Sloane Evariste

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Sloane Evariste ANNÉE 2016 THÈSE / UNIVERSITÉ DE RENNES 1 sous le sceau de l’Université Bretagne Loire pour le grade de DOCTEUR DE L’UNIVERSITÉ DE RENNES 1 Mention : Chimie Ecole doctorale SDLM présentée par Sloane Evariste Préparée à l’unité de recherche (UMR 6226-CNRS) Institut des Sciences Chimiques de Rennes – Université de Rennes 1 UFR Sciences et Propriété de la Matière (SPM) Systèmes π-conjugués Thèse rapportée par : Annie-Claude Gaumont et assemblages Professeure Université de Caen / rapporteure supramoléculaires Sandrine Perruchas Chargée de recherche Ecole Polytechnique organophosphorés : Palaiseau / rapporteure synthèse et propriétés et soutenue à Rennes physico-chimiques. le 04 Octobre 2016 devant le jury composé de : Nathalie Audebrand Professeure Université de Rennes 1 / examinatrice Aude Demessence Chargée de recherche Université de Lyon 1 / examinatrice Christophe Lescop Chargé de recherche INSA Rennes / directeur de thèse Muriel Hissler Professeure Université de Rennes 1 / co-directrice de thèse ABREVIATIONS OLED : Diode électroluminescente organique (pour Organic Light-Emitting Diode) OFET : Transistor organique à effet de champs OPV : Cellules solaires organiques HO : Haute Occupée, pour l’orbitale moléculaire la plus haute occupée BV : Basse Vacante, pour l’orbitale moléculaire la plus basse vacante EQE : Rendement quantique externe (pour External Quantum Efficiency) CIE : Commission Internationale de l’Eclairage UV : Ultra-Violet λem : Longueur d’onde maximale d’émission Φ : Rendement quantique d’émission ε : Coefficient d’extinction molaire λmax : Longueur d’onde maximale d’absorption λseuil : Longueur d’onde seuil d’absorption Epa : Potentiel d’oxydation Epc : Potentiel de réduction THF : Tétrahydrofurane DCM/CH2Cl2 : Dichlorométhane Cp* : Pentaméthylcyclopentadiényl RMN : Résonance Magnétique Nucléaire δ : Déplacement chimique ppm : Parties par million s : Singulet d : Doublet t : Triplet m : Multiplet dd : Doublet de doublets td : Triplet de doublets u.a. : Unité arbitraire Ph : Phényle Me : Méthyle Et : Ethyle iPr : Isopropyle Py : Pyridyle tpy : Terpyridine dppm : Bis(diphénylphosphino)méthane dpmp : Bis(diphénylphosphinométhyl)phénylphosphine dppe : 1,2-bis(diphénylphosphino)éthane dcpm : Bis(dicyclohexylphosphino)éthane σ, π : Orbitales moléculaires sigma et pi OM : Orbitales Moléculaires TD-DFT : Théorie de la fonctionnelle de la densité dépendante du temps NIS : N-iodosuccinimide DIPA : Diisopropylamine TBAF : Fluorure de tétra-butylammonium MC : Transitions Centrées sur le Métal MLCT : Transfert de Charges du Métal vers le Ligand LLCT : Transfert de Charges de Ligand à Ligand ILCT : Transfert de Charges Intra-Ligand So : Etat singulet à l’état fondamental Sn : n Etat excité singulet Tn : n Etat excité triplet DRXP : Diffraction des Rayons X sur Poudre MEB : Microscopie Electronique à Balayage Table des matières ABREVIATIONS .................................................................................................................................. 5 INTRODUCTION GENERALE .......................................................................................................... 9 PREAMBULE .................................................................................................................................... 15 PARTIE 1 : LES SYSTEMES π-CONJUGUES A BASE DE PHOSPHOLES I. A la découverte d’un hétérocycle pas comme les autres : le phosphole ................................. 17 II. Méthodes de synthèses du cycle phosphole ........................................................................... 20 III. Intégration d’une unité phosphole dans des systèmes π-conjugués .................................... 30 Chapitre I : Développement de nouveaux systèmes π-conjugués acétyléniques à partir d’une brique 2,5-di(2-thiényl)phosphole I. Introduction ........................................................................................................................... 48 II. Synthèses ............................................................................................................................... 50 III. Caractérisation ....................................................................................................................... 51 IV. Calculs théoriques .................................................................................................................. 57 V. Fabrication de dispositifs ...................................................................................................... 60 VI. Ingénierie moléculaire : remplacement des liaisons triples par des liaisons doubles ......... 66 VII. Ingénierie moléculaire : réactivité des triples liaisons .......................................................... 