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Supramolecular Polymers of Triarylamines : Studies in Aqueous Medium and Covalent Capture of Their Self-Assemblies Ting Liang

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Supramolecular Polymers of Triarylamines : Studies in Aqueous Medium and Covalent Capture of Their Self-Assemblies Ting Liang Supramolecular polymers of triarylamines : studies in aqueous medium and covalent capture of their self-assemblies Ting Liang To cite this version: Ting Liang. Supramolecular polymers of triarylamines : studies in aqueous medium and covalent capture of their self-assemblies. Organic chemistry. Université de Strasbourg, 2017. English. NNT : 2017STRAF044. tel-02003365 HAL Id: tel-02003365 https://tel.archives-ouvertes.fr/tel-02003365 Submitted on 1 Feb 2019 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. INSTITUT CHARLES SADRON UNIVERSITÉ DE STRASBOURG THÈSE présentée pour obtenir le grade de DOCTEUR de l’UNIVERSITÉ DE STRASBOURG par Ting LIANG Supramolecular Polymers of Triarylamines: Studies in Aqueous Medium and Covalent Capture of Their Self-assemblies Soutenue publiquement le 13 janvier 2017 devant le jury composé de: Docteur Olivier Colombani (SRSMC UMR 7565, Le Mans) – Rapporteur externe Professeur Patrice Woisel (CNRS UMR 8207-Universite Lille 1) – Rapporteur externe Professeur Nicolas Giuseppone (ICS, Université de Strasbourg – CNRS, Strasbourg) – Directeur de thèse Docteur Emilie Moulin (ICS– CNRS, Strasbourg) – Co-directeur de thèse Discipline : chimie organique Table of Contents ABSTRACT ........................................................................................................................................................ 3 RÉSUMÉ EN FRANÇAIS...................................................................................................................................... 5 ACKNOWLEDGEMENTS................................................................................................................................... 15 ABBREVIATIONS AND SYMBOLS ..................................................................................................................... 17 GENERAL INTRODUCTION AND OBJECTIVES ................................................................................................... 19 BIBLIOGRAPHICAL PART ................................................................................................................................. 21 CHAPTER I: GENERALITIES ON SUPRAMOLECULAR POLYMERS ......................................................................................... 23 1. Supramolecular polymers .......................................................................................................................... 23 a. Definitions ..................................................................................................................................... 23 b. Examples ....................................................................................................................................... 27 2. Characterizations of supramolecular polymers ......................................................................................... 31 3. Applications of supramolecular polymers ................................................................................................. 35 a. Self-healing materials .................................................................................................................... 35 b. Optoelectronic materials ............................................................................................................... 37 c. Biomedical applications ................................................................................................................. 39 d. Supramolecular catalysis ............................................................................................................... 41 CHAPTER II: SUPRAMOLECULAR POLYMERS IN AQUEOUS MEDIUM .................................................................................. 43 1. Hydrogen bonding supramolecular amphiphiles ....................................................................................... 43 2. π-π stacking supramolecular amphiphiles ................................................................................................. 46 3. Supramolecular amphiphiles based on host-guest interactions ................................................................ 50 4. Supramolecular amphiphilic polymers controlled by electrostatic interactions ....................................... 54 CHAPTER III: CROSS-LINKED SUPRAMOLECULAR POLYMERS ........................................................................................... 57 1. Cross-linked polymers built from ring opening metathesis polymerization (ROMP) ................................ 57 2. Cross-linked supramolecular polymers built from sol-gel processes ......................................................... 62 3. Other methods to reach cross-linked supramolecular polymers .............................................................. 66 CHAPTER IV: SUPRAMOLECULAR POLYMERS BASED ON TRIARYLAMINES ........................................................................... 71 RESULTS.......................................................................................................................................................... 81 CHAPTER V: WATER-SOLUBLE SUPRAMOLECULAR POLYMERS BASED ON TRIARYLAMINE MOTIFS ........................................... 83 1. Objectives and targeted molecules ........................................................................................................... 83 2. Synthesis and characterization of triarylamine-polyethylene glycol derivative ........................................ 84 a. Synthesis ........................................................................................................................................ 84 b. Characterizations .......................................................................................................................... 85 c. Discussion ...................................................................................................................................... 90 3. Synthesis and characterization of triarylamine-peptide derivative ........................................................... 91 a. Synthesis ........................................................................................................................................ 91 b. Characterizations .......................................................................................................................... 93 c. Discussion .................................................................................................................................... 101 4. Synthesis and characterization of triarylamine-Cy3 derivative ............................................................... 101 a. Synthesis ...................................................................................................................................... 101 b. Characterizations ........................................................................................................................ 103 c. Discussion .................................................................................................................................... 108 5. Conclusions .............................................................................................................................................. 109 CHAPTER VI: CROSS-LINKED SUPRAMOLECULAR POLYMERS BASED ON TRIARYLAMINE MOTIFS ............................................ 111 1. Objectives and targeted molecules ......................................................................................................... 111 2. Synthesis .................................................................................................................................................. 112 a. Synthesis of triarylamine-urea-siloxane derivative ...................................................................... 112 b. Synthesis of triarylamine-amide-siloxane derivative ................................................................... 112 c. Synthesis of triarylamine-norbornene derivative ........................................................................ 114 3. Characterizations ..................................................................................................................................... 114 a. Characterizations of Gel-TEOS1 and Gel-TAEOS2 ........................................................................ 114 b. Characterizations of Gel-TANBE .................................................................................................. 119 4. Conclusions .............................................................................................................................................. 133 CONCLUSIONS AND PERSPECTIVES ............................................................................................................... 135 EXPERIMENTAL PART .................................................................................................................................... 137 1. General procedures ................................................................................................................................
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