Synthesis of Ligand Containing Azulene Group by Cross Coupling and Study of Complexation with Late Transition Metals

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Mehranpoor, Nahid | 2020

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Type of Document: M.Sc. Thesis
Language: Farsi
Document No: 52801 (03)
University: Sharif University of Technology
Department: Chemistry
Advisor(s): Jamali, Sirous
Abstract:
In this study the azulene-based ligand 2-(2-pyridylazulene) has been prepared by the coupling reaction between 2-bromopyridine and 2-(2_(6methyl azulene)) -4,4,5,5 tetra methyl-1,3,2- dioxaborolane in the presence of Palladium catalyst, [PdCl2(PPh3)2] .This ligand completely characterized by one and two dimentional NMR spectroscopy and its structure determined using X-ray crystallography method. The reaction of this ligand with 0.5 equivalent of Copper (Ⅰ) or Gold (Ⅰ) metal precursors, [Cu(CH3CN)4]PF6 or [Au(SMe2)Cl] gave the mononuclear Copper (Ⅰ) complex, [Cu (2-(2-pyridyl)6-methylazulene)2]PF6, 1 or Gold (Ⅰ) complex, [Au(2-(2-pyridyl)6-methylazulene)2], 2 respectively. Complexes 1 and 2 characterized using NMR spectroscopy and ESI-Mass spectrometry. Although, complexes 1 and 2 are non-emissive both in solution and solid state, the addition of methansulfonic acid to solution of 1 and 2 in dichloromethane included a intense emission probably due to protonation of five-membered ring of azulene-based ligand
Keywords:
Coupling Reactions ; Stimuli-Responsive ; Sulfonic Acid ; Copper (I) Complexe ; Gold (I) Complex ; Azulene Based Ligand

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