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Electrochemical and Spectroelectrochemical Characterisation of Cyano and Trifluoromethyl

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Electrochemical and Spectroelectrochemical Characterisation of Cyano and Trifluoromethyl Electrochemical and Spectroelectrochemical characterisation of cyano and trifluoromethyl substituted polypyridines and their transition metal complexes Alexander R. L. Delf Thesis submitted for the degree of Ph.D. The University of Edinburgh May 2011 Declaration I hereby declare that this thesis has been entirely composed by myself and that the work described herein is my own except where clearly mentioned either in acknowledgement, reference or text. It has not been submitted in whole or in part for any other degree, diploma or other qualification. Alexander R. L. Delf May 2011 i Acknowledgments First and foremost I would like to thank Prof. Lesley Yellowlees for all of her help, advice, enthusiasm and bars of Swiss chocolate that she has given me during my time with “the lab rats”. But most of all I would like to thank her for believing in me when even I didn’t. Thanks have to go to Prof. Eric Mcinnes for the solid phase EPR simulations. I’d also like to thank the University of Edinburgh crystallography service for the crystal structures. For their help with NMR, Mass Spectrometry and CHN analysis thanks must go to Marika DeCremoux, Alan Talyor and Sylvia Williamson respectively. A special thank you has to go to Dr. Patricia Richardson of the EAsT Chem Research Computing Facility for her all her help and advice on all things computational and for long rambling discussions about interesting aspects of spectroscopy. For helpful discussions about the finer points of electrochemistry I’d like to thank Dr. Andy Mount, Dr. John Henry and Charlotte Brady. Thanks must also go to Dr. Neil Robertson for helping me with my work in those times when Lesley was away from the department. Thanks to all the members of the Yellowlees “lab rats” over the years; Dr. Lucy Moorcaft, Dr. Salma Al-Musharafi, Ed Nind, Calum Findlay and last but no means least Dr. Paul Murray. Thanks Paul for teaching me the tricks of the trade and letting me take part in some of the Chemical Connections fun. ii A thank you of the lab friends wouldn’t be complete without mentioning the Robertson group. The “solar girls” Dr. Keri McCall, Dr Charlotte Linfoot, Martina “bella” Congiu, Nina Chadwick and Tracy Hewat. The “materials boys” Dr. Rob Valentine, Dr. Simon Dalgleish, Dr Luca Pilia, Max “Maximus” Reinhardt and Alex Whyte. Thanks for all the banter and assorted baked goods, especially after you left me for pastures new down the corridor. I must single out Nina for special thanks here for managing to get the crystal structure of the 4,4´-(CF 3)2-bpy ligand while doing her Masters project with Yellowlees group. Don’t worry your name will go the paper once it’s done. Now to thank the people from outside the chemistry department that have had a hand in creation of my magnum opus. A huge thanks has to go the Kendo club boys in the Hill Square flat for all the nights that they have let me stay on their couch while I was writing up. Also the stress reliving value of getting to beat someone round the head with a bamboo stick cannot be overstated. Finally I must thank my mum for putting up with me over the last few months while I have been writing up. Thank you for the free food, accommodation and for bank rolling my trips back to Edinburgh. I’ll get started on that long list of odd jobs you want done next week. iii Abstract This thesis is concerned with the electrochemical and spectroelectrochemical characterisation of cyano (CN) and trifluoromethyl (CF 3) substituted polypyridine ligands and their metal complexes. The ligands investigated were X-CN-py (X = 3, 4 and 5, py = pyridine), X,X´-(CN) 2-bpy) (X,X´ = 3,3´, 4,4´ and 5,5´ bpy = 2,2´- bipyridine) and X,X´-(CF 3)2-bpy (X,X´ = 3,3´, 4,4´ and 5,5´). The Pt(II) complexes of the X-CN-py and X,X´-(CN) 2-bpy ligands were studied along with the Fe(II) complexes of the X,X´-(CN) 2-bpy and X,X´-(CF 3)2-bpy ligands. Electrochemical studies of the X-CN-py ligands indicated that 2-CN-py and 4-CN-py have one reversible 1e - reduction and 3-CN-py has one quasi-reversible reduction. 