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«THESE / UNIVERSITE DE BRETAGNE-SUD présentée par Sananda NAG sous le sceau de l’Université européenne de Bretagne Préparée à LIMATB pour ...»

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THESE / UNIVERSITE DE BRETAGNE-SUD présentée par

Sananda NAG

sous le sceau de l’Université européenne de Bretagne Préparée à LIMATB

pour obtenir le titre de Etablissement de rattachement : UBS

DOCTEUR DE L’UNIVERSITE DE BRETAGNE-SUD Nom développé de l’unité : Laboratoire

Mention :

d’Ingénierie des Matériaux de Bretagne Ecole doctorale SICMA Thèse soutenue le 19th September 2014

devant le jury composé de :

Development of Conductive Prof. Jean-Francois Feller Directeur deThèse (UBS, France) Nanocomposite Sensors for Prof. Veena Choudhary Co-Directeur deThèse (IIT-Delhi, India) Anticipated Diagnostic of Dr. Mickaël Castro Co-Directeur deThèse (UBS, France) Diseases Prof. Philippe Guégan Rapporteur (UPMC Paris, France) Dr. Chris Ewels Rapporteur (Université de Nantes, France) Prof. Tristan Montier Examinateur (Université de Bretagne Occidentale, France) Nag, Sananda. Development of Conductive Nanocomposite Sensors for Anticipated Diagnostic of Diseases - 2014 Nag, Sananda. Development of Conductive Nanocomposite Sensors for Anticipated Diagnostic of Diseases - 2014 Development of Conductive Nanocomposite Sensors for Anticipated Diagnostic of Diseases A dissertation submitted in the partial fulfilment of the requirement for the degree of Doctor of Philosophy

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Acknowledgements It gives me immense pleasure and honour to thank my supervisor, Prof. Jean-Francois Feller, Head of the smart plastics group, LIMATB,UBS who helped me in climbing the rocky terrain of research during the past three years. I would like to take this opportunity to express my sincere gratitude to him for allowing me to accomplish research under his guidance and for keeping his confidence in my capabilities. He has been very supportive to me throughout my thesis with his patience and knowledge whilst allowing me the room to work in my own way. I appreciate his encouragement and enthusiasm which helped me to keep myself motivated even during the hardest times. I am deeply indebted to Prof. Jean-Francois Feller for providing me a research oriented environment along with his relentless encouragement and support.

I would like to thank my co-supervisor Prof. Veena Choudhary, Head of Centre for Polymer Science & Engineering IIT Delhi, for her efforts and direction throughout my Ph.D work.

Through her wealth of knowledge, direction and leadership I have been able to expand my knowledge in many areas of polymer science, starting from my M.Tech days in IIT-Delhi. She has always been an ideal example of passionate and inspiring mentor to me. Her scientific judgment is impeccable and she helped me to develop a scientific attitude with her sheer patience and motivation. She encouraged me to think independently and develop newer ideas regarding my research work.

I would like to deliver my sincere vote of thanks to Dr. Mickaël Castro for his guidance, cooperation and technical advices in every step to reach the goal of this thesis. His contribution in correcting this thesis is sincerely acknowledged. I would also take the opportunity to acknowledge the contribution of Prof. Philippe Guégan and his research group for successful collaborative work.

I would particularly thank jury members Prof. Philippe Guégan and Dr. Chris Ewels for devoting their valuable time to review this thesis and Prof. Tristan Montier who agreed to take part to this committee.

Nothing can be accomplished without family support. I would like to extend my special gratitude to my father Late Dr. Biplab Nag, whose memory has always been the source of my motivation even during the hardest times. I have always considered my father as my idol and even no longer with us, he remains the compass of my life. The urge to fulfil his dreams is the ultimate source of my motivation. I would like to express my deepest sense of gratitude to my mother, Mrs. Nupur Nag, without her continuous support, encouragement and endless

–  –  –

sacrifices I never would have been able to achieve my goals. Her infallible love and patience will remain my inspiration and strength throughout my life.

I owe my deepest gratitude towards my husband Suvam for his eternal support and understanding of my goals and aspirations. Without his help, I would not have been able to complete much of what I have done and become who I am. It would be ungrateful on my part if I thank him in these few words. Not only as a husband but also as my best friend and colleague he has always extended his hand of selfless supports, technical and scientific advices.

