenes; 5.7: Selective Functionalizaton; 5.8: Concluding Remarks; Chapter 6 : Combining the Baskets: Multi-Calixarenes; 6.1: Calixarenes Intermolecularly Bridged by Covalent Bonding; 6.1.1: Bridging the Endo Rims, 6.1.2: Bridging the Exo Rims; 6.1.3: Multi-Calxarenes and Calixarene Dendrimers; 6.2: Calixarenes Intermolecular Bridged by Non-covalent Bonding; 6.2.1: Dimeric Assemblies of Calixarenes; 6.2.2: Catenanes and Rotaxanes; 6.2.3: Oligomeric and Polymeric Assemblies of Calixarenes; 6.2.4: Callllixarenes in Monolayers and Interrrfaces; 6.3: Calixarene Polymers; 6.4: Concluding Remarks; Chapter 7: Filling the Baskets: Complex Formation with Calixarenes; 7.1: Solid State Complexes; 7.2: Solution State Complexes of Metal Cations with Endo Rim-substituted Calixarenes; 7.2.1: Complexation with Parent Calixarenes; 7.2.2: Complexation with Endo Rim-substituted Calixarenes; 7.2.1.1: Endo Rim Ethers; 7.2.1.2: Endo Rim Esters; 7.2.1.3: Endo Rim Ketones; 7.2.1.4 Endo Rim Amides; 7.2.1.5: Endo Rim Carboxylic Acids; 7.2.1.6: Endo Rim Phosphorus- and Sulfur-containing Groups; 7.2.1.7: Nitrogen-containing Chelating Groups on Endo Rim; 7.2.3: Calixcrowns; 7.2.4: Calixspherands; 7.3: Solution State Complexes of Metal Cations with Exo Rim-substituted Calixarenes; 7.4: Anion Complexes with Calixarenes; 7.5: Salt Complexes with Calixarenes; 7.6: Solution State Complexes of Molecules with Calixarenes; 7.6.1: Complexes with Molecular Cations; 7.6.2: Complexes with Neutral Molecules; 7.6.2.1: Complexes in Aqueous Solution; 7.6.2.2: Complexes in Non-aqueous Solution; 7.7: Gas Phase Complexes; 7.8: Theoretical Calculations; 7.9: Templation; 7.9.1: Templation in Calixarene Synthesis; 7.9.2: Calixarenes as Templates; 7.9.3: Templation in Conformational Phenomena; 7.9.4: Allosteric Effects; 7.10: Concluding Remarks; Chapter 8: Using the Baskets: Calixarenes in Action; 8.1: Calixarenes for Separation; 8.1.1: Separation of Ions; 8.1.2: Separation of Molecules; 8.2: Calixarenes as Sensors; 8.2.1: Ion- and Molecule-Selective Electrodes; 8.2.2: Field Effect Transistors; 8.2.3: Chromogenic and Fluorescent Sensors; 8.2.4: Nonlinear Optical Compounds; 8.2.5: Other Sensors; 8.3: Calixarenes as Catalysts; 8.3.1: Biomimetic Catalyst; 8.3.2: Non-Biomimetic Catalysts; 8.4: Calixarenes as Biomimetic and Physiological Compounds; 8.5: Miscellaneous Applications; 8.6: Patent Literature; 8.7:Concluding Remarks

Recenzii

"This updated monograph, with its very logical layout, would be an excellent introduction to this important family of macrocyclic hosts for those interested in entering the field. It will also be very useful as a reference book in institutional libraries and in the personal libraries of practicing supramolecular chemists, including those who work with calixarenes and those who study the behaviors of other related host molecules, such as cyclodextrins or cucurbiturils."

Textul de pe ultima copertă

Calixarenes belong to a family of macrocyclic compounds based on a hydrozyalkylation product of a phenol and an aldehyde, and are probably the world's most readily available synthetic molecular basket. The word calixarene is derived from calyx, Greek for chalice and arene in reference to the presence of aryl groups in the cyclic array. Calixarenes are appealing subjects for research since they can be functionalized in myriad ways to provide interesting and useful materials. As a result of their ease of synthesis they have attracted worldwide attention. Calixarenes An Introduction provides a concise overview of the field with particular attention to the historical development of Calixarenes. Topics covered include how to synthesize and functionalize Calixarenes, examination of Calixarenes properties and applied uses of Calixarenes. The volume contains extensive references to recent literature, offering the reader a valid presentation of information, and will be of immediate value to researchers, as well as graduates and professionals, who require a comprehensive introduction to the subject.

Descriere

This book gives a concise, comprehensive overview of the field with particular attention to the historical development of Calixarenes and will be of immediate value to researchers, graduates and professionals.