Synthesis Of 4H-imidazole-3-oxide Series Of New Phenoxy Nitrogen Oxides

Monomolecular organic donor-acceptor(D-A)paramagnetic systems can exhibit the bistability phenomenon in solution and be electrical conductors in the solid state,and thus have potential applications as molecular switches in the field of molecular electronics,the system is an important active electromechanical material.Stable organic groups are commonly used to act as receptor fragments for the D-A system.The migration of electron density between the donor fragment and the acceptor fragnent can be achieved by varying external factors such as light,pressure,temperature,and solvent polarity.By reviewing numerous literatures,we know that quinone methide are a conjugated structure whose structure plays an important role in changing the electronic and optical properties of conjugated systems.The use of a quinone methide as a receptor fragnent of the D-A system can increase the conductivity of the system.Therefore,the first part of this paper developed a new synthetic route for the conjugated phenoxy oxynitrides:the acyl group obtained by the acylation reaction of the commercially available thiophene derivatives,The intermediate 4H-imidazole-N-oxide is obtained by condensation of aldehydes and ketones,followed by oxidation to give the corresponding phenoxy-nitroxyl radical.The second part is a reaction of a morpholine derivative with 3-iodobenzoyl chloride to obtain a corresponding 2-hydroxyaminoketone derivative by two-step hydrolysis,followed by a condensation reaction of an aldehyde and a ketone and an oxidation reaction to obtain a desired product.Through the above synthetic route,three new types of phenoxy oxynitrides,4-bromothienyl-4H-imidazole-3-oxide,5-bromothienyl-4H-imidazole-3-oxide,and 3-iodophenyl-4H?imidazole-3-oxide were successfully synthesized,and based on this,the corresponding three types of phenoxy-nitroxyl radicals were obtained.The chemical structures of the target products and important intermediates prepared were characterized by UV,IR,1H-NMR and 13C-NMR,and their chemical structures were determined.