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- Title
Synthesis and characterization of C<sub>60</sub> and C<sub>70</sub> acetylacetone monoadducts and study of their photochemical properties for potential application in solar cells.
- Authors
Duarte-Ruiz, A.; Iuele, H.; Torres-Cortés, S. A.; Meléndez, A.; Velásquez, J. D.; Chaur, M. N.
- Abstract
We report on the synthesis of C60 and C70 monoadducts at room temperature through the Bingel reaction; employing acetylacetone as ligand; in presence of DBU (1,8-Diazabicyclo [5.4.0] undec-7-ene), carbon tetrabromide (CBr4), and o-dichlorobenzene. Diacetylmethane-[C60-Ih]-fullerene-[5,6] and diacetylmethane-[C70-D5h]-fullerene-[5,6] monoadducts were obtained with yields of 69% and 44%, respectively. The products were purified by column chromatography (CC, on silica gel, using hexane, carbon disulfide, and chloroform as eluents at room temperature) and characterized by Nuclear Magnetic Resonance (¹H and 13C), Fourier-Transform Infrared (FT-IR) and UV-Visible spectroscopies, Matrix-assisted Laser Desorption/Ionization-Time of Flight (MALDI-TOF) Mass spectrometry, Cyclic Voltammetry (CV), and Osteryoung Square Wave Voltammetry (OSWV). Both compounds showed irreversible reduction peaks controlled by diffusion, with LUMO energy levels of -3.09 eV, -3.13 eV for C60, and C70 monoadducts, respectively. These values are comparable with the -3.99 eV of PC61BM. The synthetized adducts were incorporated into inverted-type perovskite solar cells and were used as electron transporting materials (ETM) obtaining power conversion efficiencies (PCE) of 8.5% and 14.0% for the C60 and C70 monoadducts, respectively. When C60 is replaced by a lower symmetrical fullerene such as C70 an improved light absorption in the visible region is observed.
- Subjects
SOLAR cells; ACETYLACETONE; NUCLEAR magnetic resonance; LIGHT absorption; SILICA gel; CHLOROFORM; PHOTOVOLTAIC power systems; FULLERENES
- Publication
Revista Colombiana de Química, 2021, Vol 50, Issue 1, p86
- ISSN
0120-2804
- Publication type
Article
- DOI
10.15446/rcq.v50n1.88545