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Santos, E. D. A. Development of monomer-ligands from cyclic olefin for pyridine-ruthenium complexes and their polymerizations via metathesis. PhD Thesis ( Chemistry) Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, 2013. The novel monomer-ligand 3-imidepyridine-exo-7-oxabicycle[2.2.1]-hept-5-ene-2,3– dicarboxylate (oxaNBE(3imdpy)) was synthesized and characterized by elemental analysis (CHN), FTIR, X-ray diffraction and NMR ( 1 H e 13 C). It is a monodentate compound with a pyridine ligand able to be coordinated to a metal center via one side of the molecule, while the other side has a cyclic olefin that can undergo ring-opening metathesis polymerization. Additional studies were carried out using similar monomers featuring two pyridine units per molecule (oxaNBE(3amdpy)2 and NBE(3amdpy)2). It was also synthesized the monomer oxaNBE(imdPh). The compound oxaNBE(3imdpy) reacted with cis-[Ru(H2O)2(phen)2], obtained in situ from cis-[RuCl2(phen)2] in 1:1 EtOH/H2O mixture, where phen is 1,10phenanthroline, given cis-[Ru(phen)2(oxaNBE(3imdpy)2](PF6)2. This novel complex was characterized by elemental analysis (CHN), FTIR, NMR ( 1 H; 13 C; COSY; NOE), cyclic voltammetry, UV-vis spectrophotometry, quantum mechanical calculations, continuous photolysis and luminescence. The complex showed a single redox process in the cyclic voltammogram either in MeOH (E1/2 = 0.63 V) or DMF (E1/2 = 0.72 V vs Ag/AgCl) as solvent. The electronic spectra in MeOH, DMF, CH3CN, CH2Cl2 and CHCl3 showed typical absorptions of polypyridinic-ruthenium complexes in 440-500 nm range that were attributed to metal to ligand charge transfers (MLCT) from Ru(4d) to phen. The influence of the solvent on the complex behavior at room temperature as a function of time and under photolysis was studied. The UV-vis spectra showed similar spectral profiles in MeOH, CH2Cl2, CHCl3 and CH3CN, without linear clear correlations with characteristic parameters from the solvents. It was observed that the electronic spectra either in absence or presence of ambient light in MeOH, CH2Cl2 and CH3CN did not show significant spectral changes, except for CHCl3. The photolysis at 450 nm indicated changes in CHCl3 and CH2Cl2. The emission spectrum (excitation at 450 nm) of the complex did not show differences in different solvents. The monomer-ligand oxaNBE(3imdpy) and the similar monomer oxaNBE(imdPh) were polymerized in presence of ruthenium-based catalysts for 16 h at room temperature, contrary to the metal-monomer cis-[Ru(phen)2(oxaNBE(3imdpy)2](PF6)2. The monomer-ligands oxaNBE(3amdpy)2 and NBE(3amdpy)2 did not form polymers, as well as the related complex, under similar conditions.

Desenvolvimento de monômeros-ligante de olefinas cíclicas para obtenção de complexos piridínicos de rutênio e suas polimerizações via metátese