Calixarenes: an introduction
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Cambridge
RSC Publ.
2008
|
| Edition: | 2. ed. |
| Series: | Monographs in supramolecular chemistry
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XIII, 276 S. Ill., graph. Darst. |
| ISBN: | 9780854042586 |
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MARC
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| 100 | 1 | |a Gutsche, Carl D. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Calixarenes |b an introduction |c C. David Gutsche |
| 250 | |a 2. ed. | ||
| 264 | 1 | |a Cambridge |b RSC Publ. |c 2008 | |
| 300 | |a XIII, 276 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 0 | |a Monographs in supramolecular chemistry | |
| 650 | 4 | |a Calixarenes | |
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Record in the Search Index
| _version_ | 1804137403562065920 |
|---|---|
| adam_text | Contents
Chapter 1 From Resinous Tar to Molecular Baskets
1.1 The Resinous Tar 1
1.2 Glistening Crystals: The Zinke Products 5
1.3 More Crystals: The Niederl Products 9
1.4 Cyclic Tetramers: Proofs of Structure 11
1.5 The Petrolite Chapter 15
1.6 Cyclic Tetramers and the Quest for Enzyme Mimics 18
1.7 Unraveling the Literature 21
1.8 Nomenclature and Representation of the Calixarenes 24
Chapter 2 Making the Baskets: Synthesis of Calixarenes
2.1 One-step, Base-induced Synthesis
of Phenol-derived Calixarenes 27
2.1.1 Synthesis of p-rerr-Butylcalixarenes 27
2.1.2 Synthesis of Other/^-Substituted Calixarenes 31
2.2 One-step, Acid-catalyzed Synthesis of Calixarenes 34
2.2.1 Phenol-derived Calixarenes 34
2.2.2 Resorcinol-derived Calixarenes 34
2.3 Multi-step Synthesis of Calixarenes 37
2.3.1 Non-convergent Stepwise Syntheses 37
2.3.2 Convergent Stepwise Syntheses (Fragment
Condensation Procedure) 39
2.4 Synthesis of Calixarene-related Compounds 45
2.4.1 Norcalixarenes and Homocalixarenes 45
2.4.2 Oxacalixarenes, Azacalixarenes
and Thiacalixarenes 47
2.4.3 Homooxacalixarenes and Homoazacalixarenes 49
2.4.4 Heterocalixarenes 51
2.5 Mechanism of Calixarene-forming Reactions 53
2.5.1 Mechanism of the Base-induced Reaction 53
2.5.2 Mechanism of the Acid-catalyzed Reaction 59
2.6 Concluding Remarks 60
viii
Contents ix
Chapter 3 Proving the Baskets: The Characterization and Properties
of Calixarenes
3.1 Separation and Purification of Calixarenes 62
3.2 X-Ray Crystallography: The Ultimate Proof
of Structure 63
3.3 Physical Properties of Calixarenes 64
3.3.1 Melting Points 64
3.3.2 Solubilities 66
3.3.3 pKa Values 66
3.4 Dipole Moments of Calixarenes 70
3.5 Spectral Properties of Calixarenes 70
3.5.1 Infrared Spectra 70
3.5.2 Ultraviolet Spectra 71
3.5.3 NMR Spectra 72
3.5.4 Mass Spectra 74
3.6 Concluding Remarks 76
Chapter 4 Shaping the Baskets: Conformations of Calixarenes
4.1 Conformational Representation and Nomenclature 77
4.2 Computational Studies of Calixarene Conformations 81
4.3 Conformations of Calixarenes in the Solid State 83
4.3.1 Calix[4]arenes 83
4.3.2 Calix[5]arenes 86
4.3.3 Calix[6]arenes 86
4.3.4 Calix[7]arenes 87
4.3.5 Calix[8]arenes 87
4.3.6 Large Calixarenes 88
4.4 Conformations of Flexible Calixarenes in Solution 88
4.4.1 Conformational Mobility of Calix[«]arenes 88
4.4.1.1 Conformations of Calix[4]arenes 89
4.4.1.2 Conformational Mobility of
Calixarenes Larger than
Calix[4]arenes 93
4.4.1.3 Conformational Mobility of
Oxacalixarenes and Azacalixarenes 93
4.4.1.4 Conformational Mobility of
Calixresorcarenes and C-Substituted
Calixarenes 94
4.4.1.5 Conformational Mobility of
Thiacalixarenes 96
4.4.1.6 Conformational Mobility of
