Advanced molecularly imprinting materials

709 Pages·2017·29.803 MB·English

by  Tiwari, Ashutosh, Uzun, Lokman

Advanced Molecularly
Imprinting Materials
Scrivener Publishing
100 Cummings Center, Suite 541J
Beverly, MA 01915-6106
Advanced Materials Series
The Advanced Materials Series provides recent advancements of the fascinating
field of advanced materials science and technology, particularly in the area of
structure, synthesis and processing, characterization, advanced-state properties,
and applications. The volumes will cover theoretical and experimental
approaches of molecular device materials, biomimetic materials, h ybrid-type
composite materials, functionalized polymers, supramolecular systems,
information- and energy-transfer materials, biobased and biodegradable or
environmental friendly materials. Each volume will be devoted to one broad
subject and the multidisciplinary aspects will be drawn out in full.
Series Editor: Ashutosh Tiwari
Biosensors and Bioelectronics Centre
Linköping University
SE-581 83 Linköping
Sweden
E-mail: [email protected]
Managing Editors: Sachin Mishra and Sophie Thompson
Publishers at Scrivener
Martin Scrivener ([email protected])
Phillip Carmical ([email protected])
Advanced Molecularly
Imprinting Materials
Edited by
Ashutosh Tiwari and Lokman Uzun
Copyright © 2017 by Scrivener Publishing LLC. All rights reserved.
Co-published by John Wiley & Sons, Inc. Hoboken, New Jersey, and Scrivener Publishing LLC, Beverly,
Massachusetts.
Published simultaneously in Canada.
No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or
by any means, electronic, mechanical, photocopying, recording, scanning, or other wise, except as permit-
ted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior writ-
ten permission of the Publisher, or authorization through payment of the appropriate per-copy fee to
the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, [phone], fax
[phone], or on the web at www.copyright.com. Requests to the Publisher for permission should be
addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030,
[phone], fax [phone], or online at http://www.wiley.com/go/permission.
Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts
in preparing this book, they make no representations or warranties with respect to the accuracy or
completeness of the contents of this book and specifically disclaim any implied warranties of merchant-
ability or fitness for a particular purpose. No warranty may be created or extended by sales representa-
tives or written sales materials. The advice and strategies contained herein may not be suitable for your
situation. You should consult with a professional where appropriate. Neither the publisher nor author
shall be liable for any loss of profit or any other commercial damages, including but not limited to spe-
cial, incidental, consequential, or other damages.
For general information on our other products and services or for technical support, please contact
our Customer Care Department within the United States at [phone], outside the United States at
[phone] or fax [phone].
Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may
not be available in electronic formats. For more information about Wiley products, visit our web site
at www.wiley.com.
For more information about Scrivener products please visit www.scrivenerpublishing.com.
Cover design by Russell Richardson
Library of Congr ess Cataloging-in-Publication Data:
Names: Tiwari, Ashutosh, 1978- editor. | Uzun, Lokman, editor.
Title: Advanced molecularly imprinting materials / edited by Ashutosh Tiwari
and Lokman Uzun.
Other titles: Advanced materials series (Scrivener Publishing).
Description: Hoboken, New Jersey : John Wiley & Sons, Inc. ; Beverly,
Massachusetts : Scrivener Publishing LLC, [2017] | Series: Advanced
material series | Includes index.
