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Molecularly Imprinted Polymers for Analytical Chemistry Applications

BOOK

Molecularly Imprinted Polymers for Analytical Chemistry Applications

Wlodzimierz Kutner | Piyush Sindhu Sharma

(2018)

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Additional Information

Book Details

ISBN
978-1-78801-047-4
Edition
1
Language
English
Pages
482
Subjects
Analytical chemistry
Polymer chemistry
Biochemistry
Chemical biology
Materials science

Abstract

There is great interest in the preparation of synthetic receptor-based recognition units for cheap, robust, economic, and selective chemical sensors. Molecular imprinting provides the technology to prepare these synthetic units. There are still more and more syntheses of artificial molecular recognition constructs using analytes or their close structural analogues as templates for molecular imprinting. Stability of complexes of these constructs with the target analytes are often similar to those of biological receptors. Therefore, subsequent polymerization of these complexes results in molecularly imprinted polymers (MIPs) that have a selectivity close to that revealed by natural receptors.

The book summarizes the latest developments and applications of molecular imprinting for selective chemical sensing with each chapter devoted to different analytical applications of molecularly imprinted polymers. Specific chapters include: designing of molecular cavities aided by computational modelling, application of molecularly imprinted polymers for separation as well as sensing of pharmaceuticals and nucleotides.

The book is suitable for academics, postgraduates, and industrial researchers active in analytical chemistry, synthetic organic chemistry, molecular recognition, electrochemistry, and spectroscopy.


