Synthesis And Characterization Of Dithienylethylene-Based Tetraphenylporphyrin

Diarylethylene especially dithienylethylene has potential use in message storage due to its excellent thermostability and quick responsiveness. Organic optical storage material, diarylethylene can undergo reversible photocyclization between open-ring isomer and closed-ring isomer whose absorption spectra are distinguishably different under irradiation UV-Vis light, the absorption of UV-Vis light will inevitably lead to part of the photochromic reaction and destroy the previously written data. In order to prevent the problem of data damage during testing process, non-destructive optical read-out system need to be researched. Tetraphenylporphyrin has the properties of multitooth coordination effect, special macrocyclic conjugate aromatic system and strong fluorescence, through the modification of tetraphenylporphyrin, we can connect the diarylethylene unit to tetraphenylporphyrin by chemical bond or coordination bond. The contents of this paper are presented as follows:Firstly, 1,2-bis(2-methylthien-5-chloro)cyclopentene was synthesized through chlorination, Dione addition and self shrinking cyclization reaction by using 2-methylthiophene as starting material, and then reacted with bromide pyridine hydrochloride through Suzuki coupling, each step of the product structure is verified by MS,’H-NMR. The photochromic properties were investigated by UV-Vis spectroscopy.Secondly, we designed and synthesized the symmetric pyridyl dithienylethylene in a new synthetic route via Suzuki coupling, Friedel-Crafts acylation and McMurry coupling by using 2-methylthiophene as starting material. The photochromic properties of the target compound and its interaction with Ni2+, Sn2+ were also investigated by UV-Vis spectroscopy and fluorescent emission spectroscopy.Thirdly, synthesis and characterization of tetraphenylporphyrin via pyrrol and benzaldehyde as starting material, salicylic acid as protonation and xylene as solvent, DMSO was added as desiccant. Tetraphenylporphyrin was coordinated with metal ion.Lastly, The complexes were coordinated with bisthienylethylene with pyridine and the influences of different solvents on synthesis were studied. The optical properties were tested.