Identifiers: LCCN 2016039439 (print) | LCCN 2016039851 (ebook) |
ISBN 9781119336297 (hardback) | ISBN 9781119336310 (pdf) | ISBN 9781119336167 (epub)
Subjects: | MESH: Molecular Imprinting | Polymers--chemistry | Polymerization | Biotechnology
Classification: LCC TP156.P6 (print) | LCC TP156.P6 (ebook) | NLM QT 37.5.P7 | DDC 668.9/2--dc23
LC record available at https://lccn.loc.gov/2016039439
ISBN 978-1-119-33629-7
Printed in the United States of America
10 9 8 7 6 5 4 3 2 1
Contents
Preface xvii
Part 1 Strategies of Affinity Materials
1 Recent Molecularly Imprinted Polymer-based
Methods for Sample Preparation 3
Antonio Martín-Esteban
1.1 Introduction 3
1.2 Molecularly Imprinted Solid-phase Extraction 6
1.2.1 General Considerations 6
1.2.2 Online and Inline Protocols 11
1.2.3 Improved Batch Protocols 13
1.3 Molecularly Imprinted Solid-phase Microextraction 14
1.3.1 MIP-coated Fibers 14
1.3.2 MIP Fibers (Monoliths) 16
1.4 Molecularly Imprinted Stir Bar Sorptive Extraction 17
1.5 Other Formats 18
1.5.1 Matrix Solid-phase Dispersion 18
1.5.2 Liquid Membranes and MIPs Combination 19
1.6 Conclusions 21
References 21
2 A Genuine Combination of Solvent-free Sample Preparation
Technique and Molecularly Imprinted Nanomaterials 29
Santanu Patra, Ekta Roy, Rashmi Madhuri and
Prashant K. Sharma
2.1 Introduction 30
2.1.1 The Overview 30
2.1.2 General Procedure for Solid-phase
Microextraction and Their Basic Components 33
v
vi Contents
2.1.3 Some Recent Examples of Solid-phase
Microextraction Technique and Their Reviews 36
2.1.4 Selectivity Problem: Introduction of Molecularly
Imprinted Polymer (MIP) 37
2.2 Molecularly Imprinted Polymer Modified Fiber
for Solid-phase Microextraction 40
2.2.1 MISPME Using Modified Silica fiber as
Stationary Phase 40
2.2.2 MISPME Using Modified Metal Fiber as
Stationary Phase 49
2.2.3 Other MISPME Fibers 54
2.3 In-tube Solid-phase Microextraction Technique 55
2.4 Monolithic Fiber 58
2.5 Micro-solid-phase Extraction 70
2.6 Stir-bar Sorptive Extraction 73
2.7 Conclusion and Future Scope 76
Acknowledgments 76
Abbreviations 77
References 78
3 Fluorescent Molecularly Imprinted Polymers 89
Kornelia Gawlitza, Wei Wan, Sabine Wagner
and Knut Rurack
3.1 Introduction 89
3.2 Classes of Emitters to Endow MIPs with Fluorescence 91
3.2.1 Fluorescent Dyes 91
3.2.1.1 Changes in the Local Environment
Induced by Template Rebinding 92
3.2.1.2 Hydrogen-bonding Interactions Between
Template and Fluorescent Dye 95
3.2.1.3 Electrostatic Interactions Between
Template and Fluorescent Dye 96
3.2.1.4 Coordinative Interactions Between
Template and Fluorescent Dye 97
3.2.1.5 Covalent Bonds Between Template
and Fluorescent Dye 98
3.2.2 Fluorescent Probes 99
3.2.3 Lanthanide-based Systems 101
3.2.4 Quantum Dots 103
3.2.5 Carbon Dots 105
3.2.6 Upconversion Nanoparticles 107
Contents vii
3.3 Fluorescent Molecularly Imprinted Silica 108
3.4 Post-imprinting of MIPs 111
3.5 fMIPs as Labels 113
3.6 Formats for fMIPs 115
3.6.1 Bulk fMIPs 115
3.6.2 fMIP Films 116
3.6.3 fMIPs-containing Micro- and Nanoparticles 117
3.7 Conclusion 119
References 120
4 Molecularly Imprinted Polymer-based Micro- and
Nanotraps for Solid-phase Extraction 129
Rıdvan Say, Rüstem Keçili and Arzu Ersöz
4.1 Introduction 130
4.2 MIPs as SPE Materials 130
4.2.1 MIP-based SPE for Environmental Samples 132
4.2.2 MIP-based SPE for Biological Samples 142
4.2.3 MIP-based SPE for Food and Beverage Samples 148
4.3 Conclusions 149
References 153
5 Imprinted Carbonaceous Nanomaterials: A Tiny Looking
Big Thing in the Field of Selective and Specific Analysis 165
Ekta Roy, Santanu Patra, Rashmi Madhuri and
Prashant K. Sharma
5.1 Introduction 166
5.1.1 Popularly Used Carbon-based Nanomaterials 169
5.1.1.1 Graphene 169
5.1.1.2 Carbon Nanotubes 172
5.1.1.3 Graphene Quantum Dots/Carbon
Nanodots 174
5.1.1.4 Problems in Their Use 175
5.1.2 Introduction of Molecularly Imprinted Polymers
as a Selectivity Factor 176
5.1.3 Combination of MIPs and Carbonaceous
Nanomaterials: Solution for Each Other 178
5.2 Graphene-modified Imprinted Polymer 179