Calixarene Ethers, Deoxycalixarenes,
Calixquinones and Calixarenethiols 97
x Contents
4.4.2 Pathways for Cone-cone Interconversion
of Calix[4]arenes 98
4.5 Conformationally Immobile Calixarenes 99
4.5.1 Minimum Structural Requirements
for Conformational Immobility of Unbridged
Calixarene Ethers and Esters 99
4.5.1.1 Identification of Fixed Conformers 99
4.5.1.2 Fully Etherified and Esterified
Calixarenes 99
4.5.1.3 Partially Etherified and Esterified
Calixarenes 103
4.5.1.4 Meta-substituted Calixarenes 104
4.5.2 Conformational Immobilization
via Bridging 104
4.5.3 Conformational Freezing via Oxygen-Metal
Bridges 107
4.6 Factors Governing the Conformational Outcome
of Derivatization 109
4.6.1 O-Tetrasubstitution of Calix[4]arenes 109
4.6.2 Mono-, Di- and Tri-O-substitution
of Calix[4]arenes 111
4.6.3 O-Substitution of Calix[5]arenes
and Calix[6]arenes 111
4.6.4 Calixarene Oxyanions 112
4.6.4.1 Calix[4]arene Oxyanions 112
4.6.4.2 Calix[6]arene Oxyanions 112
4.7 Chiral Calixarenes 113
4.8 Concluding Remarks 115
Chapter 5 Embroidering the Baskets: Introduction of Functional
Groups
5.1 Functionalization Involving the OH Groups 116
5.1.1 Esterification 116
5.1.2 Etherification 118
5.1.2.1 With Simple Alkyl Halides 118
5.1.2.2 With Functionalized Alkylating
Agents 122
5.1.3 Endo Rim-bridged Calixarenes 123
5.1.4 Replacement of OH with H, N and S 127
5.2 Modifying the Exo Rim of Calixarenes 129
5.2.1 General Overview 129
5.2.2 Halogenation, Nitration, Sulfonation
and Diazonium Coupling Routes 130
5.2.3 Alkylation (Including Chloromethylation)
Route 133
Contents xi
5.2.4 Acylation and Aroylation Routes 134
5.2.5 Arylation Reactions 135
5.2.6 Aminomethylation: The p-Quinonemethide
Route 135
5.2.7 /?-Claisen Rearrangement Route 136
5.3 Functionalization of the Methylene Bridges 138
5.4 Exo Rim-Bridged Calixarenes 140
5.5 Oxidation of Calixarenes 141
5.5.1 Calixquinones 141
5.5.2 Spirodienones 143
5.6 Reduction of Calixarenes 144
5.7 Selective Functionalization 145
5.8 Concluding Remarks 146
Chapter 6 Combining the Baskets: Multi-Calixarenes
6.1 Calixarenes Intermolecularly Bridged
by Covalent Bonding 148
6.1.1 Bridging via the Endo Rims 148
6.1.2 Bridging via the Exo Rims 150
6.1.3 Multi-Calixarenes and Calixarene Dendrimers 152
6.2 Calixarenes Intermolecularly Bridged
by Non-covalent Bonding 154
6.2.1 Dimeric Assemblies of Calixarenes 154
6.2.2 Catenanes and Rotaxanes 157
6.2.3 Oligomeric and Polymeric Assemblies
of Calixarenes 158
6.2.4 Calixarenes in Monolayers
and Interfaces 160
6.3 Calixarene Polymers 162
6.4 Concluding Remarks 163
Chapter 7 Filling the Baskets: Complex Formation with Calixarenes
7.1 Solid State Complexes 164
7.2 Solution State Complexes of Metal Cations
with Endo Rim-substituted Calixarenes 171
7.2.1 Complexation with Parent Calixarenes 172
7.2.2 Complexation with Endo Rim-substituted
Calixarenes 173
7.2.2.1 Endo Rim Ethers 173
7.2.2.2 Endo Rim Esters 175
7.2.2.3 Endo Rim Ketones 176
7.2.2.4 Endo Rim Amides 177
xii Contents
7.2.2.5 Endo Rim Carboxylic Acids 178
7.2.2.6 Endo Rim Phosphorus- and Sulfur-
containing Groups 180
7.2.2.7 Nitrogen-containing Chelating
Groups on the Endo Rim 181
7.2.3 Calixcrowns 182
7.2.4 Calixspherands 186
7.3 Solution State Complexes of Metal Cations
with Exo Rim-substituted Calixarenes 187
7.4 Anion Complexes with Calixarenes 188
7.5 Salt Complexes with Calixarenes 191
7.6 Solution State Complexes of Molecules
with Calixarenes 193
7.6.1 Complexes with Molecular Cations 193
7.6.2 Complexes with Neutral Molecules 197
7.6.2.1 Complexes in Aqueous Solution 197
7.6.2.2 Complexes in Non-aqueous
Solution 199
