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Organizations in Supramolecular Polymers: from the Solution to the Bulk Behavior Jessalyn Cortese

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Organizations in Supramolecular Polymers: from the Solution to the Bulk Behavior Jessalyn Cortese Organizations in supramolecular polymers: from the solution to the bulk behavior Jessalyn Cortese To cite this version: Jessalyn Cortese. Organizations in supramolecular polymers: from the solution to the bulk behavior. Polymers. Université Pierre et Marie Curie - Paris VI, 2013. English. pastel-00813603 HAL Id: pastel-00813603 https://pastel.archives-ouvertes.fr/pastel-00813603 Submitted on 15 Apr 2013 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. A BCDEFFFAFDF ABCDEDB !!"!# AFBFDEBDBDD D!CDEFF$FAFDF DDCD %#&##!'&!('&!)!* )&'&##&!&#)&'&## CFDEDD DEDBF FCD !"#$%#&'(#&) *BDDBDCD ! D+FBEED,-#'./0'12,3'+ +F/*BDBDDCD ! D(DBEDD+41)#&-5 )FBBD !"6DE/7BE8FC#-90 )FBDB ! D!E/4#' &: EBD !"&";"<(DB=!&'6&) ABCDEB Table of contents Table of contents Organizations in supramolecular polymers: from the solution to the bulk behavior Introduction...............................................................................................7 Acronyms and Abbreviations..................................................................11 Chapter I. From polymers and supramolecular chemistry to supramolecular polymers........................................................................13 1. Polymers.................................................................................................................17 2. Supramolecular chemistry.......................................................................................23 3. Supramolecular polymers.......................................................................................29 Chapter II. Synthesis of supramolecular polymers by grafting of Thy and DAT stickers on telechelic PPO chains...................................................55 1. Telechelic PPO chains as spacers between the stickers........................................59 2. Grafting DAT sticker...............................................................................................65 3. Grafting Thy sticker................................................................................................68 4. Blending ThyPPO-XThy with DATPPO-XDAT...................................................77 5. Heteroditopic grafting of Thy and DAT (grafting Thy on one side and DAT on the other side)...................................................................................................................78 Chapter III. Supramolecular polymers in solution: solvent dependent behavior..................................................................................................91 1. Supramolecular polymers in solution......................................................................95 2. Supramolecular polymers act as bolaamphiphiles in a dissociative solvent.........105 3. Supramolecular polymers are associated in a nondissociative solvent...............109 4. Conclusions and perspectives..............................................................................139 Chapter IV. Order and disorder in bulk supramolecular polymers........143 1. Orderdisorder transition in supramolecular polymers..........................................147 2. Disorder in supramolecular polymers....................................................................172 3. Suppression of mesoscopic order by complementary interactions in supramolecular polymers....................................................................................................................177 3 Table of contents Chapter V. Glass transition of supramolecular polymers in the bulk....189 General Conclusion...............................................................................201 Appendix I. Material and methods........................................................203 Appendix II. Synthesis and characterization.........................................207 Appendix III. Résumé en français.........................................................237 Acknowledgements...............................................................................247 4 Table des matières Table des matières Organisations dans les polymères supramoléculaires : du comportement en solution au comportement en masse Introduction...............................................................................................7 Acronymes et Abbréviations...................................................................11 Chapitre I. Des polymères et de la chimie supramoléculaire vers les polymères supramoléculaires.................................................................13 1. Polymères...............................................................................................................17 2. Chimie supramoléculaire.........................................................................................23 3. Polymères supramoléculaires.................................................................................29 Chapitre II. Synthèse de polymères supramoléculaires par greffage de Thy et DAT sur chaînes PPO..................................................................55 1. Chaines PPO téléchelique comme espaceurs entre les motifs collants.................59 2. Greffage du motif DAT............................................................................................65 3. Greffage du motif Thy.............................................................................................68 4. Mélange de ThyPPO-XThy et DATPPO-XDAT..................................................77 5. Greffage hétéroditopique de Thy et DAT (Thy dun côté et DAT de lautre)...........78 Chapitre III. Polymères supramoléculaires en solution : comportement dépendant du solvant..............................................................................91 1. Polymères supramoléculaires en solution...............................................................95 2. Polymères supramoléculaires se comportant comme des bolaamphiphiles dans un solvant dissociant......................................................................................................105 3. Polymères supramoléculaires associés en solvants nondissociants...................109 4. Conclusions et perspectives.................................................................................139 Chapitre IV. Ordre et désordre dans les polymères supramoléculaires en masse....................................................................................................143 1. Transition ordredésordre dans les polymères supramoléculaires.......................147 2. Désordre dans les polymères supramoléculaires.................................................172 3. Suppression de lordre mésoscopiqie par interactions complémentaires dans les polymères supramoléculaires...................................................................................177 5 Table des matières Chapitre V. Transition vitreuse dans les polymères supramoléculaires and masse ...189 Conclusion générale.............................................................................201 Annexe I. Matériel et méthodes............................................................203 Annexe II. Synthèses et caractérisation................................................207 Annexe III. Résumé en français............................................................237 Remerciements.....................................................................................247 6 Introduction Introduction Supramolecular chemistry (the chemistry of noncovalent bonds) is a powerful tool to create new functional materials.1 Indeed, since noncovalent interactions are reversible and sensitive to their environment, supramolecular materials can display stimuliresponsive characteristics, such as their size, rheology and viscoelasticity. Therefore, unlike high molecularweight covalent polymers, their processing and recycling can be easily achieved. Furthermore, incorporating noncovalent bonds into materials can impart original properties, such as selfhealing. As a matter of fact, selfhealing and thermoreversible rubbers from supramolecular assembly were developed in the Soft Matter and Chemistry Laboratory.2 In these selfhealing elastomers, hydrogen bonds between small molecules allow them to selfassemble into threedimensional networks reminiscent of reticulated polymers.2 The associations involved are weak but numerous. The unique properties of these materials may be strongly influenced by its suspected nanostructuration, arising from a segregation between the polar hydrogen bonding groups (the stickers) and the apolar linkers between these groups (the spacers).3,4 Indeed, phase segregation can facilitate hydrogen bonding by locally increasing the sticker concentration.5 Furthermore, nanodomains are associated with slow diffusion processes, as in block copolymers,6 and play a part in the healing after damage which implies a reconstruction of the nanostructure.3,4 1 Steed, J. W.; Atwood, J. L.; Supramolecular chemistry, 2nd Edition; Wiley: Chippenham, UK, 2009. 2 Cordier, P.; Tournhilhac, F.; SouliéZiakovic, C.;
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