5.2.1 Graphene-modified Imprinted Polymer in
Combination with Nanoparticle 182
5.3 Carbon Nanotubes-modified Imprinted Polymer 190
viii Contents
5.4 Combination of Graphene, CNTs, and MIPs 196
5.5 Graphene Quantum Dots and/or Carbon Dots 198
5.6 Fullerene 201
5.7 Activated Carbon 202
5.8 Conclusions 203
Acknowledgments 204
List of Abbreviations 204
References 205
6 Molecularly Imprinted Materials for Fiber-optic
Sensor Platforms 217
Yavuz Orhan Yaman, Necdet Başaran, Kübra Karayagiz,
Zafer Vatansever, Cengiz Yegin, Önder Haluk Tekbaş
and Müfrettin Murat Sari
6.1 Introduction 218
6.1.1 General Information 218
6.1.2 General Principle of Molecular
Imprinting Materials 219
6.1.2.1 Characterization of Molecularly
Imprinted Polymers 221
6.1.3 General Detection Principle and Molecular
Aspect of MIPs for FO Sensors 222
6.2 Material Aspect: Morphology and Physical Forms
of MIPs in FO Sensors 223
6.2.1 Morphology 223
6.2.2 Physical Forms 225
6.2.2.1 Microsphere 226
6.2.2.2 Nanoparticles 227
6.2.2.3 MIPs Layers/Thin Films 229
6.3 Molecularly Imprinting Technology for
Fiber-optic Sensors 231
6.3.1 General Principle of Fiber-optic Sensing 231
6.3.1.1 Extrinsic Sensing 232
6.3.1.2 Intrinsic Sensing 233
6.3.1.3 Application Areas 234
6.3.2 Sensing Functionalities and Mechanisms
of Current FO Sensors 235
6.3.2.1 Fluorescence-based FOs 236
6.3.2.2 Absorption-based FOs 240
6.3.2.3 Reflectance-based FOs 241
Contents ix
6.3.2.4 Resonance-based Sensors 246
6.3.2.5 Classification Based on
Modulation Types 248
6.3.3 Design of MIPs for Fiber-optic Sensors 248
6.3.3.1 Design Process of MIPs 248
6.3.3.2 Development and Optimization of MIPs 252
6.3.3.3 Synthesis of MIPs 255
6.3.4 Characterization Methods for MIPs 260
6.3.4.1 Chemical Characterization 261
6.3.4.2 Morphological Characterization 262
6.3.4.3 Binding Behavior Characterization 264
6.4 State-of-the-art Fiber-optic Sensors Applications Using
Molecularly Imprinted Materials 268
6.5 Conclusion 273
References 274
Part 2 Rational Design of MIP for Advanced Applications
7 Molecularly Imprinted Polymer-based Sensors
for Biomedical and Environmental Applications 285
Anca Florea, Oana Hosu, Bianca Ciui and Cecilia Cristea
7.1 Introduction 285
7.1.1 General Aspects of Molecularly
Imprinting Technology 286
7.1.2 Synthesis Strategies for MIPs 289
7.1.3 MIP Polymerization Strategies 289
7.1.4 Molecular Imprinted Polymer Bonding
Techniques 292
7.1.4.1 Covalent Bond Method
(Pre-assembly Method) 292
7.1.4.2 Noncovalent Method
(Self-assembly Method) 292
7.1.4.3 Semicovalent Imprinting 292
7.1.4.4 Imprinting via Metal Coordination 293
7.1.4.5 Combinatorial Imprinting 293
7.1.5 Detection Methods for Molecularly Imprinted
Polymer-based Sensors 293
7.1.5.1 Optical Detection Methods 293
7.1.5.2 Piezoelectrical Detection Methods 295
7.1.5.3 Electrochemical Detection Methods 295
x Contents
7.2 Molecularly Imprinted Polymers for Analytes
of Biomedical Interest 296
7.2.1 Motivation and Interest of Developing
Molecularly Imprinted Polymers in the
Biomedical Filed 296
7.2.2 The Pretreatment of Biological Samples
When Using Molecularly Imprinted
Polymer-based Sensors 297
7.2.3 Electrochemical Sensors Based on Molecularly
Imprinted Polymers 298
7.2.4 Massic Sensors Based on Molecularly
Imprinted Polymers 304
7.2.5 Optical Sensors Based on Molecularly
Imprinted Polymers 304
7.3 Molecularly Imprinted Polymers for Analytes
of Environmental Interest 306
7.3.1 Pesticides 307
7.3.2 Explosives and Warfare Agents 312
7.4 Conclusion 314
Acknowledgments 316
References 316
8 Molecularly Imprinted Polymers: The Affinity Adsorbents
for Environmental Biotechnology 327
Bo Mattiasson and Gizem Ertürk
8.1 Introduction 327
8.2 Molecularly Imprinted Polymers 329
8.2.1 Monomers 329
8.2.2 Cross-linking Agents 331
8.2.3 Mode of Polymerization 332
8.3 Cryogels 334
8.4 Process Technology 336
8.5 Applications 338
8.5.1 Example: Capture of Compounds Binding
to Estrogen Receptors 338
8.5.2 Example: Capture of Pesticides 338
8.5.3 Example: Capture of Pharmaceuticals and
Their Metabolites 339
8.5.4 Example: Capture of Heavy-metal Ions 339