7.7 Gas Phase Complexes 203
7.8 Theoretical Calculations 204
7.9 Templation 204
7.9.1 Templation in Calixarene Synthesis 204
7.9.2 Calixarenes as Templates 204
7.9.3 Templation in Conformational
Phenomena 205
7.9.4 Allosteric Effects 206
7.10 Concluding Remarks 207
Chapter 8 Using the Baskets: Calixarenes in Action
8.1 Calixarenes for Separations 209
8.1.1 Separations of Ions 209
8.1.2 Separations of Molecules 210
8.2 Calixarenes as Sensors 211
8.2.1 Ion- and Molecule-selective Electrodes 212
8.2.2 Field Effect Transistors 214
8.2.3 Chromogenic and Fluorescent Sensors 216
8.2.4 Nonlinear Optical Compounds 218
8.2.5 Other Sensors 220
8.3 Calixarenes as Catalysts 220
8.3.1 Biomimetic Catalysts 220
8.3.2 Non-biomimetic Catalysts 225
8.4 Calixarenes as Biomimetic and Physiological
Compounds 228
Contents xiii
8.5 Miscellaneous Applications 231
8.6 Patent Literature 236
8.7 Concluding Remarks 237
Appendices 238
Author Index 244
Subject Index 261
|
| adam_txt |
Contents
Chapter 1 From Resinous Tar to Molecular Baskets
1.1 The Resinous Tar 1
1.2 Glistening Crystals: The Zinke Products 5
1.3 More Crystals: The Niederl Products 9
1.4 Cyclic Tetramers: Proofs of Structure 11
1.5 The Petrolite Chapter 15
1.6 Cyclic Tetramers and the Quest for Enzyme Mimics 18
1.7 Unraveling the Literature 21
1.8 Nomenclature and Representation of the Calixarenes 24
Chapter 2 Making the Baskets: Synthesis of Calixarenes
2.1 One-step, Base-induced Synthesis
of Phenol-derived Calixarenes 27
2.1.1 Synthesis of p-rerr-Butylcalixarenes 27
2.1.2 Synthesis of Other/^-Substituted Calixarenes 31
2.2 One-step, Acid-catalyzed Synthesis of Calixarenes 34
2.2.1 Phenol-derived Calixarenes 34
2.2.2 Resorcinol-derived Calixarenes 34
2.3 Multi-step Synthesis of Calixarenes 37
2.3.1 Non-convergent Stepwise Syntheses 37
2.3.2 Convergent Stepwise Syntheses (Fragment
Condensation Procedure) 39
2.4 Synthesis of Calixarene-related Compounds 45
2.4.1 Norcalixarenes and Homocalixarenes 45
2.4.2 Oxacalixarenes, Azacalixarenes
and Thiacalixarenes 47
2.4.3 Homooxacalixarenes and Homoazacalixarenes 49
2.4.4 Heterocalixarenes 51
2.5 Mechanism of Calixarene-forming Reactions 53
2.5.1 Mechanism of the Base-induced Reaction 53
2.5.2 Mechanism of the Acid-catalyzed Reaction 59
2.6 Concluding Remarks 60
viii
Contents ix
Chapter 3 Proving the Baskets: The Characterization and Properties
of Calixarenes
3.1 Separation and Purification of Calixarenes 62
3.2 X-Ray Crystallography: The Ultimate Proof
of Structure 63
3.3 Physical Properties of Calixarenes 64
3.3.1 Melting Points 64
3.3.2 Solubilities 66
3.3.3 pKa Values 66
3.4 Dipole Moments of Calixarenes 70
3.5 Spectral Properties of Calixarenes 70
3.5.1 Infrared Spectra 70
3.5.2 Ultraviolet Spectra 71
3.5.3 NMR Spectra 72
3.5.4 Mass Spectra 74
3.6 Concluding Remarks 76
Chapter 4 Shaping the Baskets: Conformations of Calixarenes
4.1 Conformational Representation and Nomenclature 77
4.2 Computational Studies of Calixarene Conformations 81
4.3 Conformations of Calixarenes in the Solid State 83
4.3.1 Calix[4]arenes 83
4.3.2 Calix[5]arenes 86
4.3.3 Calix[6]arenes 86
4.3.4 Calix[7]arenes 87
4.3.5 Calix[8]arenes 87
4.3.6 Large Calixarenes 88
4.4 Conformations of Flexible Calixarenes in Solution 88
4.4.1 Conformational Mobility of Calix[«]arenes 88
4.4.1.1 Conformations of Calix[4]arenes 89
4.4.1.2 Conformational Mobility of
Calixarenes Larger than
Calix[4]arenes 93
4.4.1.3 Conformational Mobility of
Oxacalixarenes and Azacalixarenes 93
4.4.1.4 Conformational Mobility of
Calixresorcarenes and C-Substituted
Calixarenes 94
4.4.1.5 Conformational Mobility of
Thiacalixarenes 96