71 VIII. Conclusion .............................................................................................................................. 76 IX. Experimental Part ……………………………………………………………………………………………………77 Chapitre II : Systèmes π-conjugués contenant un cycle phosphole servant de pont entre deux centres métalliques I. Introduction ........................................................................................................................... 95 II. Insertion d’un dérivé organophosphoré au sein d’un complexe de Fe(II) ........................... 96 III. Insertion d’un dérivé organophosphoré au sein d’un complexe de Pt(II) .......................... 104 IV. Insertion d’un dérivé organophosphoré au sein d’un complexe d’Au(I) ............................ 110 V. Conclusion ............................................................................................................................ 116 VI. Experimental Part ……………………………………………………………………………………………………117 PARTIE 2 : LES COMPLEXES DE Cu(I) EMISSIFS I. Introduction ............................................................................................................................. 132 II. Historique des complexes de cuivre (I) émissifs de type [Cu4I4L4] ........................................ 133 III. Les autres types de complexes de cuivre(I) émissifs .............................................................. 140 IV. Synthèse de nouveaux complexes de cuivre(I) à partir d’une approche supramoléculaire 2+ utilisant le clip bimétallique [Cu2(µ2-dppm)2(CH3CN)4] et des ligands cyanures ...................... 149 Chapitre III : Assemblages supramoléculaires composés d’ions Cu(I) liés à des ligands polyphosphines et connectés par des ligands cyanures I. Résultats préliminaires ............................................................................................................ 164 II. Assemblage supramoléculaire en forme d’hélice thermochrome en luminescence C1 utilisant le clip bimétallique [Cu2(µ2-dppm)2(CH3CN)4].(PF6)2 et le cyanure de potassium KCN .............. 167 III. Assemblage supramoléculaire luminescent en forme de « disque » C2 utilisant le clip bimétallique [Cu2(µ2-dppm)2(CH3CN)4].(PF6)2 et le cyanure de potassium KCN ........................ 175 IV. Assemblage supramoléculaire thermochrome en luminescence C3 utilisant la dpmp, le [Cu(CH3CN)4].BF4 et le cyanure de potassium KCN ...................................................................... 181 V. Conclusion ................................................................................................................................ 186 VI. Experimental Part ………………………………………………………………………………………………………187 Chapitre IV : Assemblages supramoléculaires utilisant le clip bimétallique Cu2dppm2 et des ligands organiques à fonctions nitriles terminales I. Assemblage supramoléculaire thermochrome, vapochrome et méchanochrome en luminescence C4 utilisant le clip bimétallique [Cu2(µ2-dppm)2(CH3CN)4].(PF6)2 et le 1,4- dicyanobenzène ............................................................................................................................... 196 II. Assemblage supramoléculaire thermochrome en luminescence C5 utilisant le clip bimétallique [Cu2(µ2-dppm)2(CH3CN)4].(BF4)2 et le 1,4-dicyanobenzène ................................... 209 III. Assemblage supramoléculaire luminescent C6 utilisant le clip bimétallique [Cu2(µ2- dppm)2(CH3CN)4].(PF6)2 et le ligand connecteur 1,4-phénylènediacétonitrile ............................. 218 IV. Assemblage supramoléculaire luminescent C7 utilisant le clip bimétallique [Cu2(µ2- dppm)2(CH3CN)4].(PF6)2 et le ligand connecteur aliphatique 1,6-dicyanohexane ....................... 222 V. Assemblage supramoléculaire luminescent C8 utilisant le clip bimétallique [Cu2(µ2- dppm)2(CH3CN)4].(PF6)2 et le ligand connecteur aliphatique 1,7-dicyanoheptane ..................... 226 VI. Conclusion ................................................................................................................................ 231 VII. Experimental Part ………………………………………………………………………………………………..……232 CONCLUSION GENERALE ………………………………………………………………………………………………242 INTRODUCTION GENERALE Les travaux de cette thèse consistent au développement de nouveaux matériaux π-conjugués à base de dérivés organophosphorés et sont présentés en deux parties. Dans une première partie, la synthèse, les propriétés structurales, optiques et électrochimiques, ainsi que la réactivité de différents systèmes π-conjugués à base de phospholes sont commentés ; l’objectif étant de les utiliser en tant qu’émetteurs dans des diodes électroluminescentes ou comme absorbeurs dans des cellules solaires. Dans la seconde partie, la synthèse de complexes de Cu(I) émissifs est mise en évidence par la formation d’assemblages supramoléculaires
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