4-CN-py is more easily reduced than 2-CN-py. EPR experiments on [2-CN-py] 1- and [4-CN-py] 1- combined with DFT calculations have indicated that the semi-occupied molecular orbital (SOMO) is delocalised over the entire molecule. The complex - [Pt(4-CN-py) 2Cl 2] undergoes two reversible 1e reductions, attributed to the sequential reduction of the two 4-CN-py ligands. [Pt(3-CN-py) 2Cl 2] was found to exhibit one irreversible reduction. The electrochemistry of the X,X´-(CN) 2-bpy ligands indicated that 3,3´-(CN) 2-bpy - and 5,5´-(CN) 2-bpy have two reversible 1e reductions while 4,4´-(CN) 2-bpy has only - one reversible 1e reduction. The reductions of 5,5´-(CN) 2-bpy occur at significantly less negative potentials than those in 3,3´ or 4,4´ analogue. In-situ UV/Vis/NIR and EPR experiments on the X,X´-(CN) 2-bpy ligands indicate that the reduction electron is delocalised over both the CN-py rings with the SOMO being spread across the entire molecule. [Pt(3,3´-(CN) 2-bpy)Cl 2] and [Pt(5,5´-(CN) 2-bpy)Cl 2] undergo two iv - reversible 1e reductions, attributed to the sequential reduction of the X,X´-(CN) 2-bpy ligand. 4,4´-(CF 3)2-bpy and 5,5´-(CF 3)2-bpy, whose X-ray crystallographically determined - structures are reported, both have one reversible 1e reduction while 3,3´-(CF 3)2-bpy exhibits an irreversible reduction. Again the 5,5´ analogue is the most easily reduced. Spectroelectrochemical results indicate that the reduction electron enters a SOMO that is delocalised over both the CF3-py rings. Substitution in the 5,5´ positions is determined to be electronically most significant. Complexes of the general formula [Fe(II)(X 2-bpy) 3][BF 4] (where X = CN or CF 3 in the 4,4´ or 5,5´ positions) exhibit three reversible ligand based reduction processes and a metal based oxidation. UV/Vis/NIR and EPR studies have confirmed that the reduction electron in each case enters a molecular orbital that is predominantly based on a bpy ligand. - The redox potentials of 4-CN-py and 5,5´-(CN) 2-bpy are solvent dependent with 1e - reduction of 4-CN-py and the two 1e reductions of 5,5´-(CN) 2-bpy moving to less negative potentials as the acceptor number (AN) of the solvent increases. A computational model has been developed for the study of the electronic properties of substituted bipyridines using DFT methods. This model has been used to aid the analysis of the EPR and UV/Vis/NIR spectra of the X2-bpys studied. v Contents Declaration i Acknowledgments ii Abstract iv Contents vi Abbreviations x 1. Introduction 1 1.1 2,2´-bipyridine 1 1.2 Substituted 2,2´-bipyridine 7 1.3 Previous investigations into solvent effects 28 1.4 2,2´-bipyridine as a ligand for TM complexes 32 1.5 The aims of this thesis 34 1.6 References 37 2. Experimental and Theoretical techniques 43 2.1 Synthesis 43 + - 2.1.1. [TBA] [BF 4] electrolyte 43 2.1.2. 5,5´-dibromo-2,2´-bipyridine 43 2.1.3. 5,5´-dicyano-2,2´-bipyridine 43 2.1.4. 4,4´-trifluromethyl-2,2´-bipyridine 44 2.1.5. 5,5´-trifluromethyl-2,2´-bipyridine 45 2.1.6. 3,3´-trifluromethyl-2,2´-bipyridine 46 2.1.7. [Pt(II)(4-cyanopyridine) 2(Cl) 2] 46 2.1.8. [Pt(II)(3-cyanopyridine) 2(Cl) 2] 46 2.1.9. [Pt(II)(3,3´-dicyano-2,2´-bipyridine)(Cl) 2] 47 2.1.10. [Pt(II)(5,5´-dicyano-2,2´-bipyridine)(Cl) 2] 47 2.1.11. [Fe(II) (5,5´-dicyano-2,2´-bipyridine) 3][BF 4]2 48 2.1.12. [Fe(II) (4,4´-ditrifluoromethyl-2,2´-bipyridine) 3][BF 4]2 48 2.1.13. [Fe(II) (5,5´-ditrifluoromethyl-2,2´-bipyridine) 3][BF 4]2 49 2.1.14. Purification of solvents 49 2.1.15. Purchased Compounds 50 2.2 Electrochemical Techniques 50 2.2.1. Cyclic Voltammatory 52 vi 2.2.2. Differential Pulse Voltammetry 56 2.3 Spectroelectrochemcical Techniques 60 2.3.1. Ultra Violet/Visible/Near Infra-Red spectroelectrochemistry 62 2.3.2. Electron Paramagnetic Resonance Spectroscopy 64 2.4 Computational Methods 73 2.4.1. Fundamental Theory 73 2.4.2. Hartree-Fock 76 2.4.3. Density Functional Theory 77 2.4.4. Self-Consistent Field method 79 2.4.5. Choice of Basis Set 81 2.4.6. Time-dependent density functional theory 84 2.4.7. Solvent Models 85 2.4.8. Development of computational model for EPR analysis 85 2.4.9. TD-DFT for UV/Vis/NIR spectroelectrochemistry analysis 93 2.5 References 96 3. Electrochemical and Spectroelectrochemical characterisation of 2-CN-py, 3-CN-py and 4-CN-py and their Pt complexes 99 3.1 Introduction 99 3.2 Electrochemistry 102 3.2.1. Cyanopyridines 102 3.2.1.1. Cyclic Voltammetry 102 3.2.1.2. Differential Pulse Voltammetry 105 3.2.2. [Pt(X-CN-py) 2Cl 2] complexes 107 3.2.2.1.
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