4.4.1.6 Conformational Mobility of
Calixarene Ethers, Deoxycalixarenes,
Calixquinones and Calixarenethiols 97
x Contents
4.4.2 Pathways for Cone-cone Interconversion
of Calix[4]arenes 98
4.5 Conformationally Immobile Calixarenes 99
4.5.1 Minimum Structural Requirements
for Conformational Immobility of Unbridged
Calixarene Ethers and Esters 99
4.5.1.1 Identification of Fixed Conformers 99
4.5.1.2 Fully Etherified and Esterified
Calixarenes 99
4.5.1.3 Partially Etherified and Esterified
Calixarenes 103
4.5.1.4 Meta-substituted Calixarenes 104
4.5.2 Conformational Immobilization
via Bridging 104
4.5.3 Conformational Freezing via Oxygen-Metal
Bridges 107
4.6 Factors Governing the Conformational Outcome
of Derivatization 109
4.6.1 O-Tetrasubstitution of Calix[4]arenes 109
4.6.2 Mono-, Di- and Tri-O-substitution
of Calix[4]arenes 111
4.6.3 O-Substitution of Calix[5]arenes
and Calix[6]arenes 111
4.6.4 Calixarene Oxyanions 112
4.6.4.1 Calix[4]arene Oxyanions 112
4.6.4.2 Calix[6]arene Oxyanions 112
4.7 Chiral Calixarenes 113
4.8 Concluding Remarks 115
Chapter 5 Embroidering the Baskets: Introduction of Functional
Groups
5.1 Functionalization Involving the OH Groups 116
5.1.1 Esterification 116
5.1.2 Etherification 118
5.1.2.1 With Simple Alkyl Halides 118
5.1.2.2 With Functionalized Alkylating
Agents 122
5.1.3 Endo Rim-bridged Calixarenes 123
5.1.4 Replacement of OH with H, N and S 127
5.2 Modifying the Exo Rim of Calixarenes 129
5.2.1 General Overview 129
5.2.2 Halogenation, Nitration, Sulfonation
and Diazonium Coupling Routes 130
5.2.3 Alkylation (Including Chloromethylation)
Route 133
Contents xi
5.2.4 Acylation and Aroylation Routes 134
5.2.5 Arylation Reactions 135
5.2.6 Aminomethylation: The p-Quinonemethide
Route 135
5.2.7 /?-Claisen Rearrangement Route 136
5.3 Functionalization of the Methylene Bridges 138
5.4 Exo Rim-Bridged Calixarenes 140
5.5 Oxidation of Calixarenes 141
5.5.1 Calixquinones 141
5.5.2 Spirodienones 143
5.6 Reduction of Calixarenes 144
5.7 Selective Functionalization 145
5.8 Concluding Remarks 146
Chapter 6 Combining the Baskets: Multi-Calixarenes
6.1 Calixarenes Intermolecularly Bridged
by Covalent Bonding 148
6.1.1 Bridging via the Endo Rims 148
6.1.2 Bridging via the Exo Rims 150
6.1.3 Multi-Calixarenes and Calixarene Dendrimers 152
6.2 Calixarenes Intermolecularly Bridged
by Non-covalent Bonding 154
6.2.1 Dimeric Assemblies of Calixarenes 154
6.2.2 Catenanes and Rotaxanes 157
6.2.3 Oligomeric and Polymeric Assemblies
of Calixarenes 158
6.2.4 Calixarenes in Monolayers
and Interfaces 160
6.3 Calixarene Polymers 162
6.4 Concluding Remarks 163
Chapter 7 Filling the Baskets: Complex Formation with Calixarenes
7.1 Solid State Complexes 164
7.2 Solution State Complexes of Metal Cations
with Endo Rim-substituted Calixarenes 171
7.2.1 Complexation with Parent Calixarenes 172
7.2.2 Complexation with Endo Rim-substituted
Calixarenes 173
7.2.2.1 Endo Rim Ethers 173
7.2.2.2 Endo Rim Esters 175
7.2.2.3 Endo Rim Ketones 176
7.2.2.4 Endo Rim Amides 177
xii Contents
7.2.2.5 Endo Rim Carboxylic Acids 178
7.2.2.6 Endo Rim Phosphorus- and Sulfur-
containing Groups 180
7.2.2.7 Nitrogen-containing Chelating
Groups on the Endo Rim 181
7.2.3 Calixcrowns 182
7.2.4 Calixspherands 186
7.3 Solution State Complexes of Metal Cations
with Exo Rim-substituted Calixarenes 187
7.4 Anion Complexes with Calixarenes 188
7.5 Salt Complexes with Calixarenes 191
7.6 Solution State Complexes of Molecules
with Calixarenes 193
7.6.1 Complexes with Molecular Cations 193
7.6.2 Complexes with Neutral Molecules 197
7.6.2.1 Complexes in Aqueous Solution 197