My heartfelt regards go to my father in law Mr. Sailendra Nag Chowdhury, mother in law Mrs.

Gopa Nag Chowdhury and sister in law Payel for their love and moral support.

I would like to acknowledge Dr Isabelle Pillin, Mr. Hervé Bellegou, Mr. Anthony Magueresse, Mr. Antoine Kervoelen, Mme. Francoise Péresse for their technical supports. I also appreciate the contributions of Prof. Yves Grohens, Prof. Christophe Balley, Dr. Bastien Seantier, Dr.

Stéphane Bruzaud, Dr. Alain Bourmaud, Dr. Antoine Le-Duigou for their scientific advices.

My thanks also go to my colleagues and friends Dr. Robert, Dr. Tung, Dr. Tripathi, Dr.

Vincent, Morgan, Anaelle, Nicolas, Laetitia, Dr. Saulnier, Neethu, Kishore, Aparna, David, Clara, Marine, Clement, Abdelkader and all other labmates for their timely help, and contribution to create a friendly and co-operative atmosphere in laboratory. Also I express my sincere note of thanks to everybody who has extended their helping hands towards the successful accomplishment of this thesis work, as well as expressing my apology not been able to mention all those individual names.





Finally, my greatest regards to the Almighty for bestowing upon me the courage to face the complexities of life and complete this project successfully.

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TABLE OF CONTENTS

Chapter I: Structure & content of the Thesis

I.1. General introduction & context of the thesis

I.2. Outline of the manuscript

Chapter II: Bibliographic survey

II.1. Brief note on cancer

II.2. Statistics of cancer related deaths

II.3. Conventional diagnostic tools for cancer

II.4. Interest of VOC sensing

II.5. Exhaled breath VOC biomarkers

II.6. Biomarker analysis: a noninvasive technique of cancer diagnosis................ 10 II.7. Cancer biomarkers

II.7.1. Alcohols

II.7.2. Carbonyl compounds

II.7.3. Aliphatic hydrocarbons

II.7.4. Aromatic hydrocarbons

II.8. Different methods of biomarker analysis

II.9. Electronic nose

II.10. Chemical sensors in e-nose

II.11. Smart materials

II.12. Definitions of properties related to vapour sensing

II.13. Classification of sensors

II.13.1. Chromatography

II.13.2. Electrochemical sensors

II.13.3. Mass sensitive sensors

II.13.4. Optical sensors

II.13.5. Chemoresistive sensors

II.13.5.1. Metal oxides

II.13.5.2. Conjugated polymers

II.13.5.3. Conductive polymer nanocomposite (CPC) sensors

II.14. Smart carbon nanomaterials

II.14.1. Structural aspect of carbon nanomaterials

II.14.2. Synthesis and growth

II.14.3. Carbon nanomaterials for vapour sensing applications

iv

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II.14.4. Different strategies for functionalization of carbon nanomaterial based sensing materials: State of the art

II.14.4.1. Noncovalent functionalization

II.14.4.2. Covalent functionalization

II.14.4.3. Hybridization

II.15. Safety and security: Environmental issue with carbon nanomaterials....... 39 II.15.1. Toxicity of carbon nanotubes

II.15.2. Toxicity of graphene

II.15.3. Occupational exposure limits: safe handling of toxic nanoparticles.................. 41 II.16. Conclusion and Outlook

II.17. Experimental Strategies undertaken from the light of literature survey..... 41 II.17.1. Strategy 1: Conductive oligomeric nanocomposites (COC)

II.17.2. Strategy 2: Conductive nanohybrids

II.17.3. Strategy 3: Conductive polymer nanocomposites (CPC)

Chapter III: Vapour sensing properties of cyclodextrin based conductive Nanocomposites

III.1. Introduction

III.2. Synthesis of nanocomposites and fabrication of sensors

III.2.1. Synthesis of pyrene butyric acid adamantine methyl amide

III.2.2. Synthesis of Graphene Oxide (GO)

III.2.3. Synthesis of RGO and pyrene adamantan linked RGO (RGO@PYAD)............ 49 III.2.4. Synthesis of functionalized CD wrapped RGO

III.3. Morphological characterizations of nanocomposites

III.4. Other characterizations in support of successful synthesis

III.4.1. Compositional analysis by thermo gravimetric Analysis (TGA)