Table of Contents

Section Title Page Action Price
Front Cover Cover
Molecularly Imprinted Polymers for Analytical Chemistry Applications i
Preface vii
Contents ix
Chapter 1 - Nano-sized Molecularly Imprinted Polymers as Artificial Antibodies 1
1.1 Molecularly Imprinted Polymers: Different Formats for Different Applications 1
1.2 Advances in the Synthesis of NanoMIPs; Different Approaches to Preparation of MIPs as Nanoparticles 2
1.2.1 Precipitation Polymerisation 5
1.2.2 Mini- and Micro-emulsion Polymerisation 6
1.2.3 Atom Transfer Radical Polymerisation (ATRP) and Reversible Addition-fragmentation Chain Transfer Polymerisation (RAFT) 7
1.2.4 Solid-phase Polymerisation 8
1.3 NanoMIPs as Plastic Antibodies for Bioanalytical Applications 10
1.3.1 NanoMIPs as Sensor Components 11
1.3.1.1 Electrical and Electrochemical Sensors 13
1.3.1.2 Optical Sensors 15
1.3.1.3 Other MIP Chemosensors 17
1.3.2 NanoMIPs in Assays 18
1.3.3 NanoMIPs in Cells and in vivo 19
1.4 Conclusion and Perspectives 22
List of Abbreviations 23
References 24
Chapter 2 - Synthetic Chemistry for Molecular Imprinting 28
2.1 Introduction 28
2.2 Strategic Syntheses of MIPs 29
2.2.1 Interactions Between Templates and Functional Monomers 29
2.2.1.1 Covalent and Semi-covalent Imprinting 31
2.2.1.2 Weak Non-covalent Interactions 32
2.2.1.2.1 Lewis Acid–Base Interactions. 32
2.2.1.2.2 van der Waals Interactions. 32
2.2.1.2.3 Hydrophobic Interactions. 32
2.2.1.3 Electrostatic Interactions 33
2.2.1.4 Metal–Ligand Coordination 33
2.2.2 MIP Synthesis 33
2.2.2.1 Imprinting Strategies 33
2.2.2.1.1 Linear Chain Polymer Cross-linking. 34
2.2.2.1.2 Ligand Chemical Immobilization. 34
2.2.2.1.3. Ligand Physical Entrapment. 35
2.2.1.1.4.Surface Imprinting. 35
2.2.2.2 Polymerization 35
2.2.2.2.1 Polymerization Reactions. 35
2.2.2.2.2 Polymerization Techniques. 37
2.2.2.3 Template Removal 38
2.3 Analytical Applications of MIPs 39
2.3.1 Fabrication of MIP-based Chemosensors 39
2.3.1.1 MIPs with Internal Transducers 40
2.3.1.2 MIPs with External Transducers 40
2.3.2 MIP-based Chemosensors for Analytical Study 40
2.3.2.1 Health Monitoring 42
2.3.2.2 Environment and Food Control 45
2.4 Conclusion 48
List of Abbreviations 48
Acknowledgements 49
References 49
Chapter 3 - Molecularly Imprinted Polymers-based Separation and Sensing of Nucleobases, Nucleosides, Nucleotides and Oligonucleotides 65
3.1 Introduction 65
3.2 Various Approaches to Synthesize MIPs for Nucleic Acids 67
3.2.1 Nucleoside Structures and Conformation 67
3.2.2 Molecularly Imprinted Polymers for Recognition of Purines 68
3.2.3 Molecularly Imprinted Polymer for Recognition of Pyrimidines 74
3.3 MIPs for Extraction and Separation of Nucleic Acid Analogues 76
3.3.1 Molecularly Imprinted Solid-phase Extraction (MISPE) 76
3.3.2 Molecularly Imprinted Solid-phase Microextraction (MISPME) 85
3.3.3 Molecularly Imprinted Matrix Solid-phase Dispersion 86
3.3.4 Molecularly Imprinted Polymers as Stationary Phases 87
3.3.5 Molecularly Imprinted Polymer as Membranes 90
3.4 MIPs as Nucleos(t)ide and Analogue Recognition Units in Chemosensors 95
3.4.1 Electrochemical Sensors with MIPs 96
3.4.2 Piezoelectric Microgravimetry MIP Chemosensors 104
3.4.3 MIP Optical Sensors 108
3.5 Conclusions 115
List of Abbreviations 115
References 118
Chapter 4 - Application of Nanomaterials to Molecularly Imprinted Polymers 124
4.1 Introduction 124
4.2 Introduction to Magnetic Nanoparticles 125
4.3 Methods for the Preparation of Molecularly Imprinted MNPs 127
4.4 Applications of MNPs-MIPs 128
4.4.1 Clinically Directed MNP-MIPs 129
4.4.2 Water Contaminant Recovery and Analysis by MNP-MIPs 132
4.4.3 Food and Feed-related MNP-MIPs 133
4.5 Carbon Nanotubes 134
