T-grafting BODIPY-Based Photosensitizers: The Synthesis of 2,6-Diethylacrylic-8-(o-methoxyphenyl)BODIPY and Its DSSC Performance

Reinner Ishaq Lerrick (Department of Chemistry, Faculty of Science and Engineering, University of Nusa Cendana, Jl. Adi Sucipto, Penfui-Kupang 85118, NTT, Indonesia)
Wastiana Bere (Department of Chemistry, Faculty of Science and Engineering, University of Nusa Cendana, Jl. Adi Sucipto, Penfui-Kupang 85118, NTT, Indonesia)
Meliana Da Silva Braga (Department of Chemistry, Faculty of Science and Engineering, University of Nusa Cendana, Jl. Adi Sucipto, Penfui-Kupang 85118, NTT, Indonesia)
Agus Supriyanto (Department of Physics, Faculty of Mathematics and Natural Sciences, Universitas Sebelas Maret, Jl. Ir. Sutami 36A, Kentingan, Surakarta 57126, Indonesia)
Ali Hashem Essa (Department of Chemistry, College of Science, University of Basrah, Basrah 61004, Iraq)

Indonesian Journal of Chemistry
Vol 23, No 1 (2023)

A new T-grafting photosensitizer of Dye-Sensitized Solar Cell (DSSC) has been developed by aligning Donor-Acceptor (D-A) group in an axially chiral BODIPY. Synthesis of the dye was conducted over a linear approach involving one-pot, non-oxidative synthesis of 1,3,5,7-tetramethyl-8-(o-methoxyphenyl)BODIPY, bromination, and finally C2/C6 ethyl acrylate Pd-Heck coupling to produce 65% of 2-ethylacrylic-1,3,5,7-tetramethyl-8-(o-methoxyphenyl)BODIPY (BOD-8) and 35% of 2,6-diethylacrylic-1,3,5,7-tetramethyl-8-(o-methoxyphenyl)BODIPY (BOD-9), both characterized by the appearance of acrylic alkenes at 6.05, and 7.63 ppm for BOD-8, and the additional 5.43, 7.80 ppm doublet peaks for BOD-9. The resulting dye showed excellent photon harvesting-related photovoltaic properties and electronic injection and regeneration processes where the acrylic esters were found to be the Donor and the aryl was the Acceptor. Eventually, the dye produced a current at 0.5% efficiency, similar to the horizontal D-A DSSC photosensitizer design.