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Design and Development of Molecularly Imprinted Polymers and Imprinted Sensors

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Design and Development of Molecularly Imprinted Polymers and Imprinted Sensors ADVERTIMENT. Lʼaccés als continguts dʼaquesta tesi queda condicionat a lʼacceptació de les condicions dʼús establertes per la següent llicència Creative Commons: http://cat.creativecommons.org/?page_id=184 ADVERTENCIA. El acceso a los contenidos de esta tesis queda condicionado a la aceptación de las condiciones de uso establecidas por la siguiente licencia Creative Commons: http://es.creativecommons.org/blog/licencias/ WARNING. The access to the contents of this doctoral thesis it is limited to the acceptance of the use conditions set by the following Creative Commons license: https://creativecommons.org/licenses/?lang=en Design and development of molecularly imprinted polymers and imprinted sensors Ferdia Bates Doctoral Thesis Doctoral Studies in Chemistry Director: Manel del Valle Zafra Departament de Química Facultat de Ciències 2016 Declaration Thesis submitted to aspire for the doctoral degree Ferdia Bates Director's approval: Dr. Manel de Valle Zafra Professor of Analytical Chemistry Bellaterra (Ceerdanyola del Vallès), September 2016 III Funding acknowledgement This present dissertation has been carried out in the laboratories of the Grup de Sensors i Biosensors of the Department de Química in the Universitat Autònoma de Barcelona, with the support of the Marie Curie Actions fellowship FP7-PEOPLE-2010-ITN- and the financial support of the Ministry of Economy and Innovation (MINECO) project “Electronic tongue fingerprinting: aplicaciones en el campo alimentario y de seguridad” (MCINN, CTQ2013-41577-P). Grup de Senors i Biosensors Unitat de Química Analítica Department de Química Universitat Autónoma de Barcelona Edifici Cn 08193, Bellatera IV Acknowledgments For my Masters supervisor at Cranfield university, Doctor Yi Ge, my respected colleague and friend, I would like to offer my most heart-felt thanks; without Dr Ge's encouragement, advise and reference, I most probably would not have pursued a doctorate as a career choice. I acknowledge Doctor Manel del Valle, my doctoral supervisor at the Autonomous University of Barcelona. For the lessons I have learned and the experience I have gained during our time together I extend my profound thanks. I am a better scientist because of them and I hope that the Barcelona laboratory has benefited from my time there. To Andrea and Delfina, members of MC Team Barcelona, for the support, love and understanding you both have extended to me. We have all grown so much over our shared time and PhD projects together. And now we are all doctors! To Professor Sergey Piletsky of the University of Leicester, I must also offer my sincerest gratitude for extending an invitation to work in his laboratory for several months. These resulted in a publication and a gargantuan increase in my knowledge of polymer chemistry. Even more thanks must be given for his suggestion and for originally putting me in touch with the University of Coruña which turned out to be such a fruitful collaboration. To Doctor José Manuel López-Vilariño, of the University of Coruña; his drive and charisma, not to mention his excellent taste in music, allowed this collaboration to be so productive during my time V there. A huge thank you to Maria Paredes Ramos for the great image on the front cover and also for the Spanish corrections in the resumen! To Mirko Busato of the University of Verona, I must say a very big „thank you‟ to the man who always had a clear explanation and solution to all my issues and problems with Linux and Gromacs. To Vanessa, you more than anyone have helped me to arrive to this point. Thank you and 'poof!'. To everyone who has helped and collaborated with me along this journey; if a philosophy doctorate is ultimately a search for knowledge, I hope we have found some together. VI “Sucedió, pues, que como el amor en los mozos por la mayor parte no lo es, sino apetito, el cual, como tiene por último fin el deleite, en llegando a alcanzarle se acaba, y ha de volver atrás aquello que parecía amor, porque no puede pasar adelante del término que le puso naturaleza, el cual término no le puso a lo que es verdadero amor.” “Now as love in a young man is, for the most part, nothing but appetite, and as pleasure is the ultimate end, it is terminated by enjoyment; and what seemed to be love vanishes, because it cannot pass the bounds assigned by nature; whereas true love admits of no limits.” 1 - Miguel de Cervantes Saavedra 1 Miguel de Cervantes Saavedra, in Don Quixote VII VIII Table of Contents Declaration ......................................................................................................................................... III Funding acknowledgement ................................................................................................................ IV Acknowledgments ............................................................................................................................... V Table of Contrents .............................................................................................................................. IX Abbreviations ................................................................................................................................... XV Summary ...................................................................................................................................... XXIII Resumen ...................................................................................................................................... XXVII 1. Introduction ...................................................................................................................................... 1 1.1 Molecularly Imprinted Polymers ............................................................................................... 5 1.1.1 MIP prehistory: Targeted detection and the start of the field ............................................. 5 1.1.2 The birth and growth of a discipline ................................................................................... 5 1.2. Molecular Imprinting Strategies ............................................................................................. 11 1.2.1 Covalent imprinting .......................................................................................................... 11 1.2.2 Semi-covalent imprinting .................................................................................................. 14 1.2.3 Non-covalent imprinting ................................................................................................... 18 1.3 Polymerisation formats ............................................................................................................ 23 1.3.1 Bulk form polymers .......................................................................................................... 27 1.3.2 Polymer particles and polymer resins ............................................................................... 29 1.3.3 Films, layers and membranes ............................................................................................ 37 1.4 Polymerisation mechanism ...................................................................................................... 40 1.4.1 Condensation polymerisation ............................................................................................ 41 1.4.2 Addition polymerisation ................................................................................................... 42 1.5 Rational design of a molecular imprinting protocol ................................................................ 45 XI 1.5.1 Porogenic solvents for molecular imprinting .................................................................... 46 1.5.2 Template solvation and stability ....................................................................................... 54 1.5.3 Selection of crosslinking monomer................................................................................... 56 1.5.4 Initiation rate ..................................................................................................................... 59 1.6 Transduction methods used for MIPs ...................................................................................... 62 1.6.1 MIPs in sensor arrays ........................................................................................................ 64 1.7 Computational modelling for molecular imprinting ................................................................ 68 1.7.1 Computational chemistry .................................................................................................. 70 1.7.2 Model smelliness............................................................................................................... 73 1.7.3 The combinatorial approach .............................................................................................. 76 1.8 References ................................................................................................................................ 78 2. Objectives..................................................................................................................................... 101 3. Experimental ................................................................................................................................ 105 3.1 Materials................................................................................................................................. 109 3.2 Instrumentation .....................................................................................................................
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