4.6 Nanotubes Coupled to MIPs: Derivatization Strategies 136
4.7 Nanotubes Coupled to MIPs: Applications 136
4.8 Conclusions 138
List of Abbreviations 139
References 140
Chapter 5 - Molecularly Imprinted Polymer-based Materials for Quantifying Pharmaceuticals 145
5.1 Introduction to Molecularly Imprinted Polymers as Materials for Separation 145
5.2 Validated Analytical Methods for Separation of Pharmaceuticals Using Commercial MIP Sorbents 148
5.3 Inventions and Patents Concerning Molecularly Imprinted Sorbents 158
5.4 Conclusions 162
List of Abbreviations 163
References 163
Chapter 6 - Micro and Nanofabrication of Molecularly Imprinted Polymers 167
6.1 Introduction 167
6.2 Methods of MIP Microfabrication 168
6.2.1 Electropolymerization 169
6.2.2 Optical Methods 169
6.2.3 Mechanical Patterning 176
6.2.4 Soft Lithography 177
6.3 MIP Nanomaterials and Their Fabrication 180
6.3.1 MIP Nanoparticles 181
6.3.1.1 Precipitation Polymerization 181
6.3.1.2 Suspension and Emulsion Polymerizations 182
6.3.1.3 Solid-phase Synthesis of MIPs 183
6.3.2 Nanocomposite MIPs 184
6.3.2.1 Free-radical Polymerization 184
6.3.2.2 Controlled Radical Polymerization 184
6.3.2.3 Core Induced Polymerization 186
6.3.3 Nanotube and Nanowire-based MIPs 186
6.3.3.1 Carbon Nanotubes 186
6.3.3.2 Nanofilaments Obtained Through Porous Alumina Membranes 189
6.4 Conclusions 189
List of Abbreviations 190
References 191
Chapter 7 - Theoretical and Computational Strategies in Molecularly Imprinted Polymer Development 197
7.1 Introduction 197
7.2 Molecular Imprinting from a Thermodynamic Perspective 198
7.3 Computational Strategies for Studying and Developing Molecular Imprinting Systems 201
7.3.1 Introduction 201
7.3.2 Electronic Structure Methods 202
7.3.3 Molecular Dynamics 207
7.3.4 Multivariate Analysis and Other Computational Strategies 213
7.4 Conclusions 217
List of Abbreviations 218
References 218
Chapter 8 - Molecularly Imprinted Polymer-based Optical Chemosensors for Selective Chemical Determinations 227
8.1 Introduction 227
8.2 Fluorescence-based MIP Chemosensors 229
8.2.1 Direct MIP-based Fluorescence Detection 230
8.2.2 Indirect MIP-based Fluorescence Detection Using Labelled Analytes 234
8.2.3 Indirect MIP-based Fluorescence Detection Using Labelled Polymers 237
8.2.3.1 MIP Chemosensors Based on Fluorescent Monomers 237
8.2.3.2 MIP Chemosensors Based on Luminescent Nanoparticles 239
8.3 Chemiluminescence and Electrochemiluminescence-based MIP Chemosensors 246
8.4 Absorption-based MIP Chemosensors 250
8.5 Infrared and Surface-enhanced Raman Scattering (SERS)-based MIP Chemosensors 253
8.6 Surface Plasmon Resonance (SPR)-based MIP Chemosensors 258
8.7 MIP Chemosensors Using Other Optical Transduction Techniques 263
8.8 Conclusions and Outlook 268
List of Abbreviations 269
Acknowledgements 271
References 272
Chapter 9 - Protein Determination Using Molecularly Imprinted Polymer (MIP) Chemosensors 282
9.1 Introduction 282
9.2 Historical Background of Molecular Imprinting 283
9.3 Methods of Protein Imprinting 284
9.3.1 Whole Protein Imprinting 284
9.3.1.1 Piezoelectric Microgravimetry for Protein Sensing 284
9.3.1.2 Electrochemical MIP Chemosensing of Proteins 285
9.3.1.3 Optical Sensing of Proteins 288
9.3.1.4 Imprinting of Immobilized Proteins 291
9.3.1.5 Protein Imprinting in 2-D MIP Films 300
9.3.1.6 MIP Films Deposited on Nanoparticle and Nanoelectrode Surfaces and MIP Nanoparticles 301
9.3.2 Epitope Imprinting 316
9.4 Miscellaneous 318
9.5 Conclusions 320
List of Abbreviations 320
Acknowledgements 323
References 323
Chapter 10 - Water-compatible Molecularly Imprinted Polymers 330
10.1 Introduction 330
10.2 Previous Strategies for the Preparation of MIPs Compatible with Simple Aqueous Samples 332
