Porphyrins have demonstrated promising solar conversion efficiencies in devices such as dye-sensitized and organic bulk heterojunction solar cells. The inspiration of studying porphyrins comes from natural photosynthesis where chlorins absorb light and efficiently transfer energy. Porphyrins can be tuned to enhance visible light sensitivity and their excited state energy formation can be modified to improve exciton diffusion in thin film optoelectronic devices. In this study, new porphyrin materials have been pursued to elucidate how donor-acceptor materials affect exciton diffusion. Thiazolo[5,4-d]thiazole was chosen as a strong acceptor unit and bis(2,6-dioctoxyphenyl)porphinato zinc (II), was chosen as the donor material. Thiazolothiazole (TTz) has shown high free charge carrier mobilities and is readily accessed by condensing dithiooxamide with aromatic aldehdyes. TTz materials with ethynyl groups were coupled at the meso position of the dioctoxyphenylporphyrin to ensure effective conjugation between the porphyrin donor and TTz acceptor unit. Density functional theory (DFT) modeling of the donor-acceptor system shows that the highest occupied molecular orbital (HOMO) resides on the porphyrin unit while the lowest unoccupied molecular orbital (LUMO) is centered on the thiazolothiazole unit. Presented are several synthetic strategies and spectroscopic characterizations of these new donor-acceptor porphyrin materials.

Development of porphyrin-thiazolothiazole donor-acceptor materials for solar energy conversion

251st National Meeting (2016)

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