III.4.2. Compositional analysis by UV-Visible spectroscopy

III.5. Vapour sensing performance of functionalized CD wrapped RGO sensors53 III.5.1. Sensitivity and selectivity of the functionalized cyclodextrin wrapped graphene based sensors

III.5.2. Functionalization of CD as a tool of tailoring selectivity of sensors.................. 57 III.5.3. Limit of detection

III.6. Vapour sensing performance of star polymer (triazole PEG) functionalizaed β-CD wrapped graphene

III.7. Conclusion

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Chapter IV: Vapour sensing properties of conductive nanohybrids

IV.1. Influence of polyhedral oligomeric silsesquioxane on the molecular selectivity of CNT based hybrid chemical vapour sensors for disease diagnosis............... 65 IV.1.1. Introduction

IV.1.2. Synthesis of nanohybrids and fabrication of sensors

IV.1.3. Characterization of the nanohybrids

IV.1.3.1. Morphological study by atomic force microscopy (AFM)

IV.1.3.2. Structural characterization by Fourier transform infra red spectroscopy.. 67 IV.1.3.3. Structural characterization by X-ray diffractogram

IV.1.3.4. Study of dispersion of CNT by UV-Visible spectroscopy

IV.1.3.5. Elemental analysis by energy dispersive X-ray spectroscopy (SEM-EDX). 69 IV.1.3.6. Compositional analysis by thermo gravimetric analysis (TGA).................. 70 IV.1.4. Dynamic vapor sensing

IV.1.5. Tailoring selectivity

IV.1.6. Limit of detection

IV.1.7. Conclusion

IV.2. Tailoring of selectivity & sensitivity of CNT / graphene based vapour sensors by grafting with fullerene

IV.2.1. Introduction

IV.2.2. Synthesis of hybrid nanomaterials

IV.2.3. Morphological study by atomic force microscopy (AFM)

IV.2.4. Morphological study by scanning electron microscopy (SEM)

IV.2.5. Compositional analysis by thermo gravimetric analysis (TGA)

IV.2.6. Dynamic Vapour sensing characterizations

IV.2.7. Limit of detection at ppb level

IV.2.8. Conclusion

Chapter V: Vapour sensing properties conductive polymer nanocomposites (CPC). 84 V.1. Introduction

V.2. Synthesis of sulfonated poly (ether ether ketone)/CNT nanocomposite vapour sensors

V.2.1. Sulfonation of Poly (ether ether ketone)

V.2.2. Fabrication of sensor

V.3. Characterizations of sulfonated Poly (ether ether ketone)

V.3.1. Determination of degree of sulfonation by nuclear magnetic resonance spectroscopy (NMR)

V.3.2. Structural characterizations by FTIR spectroscopy

V.4. Characterization of SPEEK/CNT nanocomposites

vi

–  –  –

V.4.1. Study of degradation by thermo gravimetric analysis (TGA)

V.4.2. Morphological characterization by SEM and AFM

V.4.3. Vapour sensing performance of sulfonated poly (ether ether ketone)/CNT nanocomposites

V.4.4. Influence of hybrid fillers on performance of sulfonated PEEK based CPC sensors

V.5. Conclusion

Chapter VI: Construction of electronic nose & conclusive remarks with future Prospects

VI.1. Library of sensors

VI.2. Principle component analysis

VI.3. E-Nose construction

VI.4. Discrimination of pure and binary mixture of VOC by principle component analysis (PCA)…………………………………………………………………….....105 VI.4. Conclusion and future prospects………………………………………….....107 List of Figures………………………………………………………………………………...110 List of Tables ……………………………………………………….………………………..114 Reference………………………………………………………………….……………….....115 Appendix………………………………………………………………….…………………..142 Scientific contributions ………………………………………………………………….…...157

–  –  –

Summary:

This first chapter of the thesis deals with a general introduction of the topic, explanation the problem and context of the thesis. Structure and content of the thesis is also summarized in this introductory chapter. The outline of this manuscript is briefly illustrated highlighting the focus of each chapter.

I.1. General introduction & context of the thesis Since the survival of cancer patients depends on early detection of tumour cells, developing technologies applicable for rapid detection of carcinoma is a challenge for the researchers.

Breath analyzing has emerged as a non-invasive technique for anticipated diagnosis of lung cancer, as the breath extract of lung cancer patients are found to display elevated levels of several volatile organic compounds (VOC). Clearly, the invention of a fast, reliable, economic and portable technique is highly required before breath testing becomes a clinical reality.



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