10.3 Our Approaches to Preparing MIP Micro- or Nanoparticles Compatible with Aqueous Samples and Real Undiluted Biological Sample... 334
10.3.1 Preparation of Water-compatible MIPs via the “Two-step Approach” 335
10.3.2 Preparation of Water-compatible MIPs via “One-step Approach” 346
10.4 Summary and Outlook 351
List of Abbreviations and Symbols 352
Acknowledgements 353
References 353
Chapter 11 - Designing of Biomimetic Molecularly Imprinted Catalysts 359
11.1 Introduction of Biomimetic Catalysts 359
11.2 Development of Biomimetic Molecularly Imprinted Polymers for Catalysis 361
11.2.1 Imprinting with a Transition State Analogue Template 362
11.2.2 Imprinting with Active Sites 366
11.3 Development of Biomimetic Supramolecular Molecularly Imprinted Catalysis 368
11.3.1 Biomimetic Supramolecular Imprinting of Catalysts by Self-assembly 368
11.3.2 Biomimetic Imprinting of Catalysts Using Microgel Matrices 369
11.4 Development of Biomimetic Molecularly Imprinted Polymers for Sensing 372
11.5 Conclusions 374
List of Abbreviations and Symbols 374
Acknowledgements 374
References 375
Chapter 12 - Molecularly Imprinted Polymers: Providing Selectivity to Sample Preparation 379
12.1 Introduction 379
12.2 Molecularly Imprinted Solid-phase Extraction 382
12.2.1 MISPE Modes 382
12.2.1.1 Off-line Protocols 382
12.2.1.2 On-line Protocols 386
12.2.1.3 In-line Protocols 388
12.2.1.4 Improved Batch Protocols 390
12.2.2 Selected Applications 392
12.3 Molecularly Imprinted Solid-phase Microextraction 396
12.3.1 MIP-coated Fibres 397
12.3.2 MIP Fibres (Monoliths) 399
12.4 Molecularly Imprinted Stir Bar Sorptive Extraction 402
12.5 Other Formats 404
12.5.1 Matrix Solid-phase Dispersion 404
12.5.2 Combination of Liquid Membranes and MIPs 404
12.6 Conclusions 405
List of Abbreviations 406
References 407
Chapter 13 - Electrosynthesized Molecularly Imprinted Polymers for Chemosensing: Fundamentals and Applications 412
13.1 Introduction 412
13.2 Pyrrole 417
13.3 o-Phenylenediamine 422
13.4 Thiophene 424
13.5 Phenol 428
13.6 Electrosynthesized MIPs Based on Other Functional Monomers 429
13.7 Composite System Electrosynthesized MIP–Nanomaterials 431
13.8 Conclusions 438
List of Abbreviations and Symbols 440
Acknowledgements 441
References 442
Chapter 14 - Molecularly Imprinted Polymer Sensor Arrays 447
14.1 Introduction 447
14.1.1 Advantages of MIP Sensors 447
14.1.2 Challenges for MIP Sensors 448
14.1.3 MIP Arrays as a Solution 448
14.1.4 Early Examples of MIP Sensor Arrays 450
14.1.5 Outline of the Chapter Goals 452
14.2 Survey of Imprinted Chemosensor Arrays and Assays in the Literature 452
14.3 Design Choices 457
14.3.1 Templates and Analytes 457
14.3.2 Polymer Matrix 458
14.3.3 Polymer Morphologies 459
14.3.4 Sensing Platforms 459
14.3.4.1 Binding Assays 460
14.3.4.2 Summary of Other Signaling Mechanisms 460
14.3.5 Data Processing for Chemosensor Arrays 460
14.3.5.1 Introduction to Chemosensor Array Signal Processing 460
14.3.5.2 Principal Component Analysis (PCA) 461
14.3.5.3 Linear Discriminant Analysis (LDA) 462
14.3.5.4 Other Methods 463
14.4 Literature Studies 463
14.4.1 Example 1: Imprinted Photonic Polymer Array for Detection of Polybrominated Flame Retardants 464
14.4.2 Example 2: Protein Imprinted Hydrogel Array for Electrochemical Protein Profiling 464
14.4.3 Example 3: MIP Array for Discrimination of Water-soluble Azo Dyes 467
14.4.4 Example 4: An Imprinted Titania Array for Discrimination of Small Organic Acids 467
14.4.5 Example 5: MIP-coated QCM Chemosensor Array for Detection of Low-molecular-weight Aldehydes 469
14.5 Conclusion 470
List of Abbreviations and Symbols 471
Acknowledgement 472
References 472
Subject Index 475

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