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Non-Convalent Functionalization of Carbon Nanotubes : from the Organization of Surfactants to the Self-Assembly Ofporphyrins

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Non-Convalent Functionalization of Carbon Nanotubes : from the Organization of Surfactants to the Self-Assembly Ofporphyrins Non-convalent functionalization of carbon nanotubes : From the organization of surfactants to the self-assembly ofporphyrins. Geraud Delport To cite this version: Geraud Delport. Non-convalent functionalization of carbon nanotubes : From the organization of surfactants to the self-assembly ofporphyrins.. Optics / Photonic. Université Paris Saclay (COmUE), 2016. English. NNT : 2016SACLN075. tel-01505288 HAL Id: tel-01505288 https://tel.archives-ouvertes.fr/tel-01505288 Submitted on 11 Apr 2017 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. NNTè1èxBGgSACLNBzF T HESEèDEèDOCTORAT DE L’UNIVERSITE P ARIS,SACLAY PREPAREEèA L:ECOLEèNORMALEèSUPERIEUREèDEèCACHAN hECOLE NORMALE SUPERIEUREèDE PARISèSACLAY h ECOLE DOCTORALEèN°èFzx OndesèetèMatière Spécialitéèdeèdoctoratè1èNanophysique P ar M.GéraudmDELPORT Nonzconvalentmfunctionalizationmofmcarbonmnanotubes. Fromètheèorganizationèofèsurfactantsètoètheèself,assemblyèofèporphyrinsf ThèsemprésentéemetmsoutenuemàmOrsayfmlem14mdécembrem2016m:m m m CompositionmdumJurym:mè è MmeèRachelèMEALLET,RENAULTmèè ProfesseuremèPrésidenteèduèJury Mè StéphaneèBERCIAUDè mèProfesseurmèRapporteur MèTobiasèHERTELmèProfesseurmèèRapporteurè MèJean,LouisèBANTIGNIESè mèProfesseurmèExaminateur MèTalalèMALLAHèmèProfesseurmèExaminateur MèJean,SébastienèLAURETmèProfesseurmèDirecteurèdeèthèseè MèStéphaneèCAMPIDELLImèChercheurmèInvitéè MèChristopheèVOISINmèProfesseurmèInvité “Thermodynamics is a funny subject. The first time you go through it, you don’t understand it at all. The second time you go through it, you think you understand it, except for one or two small points. The third time you go through it, you know you don’t understand it, but by that time you are so used to it, so it doesn’t bother you any more.” Arnold Sommerfeld Contents Introduction 1 I Theoretical and experimental physics of carbon nanotubes and porphyrin molecules 2 1 Physical properties of single-walled carbon nanotubes . ....... 2 1.1 Basicpropertiesofcarbonnanotubes . 3 1.2 Geometricaldescription . 3 1.3 Electronicproperties ....................... 7 1.4 Opticalproperties......................... 12 1.5 Thermodynamicalgrowthconditions . 16 2 Quantum and optical properties of tetraphenylporphyrin molecules . 18 2.1 Generalities on natural dyes and chlorophyll derivatives.... 18 2.2 Structural and geometrical properties of porphyrins . .... 20 2.3 Electronicpropertiesofporphyrins . 20 2.4 Importance of the electron correlation and its optoelectronic consequences ........................... 23 2.5 Excited states relaxation of tetraphenylporphyrin . .... 24 2.6 PolarizedresponseofTPP . 25 3 Employedexperimentaltechniques . 27 3.1 Opticalabsorptionspectroscopy . 27 3.2 Photoluminescencespectroscopy. 28 3.3 TimeresolvedPhotoluminescence . 30 3.4 Anisotropymeasurement . 31 4 Fabrication of porphyrin/nanotube hybrid objects with energy trans- ferproperties ............................... 33 4.1 Functionalizationofcarbonnanotubes . 33 4.2 MicellarsuspensionofSWNTS . 37 4.3 Samplefabricationtechnique. 38 4.4 Spectroscopic monitoring of the non-covalent coupling ..... 42 5 Conclusion................................. 47 II CONTENTS II Investigation into the kinetics of the reaction and the role of the surfactant environment 48 1 Control of the different stages of the micelle swelling . ..... 49 1.1 Generalities on the organization and the dynamics timescales insurfactants ........................... 49 1.2 Designofastepbystepreaction . 53 1.3 Control of the molecule suspension in surfactants . .. 54 1.4 Comparison of the solubilization of porphyrins in sodium cholate andsodiumdodecylsulfate . 56 1.5 Study of the reaction extent using the spectroscopic evolutions 59 2 Kineticmonitoringofthereaction. 60 2.1 Samplesinfullsodiumcholate. 60 2.2 Effect of mixing of SC and SDS on a nanotube suspension . 62 2.3 Chemicalreactioninmixedenvironment . 65 2.4 InfluenceoftheSDSmicellesstability. 66 2.5 Summaryofthemicroscopicreactionmechanism . 76 3 Externalandinternaldiffusionstep . 77 3.1 Hypothesesonthereactionkineticstheory . 77 3.2 Evolution of the velocity with reactants concentrations .... 78 3.3 VelocitydifferencesamongaHiPCOsample . 82 3.4 Stacking reaction of porphyrin on graphene nanosheets . ... 84 4 Conclusion................................. 88 III Thermodynamics of the functionalization process 89 1 Thermodynamics equilibrium study on (6,5) nanotubes . .... 