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Synthesis Structures and Properties of Ruthenium Piano Stool Complexes

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Synthesis Structures and Properties of Ruthenium Piano Stool Complexes Synthesis Structures and Properties of Ruthenium Piano Stool Complexes A Thesis submitted to The University of Manchester for the degree of MPhil of Philosophy in the Faculty of Science & Engineering 2016 Peng Yi School of Chemistry Contents Contents ............................................................................................................................ 2 List of Figures and Schemes ............................................................................................. 4 List of Tables ..................................................................................................................... 6 Abbreviations .................................................................................................................... 7 Abstract ............................................................................................................................. 9 Declaration ...................................................................................................................... 10 Copyright Statement ........................................................................................................ 10 Acknowledgements ......................................................................................................... 12 Chapter One Introduction ................................................................................................ 13 1.1 Background ........................................................................................................ 13 1.1.1 Molecular Nonlinear Optics (NLO) ......................................................... 13 1.1.2 Structural features .................................................................................... 15 1.1.3 Switching Nonlinear Optical Effects ....................................................... 18 1.2 β switching of C3v chromophores in LB film..................................................... 20 1.3 Project objectives ............................................................................................... 26 Chapter Two Piano-Stool Ruthenium (II) Complexes with Benzene Ring or Cymene Ring ................................................................................................................................. 27 2.1 Introduction ........................................................................................................ 27 2.2 Experimental ...................................................................................................... 29 2.2.1 Materials and Procedures ......................................................................... 29 2.2.2 General Physical Measurements .............................................................. 29 2.2.3 Syntheses .................................................................................................. 30 2.2.4 X-Ray Crystallography ............................................................................ 34 2.3 Results and Discussion ....................................................................................... 35 2.3.1 Synthetic Characterization Studies .......................................................... 35 2.3.2 1H NMR Spectroscopy Studies ................................................................ 41 2.3.3 Electronic Spectroscopy Studies .............................................................. 43 2 2.3.4 Electrochemical Studies ........................................................................... 46 2.3.5 Crystallographic Studies .......................................................................... 48 Chapter There - Piano-Stool Ruthenium (II) Complexes with HMB Ring..................... 53 3.1 Introduction ........................................................................................................ 53 3.2 Experimental ...................................................................................................... 54 3.2.1 Materials and Procedures ......................................................................... 54 3.2.2 General Physical Measurements .............................................................. 54 3.2.3 Syntheses .................................................................................................. 54 3.2.4 X-Ray Crystallography ............................................................................ 56 3.3 Results and Discussion ....................................................................................... 57 3.3.1 Synthetic Characterization Studies .......................................................... 57 3.3.2 1H NMR Spectroscopy Studies ................................................................ 59 3.3.3 Crystallographic Studies .......................................................................... 60 Chapter Four Conclusions ............................................................................................... 65 Chapter Five Future Work ............................................................................................... 66 References ....................................................................................................................... 67 Total Word Count: 15253 3 List of Figures and Schemes Fig 1. Structure of DAST ................................................................................................ 17 Fig 2. Examples of structures of C2v complexes ............................................................. 18 Fig 3. Transformation between alkynyl and vinylidene ligands ..................................... 19 Fig 4. Photocyclization reaction ...................................................................................... 20 Fig 5. Structure of subphthalocyanine ............................................................................ 21 Fig 6. Structure of triaryphosphine oxides with P=O groups .......................................... 21 Fig 7. Structure of a manganese ion with localised C3v symmetry ................................. 22 X Y Fig 8. Redox behaviors of [Ru (NH3)5L] {X= 2, 3; Y=3, 4; R= Alkyl chain} ............. 23 Fig 9. Structure of RuII compounds in LB films ............................................................. 24 Fig 10. Structure of switching RuII complex in LB films ............................................... 24 II Fig 11 Ru complexes in LB films .................................................................................. 27 6 Fig 12. Designed structure (arene = benzene η -C6H6; X= pyridine or pyridyl ligands) 28 Fig 13. Structural formulae of benzene ruthenium chloride dimer ................................. 35 Fig 14. Structural formulae of 1,3-cyclohexadiene and 1,4-cyclohexadiene .................. 36 Fig 15. Reaction for synthesis of benzene ruthenium chloride dimer............................. 36 Scheme 1. Synthesis of compounds [1-10] ..................................................................... 38 Fig 16. 1H NMR spectrum (deuterated DMSO, 400MHz, room temperature) of [Ru(Bz)(py)3][BPh4]2 ...................................................................................................... 42 Fig 17. Electronic absorption spectra of compounds 1, 2, 6, 7, 8 ................................... 44 Fig 18. Electronic absorption spectra of complexes 3, 4, 5, 9, 10 .................................. 44 Fig 19. Cyclic voltammograms of complexes 1, 2, 6, 7, 8.............................................. 47 Fig 20. Cyclic voltammograms of complexes 3, 4, 5, 9, 10............................................ 47 Fig 21. Structural representation of the complex cation in 1 .......................................... 48 Fig 22. Structural representation of the complex cation in 2 .......................................... 49 Fig 23. Structural representation of the complex cation in 11 ........................................ 49 Fig 24. Structural representation of the complex cation in 6 .......................................... 50 Scheme 2. Synthetic steps ............................................................................................... 57 4 1 Fig 25. H NMR spectrum of [Ru(HMB)(N2H4)3][BPh4]2 ............................................. 59 Fig 26. Structural representation of the complex cation in 12 ........................................ 60 Fig 27. Structural representation of the complex 17 ....................................................... 61 Fig 28. Structural representation of the complex 18 ....................................................... 62 Fig 29. Structural representation of the complex 19 ....................................................... 62 5 List of Tables Table 1. Selected 1H NMR data of complexes [1-10] ..................................................... 41 Table 2. UV-Visible data for compounds [1-10] in acetonitrilea or DCMb ..................... 43 Table 3. Electrochemical data for complexes 1, 2, 6, 7, 8 in Acetonitrile and complexes 3, 4, 5, 9, 10 in DCM. ..................................................................................................... 46 Table 4. Selected crystallographic data and refinement details for compound salts 1, 2, 6, 11 ..................................................................................................................................... 51 Table 5. Selected interatomic distances (Å) and angles (°) for compounds 1,2,11,6 ...... 52 Table 6. Selected 1H NMR data of complexes [12-16] ................................................... 59 Table 7. Selected crystallographic data
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