7.6.2.2 Complexes in Non-aqueous
Solution 199
7.7 Gas Phase Complexes 203
7.8 Theoretical Calculations 204
7.9 Templation 204
7.9.1 Templation in Calixarene Synthesis 204
7.9.2 Calixarenes as Templates 204
7.9.3 Templation in Conformational
Phenomena 205
7.9.4 Allosteric Effects 206
7.10 Concluding Remarks 207
Chapter 8 Using the Baskets: Calixarenes in Action
8.1 Calixarenes for Separations 209
8.1.1 Separations of Ions 209
8.1.2 Separations of Molecules 210
8.2 Calixarenes as Sensors 211
8.2.1 Ion- and Molecule-selective Electrodes 212
8.2.2 Field Effect Transistors 214
8.2.3 Chromogenic and Fluorescent Sensors 216
8.2.4 Nonlinear Optical Compounds 218
8.2.5 Other Sensors 220
8.3 Calixarenes as Catalysts 220
8.3.1 Biomimetic Catalysts 220
8.3.2 Non-biomimetic Catalysts 225
8.4 Calixarenes as Biomimetic and Physiological
Compounds 228
Contents xiii
8.5 Miscellaneous Applications 231
8.6 Patent Literature 236
8.7 Concluding Remarks 237
Appendices 238
Author Index 244
Subject Index 261 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author | Gutsche, Carl D. |
| author_facet | Gutsche, Carl D. |
| author_role | aut |
| author_sort | Gutsche, Carl D. |
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| ctrlnum | (OCoLC)192026874 (DE-599)BVBBV023162271 |
| dewey-full | 547.632 |
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| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.632 |
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| discipline | Chemie / Pharmazie Chemie |
| discipline_str_mv | Chemie / Pharmazie Chemie |
| edition | 2. ed. |
| format | Book |
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| id | DE-604.BV023162271 |
| illustrated | Illustrated |
| index_date | 2024-07-02T19:55:01Z |
| indexdate | 2024-07-09T21:11:45Z |
| institution | BVB |
| isbn | 9780854042586 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016332568 |
| oclc_num | 192026874 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-29T DE-11 |
| owner_facet | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-29T DE-11 |
| physical | XIII, 276 S. Ill., graph. Darst. |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | RSC Publ. |
| record_format | marc |
| series2 | Monographs in supramolecular chemistry |
| spelling | Gutsche, Carl D. Verfasser aut Calixarenes an introduction C. David Gutsche 2. ed. Cambridge RSC Publ. 2008 XIII, 276 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Monographs in supramolecular chemistry Calixarenes Metacyclophane (DE-588)4227079-0 gnd rswk-swf Metacyclophane (DE-588)4227079-0 s DE-604 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016332568&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Gutsche, Carl D. Calixarenes an introduction Calixarenes Metacyclophane (DE-588)4227079-0 gnd |
| subject_GND | (DE-588)4227079-0 |
| title | Calixarenes an introduction |
| title_auth | Calixarenes an introduction |
| title_exact_search | Calixarenes an introduction |
| title_exact_search_txtP | Calixarenes an introduction |
| title_full | Calixarenes an introduction C. David Gutsche |
| title_fullStr | Calixarenes an introduction C. David Gutsche |
| title_full_unstemmed | Calixarenes an introduction C. David Gutsche |
| title_short | Calixarenes |
| title_sort | calixarenes an introduction |
| title_sub | an introduction |
| topic | Calixarenes Metacyclophane (DE-588)4227079-0 gnd |
| topic_facet | Calixarenes Metacyclophane |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016332568&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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