90 1.1 Description of the formalism to study the reaction equilibrium 90 1.2 Evidencesofacooperativestacking . 93 1.3 Evaluation of the molecular coverage of the nanotube surface. 98 1.4 Differences between the nanotube and the porphyrin spectro- scopicfeatures........................... 99 1.5 Impactofthesurfactantmixing . 107 1.6 Simulation of this two steps functionalization mechanism . 109 2 Curvaturedependenceoftheequilibrium . 114 2.1 Evolution of the thermodynamics parameter as a function of theNtdiameter.......................... 114 2.2 Physical effects at the origin of the diameter dependence . 117 2.3 Discussion on the absolute value of the Gibbs energy . 119 2.4 SortingeffectsduetoTPP/nanotubedensity . 121 2.5 Equilibriumongraphenenanosheets . 124 3 Tuning the porphyrin structure to modify the stacking ability . 129 3.1 Addingsubstituentonthephenylgroups . 129 III CONTENTS 3.2 Kinetic and thermodynamic studies in different surfactants en- vironments ............................ 131 4 Conclusion................................. 137 IV Investigation into the self assembly of porphyrins on a sp2 carbon surface 139 1 ShiftsandsplittingsoftheSoretband . 140 1.1 The Soret absorption band in carbon/TPP compounds . 140 1.2 Possible effects leading to a spectroscopic shift. 141 1.3 Experimental study of the energy splitting within the Soret band................................. 145 2 Experimental evidences and modeling of the supramolecular organi- zationprocess ............................... 154 2.1 Evidences of organization of porphyrins in the literature . .. 154 2.2 Modeling of the spectral consequences of the molecular orga- nization .............................. 157 2.3 Dipole coupling model of a linear chain of porphyrins . 162 3 Possible organization of TPP around a nanotube. 168 3.1 Geometrical characteristics from theoretical studies ...... 168 3.2 Testingtheringstructureonnanotubes . 169 3.3 Testingthehelixstructure . 173 3.4 Effect of the nanotube on the organized porphyrins . 174 4 Organizationinotherconfigurations. 180 4.1 Absorption characteristics of the porphyrin on carbon nan- otubesandgraphene . 180 4.2 Theorganizationofporphyrinsongraphene . 182 4.3 Optical spectroscopy of diphenyl porphyrins on carbon nan- otubes ............................... 190 4.4 Modeling the organization of diphenylporphyrins . 195 5 Conclusion................................. 197 Conclusion and perspectives 198 R´esum´ede la th`ese 224 IV Remerciements C’est pour moi une immense fiert´ede pouvoir terminer l’´ecriture de ce manuscrit. Cet ´enorme ouvrage, bien que non exhaustif, tente de r´esumer tous les travaux r´ealis´es pendant ces trois ann´ees de th`ese. Ce fut un travail de longue haleine, parfois solitaire mais souvent collectif. Je tenais dans ces quelques lignes `aremercier toutes les personnes qui m’ont aid´eet soutenu pendant ma th`ese. Tous d’abord, je souhaite remercier Tobias Hertel et St´ephane Berciaud de m’avoir fait l’honneur de rapporter mon travail, mais aussi Talal Mallah et Jean Louis Bantig- nies, qui ont ´et´eexaminateurs dans mon jury de th`ese. Enfin je voudrais remercier Rachel M´eallet Renaud qui a accept´ed’en ˆetre la pr´esidente et qui a fait tout son possible pour me fournir les papiers `atemps pour la qualification. Je remercie aussi Jean Fran¸cois Roch qui, en tant que directeur du laboratoire Aim´eCotton, a permis la r´ealisation de cette th`ese. Ensuite, je souhaite remercier Jean S´ebastien, qui a ´et´eun encadrant extrˆemement attentif au jour le jour. Je ne peux compter le nombre de fois o`u je suis venu te voir et o`utu m’as accueilli dans ton bureau avec patience et p´edagogie. J’ai particuli`erement appr´eci´eles discussions scientifiques que nous avons pu avoir. Je n’oublierais pas notre ”road trip” en Bavi`ere jusqu’au fin-fond d’un monast`ere pour discuter optique des nanotubes et jouer au bowling en buvant des bi`eres `ala pinte. J’ai aussi appr´eci´e d’apprendre `aenseigner la physique du solide `ates cˆot´es. Mon travail n’aurait pas signifi´egrand-chose sans les contributions de St´ephane Campidelli et de Christophe Voisin. Leur sens critique et leur exp´erience scientifique ont ´et´ed’une grande aide quand il a fallu discuter, comprendre et mettre en forme nos r´esultats. Je me souviendrais longtemps de nos longues r´eunions de travail. De mˆeme, je me dois de remercier Emmanuelle, Ga¨elle et Damien, Anne Debarre, les autres chercheurs/ing´enieurs permanents de l’´equipe Nanophotonique qui m’ont apport´eune aide pr´ecieuse. Je me dois aussi de mentionner ici tous les ´etudiants et post-doctorants qui ont contribu´e`amon travail. Sans eux le travail au laboratoire aurait ´et´emorne
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