1,2,3-Triazole-Linked Fullerene[60]-Porphyrin Dyads and Triads

Olivia Lee, New York University Michael A. Fazio, New York University David I. Schuster, New York University

Abstract According to government figures, coal currently provides about 50% of U.S. electrical generation, and the global energy consumption is expected to grow by 57% over the next 25 years. As fossil fuels are depleted in the near future, methods of acquiring renewable energy, such as solar power and wind power, must be developed not only to support the global energy demand but also to reduce air pollution. We are particularly interested in porphyrin-fullerene C60 hybrids that mimic the photosynthetic mechanisms in which sunlight can be harvested through photo-induced energy transfer reactions that lead to electron-transfer processes. This reaction system utilizes donor-acceptor (D-A) interactions, in which porphyrin is the electron donor and fullerene C60 is the electron acceptor; organic macromolecules that exhibit this property can be synthesized to facilitate the conversion of light into electrical energy. This project focuses on the synthesis of 1,2,3-triazole linkers that connect the fullerene C60 and porphyrin moieties to form macromolecules. By microwave-assisted methods, terminal alkyne, sodium azide and alkyl halide undergo Hüisgen 1,3-dipolar cycloaddition to form a triazole ring. Some of our target molecules are shown below, and these resulting molecules will be subjected to photophysical characterization. If the newly developed hybrids show potential in converting sunlight into electrical energy, there exists the possibility that photovoltaic cells with organic solar panels can be built to replace the inflexible, expensive silicon solar panels. This part of the work will be done with collaborators at other institutions, including Professor Dirk M. Guldi at the University of Erlangen in Germany and Professor Luis Echegoyen at Clemson University.

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