Perylene based Metal Complexes: Their Synthesis, Electrochemical, Photovoltaic Properties and Efficient Dye Sensitized Solar Cells

This thesis approaches the perylene diimide molecules and their metal complexes, their synthesis, properties, and use in organic photovoltaics. Especially, it is focused on the use of perylene diimides as molecular organic semiconductors in dye sensitized solar cells. In the present research work, two novel chromogenic perylene diimides, N,N’bis(3amino5phenyl 2,4,6  triazinyl)perylene  3, 4, 9, 10 tetracarboxylic diimide and N,N’ bis(2 hydroxy1 (1hydroxymethyl) ethyl)perylene 3, 4, 9, 10tetracarboxylic diimide were synthesized by condensation of perylene3,4,9,10tetracarboxylic dianhydride with hindered aromatic diamine, 2,4diamino6phenyl1,3, 5triazine and aliphatic diol, 2amino1,3propanediol, respectively in isoquinoline and mcresol solvents mixture under argon atmosphere. Also a novel naphthalene diimide, N,N’ bis (3 amino5 phenyl2,4,6triazinyl) naphthalene 1, 4, 5, 8 tetracarboxylic diimide was synthesized by using same method. In order to improve the optoelectronic and photochemical properties of perylene diimides dyes, three 1,7symmetrically substituted perylene dyes, N,N’bis(2hydroxy1 (1hydroxymethyl)ethyl) 1,7 di((S)2hydroxypropoxy) perylene3,4,9,10tetracarboxylic diimide, N,N’ bis (2hydroxy 1(1 hydroxyl methyl)ethyl) 1,7di (3thiophenemethoxy) perylene3, 4, 9, 10 tetracarboxylic diimide and N,N'bis [3 ((2methyl 5 pyrimidinyl)methyl) 5 (2 hydroxyethyl) 4 methylthiazolium]  1, 7  di(2hydroxypropoxy) perylene 3, 4, 9, 10 tetracar boxylic diimide have been synthesized. In order to achieve this aim first we synthesized 1,7Dibromoperylene3,4,9,10tetracarboxylic dianhydride and then modification of perylene core at bay position was done with the different alcoholic substituents. At the end two different bay substituted perylene dianhydrides, 1,7di(3thiophenemethoxy)perylene3,4,9,10tetracarboxylic dianhydride and 1,7di((S)2hydroxypropoxy) perylene3,4,9,10 tetracarboxylic dianhydride were obtained. In order to improve the power conversion efficiencies of the products, metal complexation was studied for perylene diimides. The chemical structures of products were confirmed by using elemental analysis, IR and NMR spectroscopic measurements. Thermal stabilities of the compounds were studied with TGA and DSC measurements. Electrochemical properties were characterized by cyclic voltammetry technic. Also, photochemical properties of the compound studied by using UV−vis absorption and emission spectroscopic methods and different absorption and emission properties have been observed due to different intermolecular interactions in various solvents. Finally, the power conversion efficiencies of the compounds were successfully determined.