Rossi, Gabrio (2011) Uso della click-chemistry nella sintesi di derivati porfirinici per dispositivi fotovoltaici. [Laurea specialistica biennale]
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The aim of this study has been the synthesis, starting with tetraphenilporphyrin (TPP), of a porphyrinic dye using click-chemistry. That dye has been used as sensitizer in an organic dye Grätzel solar cell. The synthesis required the porphyrin functionalization with an alkynyl group in a three step synthetic sequence: 1) Mono-bromination of the porphyrin in ß-pyrrolic position; 2) Alkylation of the ß-pyrrolic position with a t-butylsilyl-protected alkynyl group; 3) desilanization. The azide counterpart has been obtained in two steps, starting from an aromatic amine, via diazotization followed by sodium azide substitution. At last, the target molecule has been assembled, starting with the two units as described above, via copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. The Grätzel cell prepared using the target molecule as a sensitizer, has shown very low photovoltaic efficiency value, 0.26%, and the reasons for this result will be subjects for future investigations.
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