Synthesis and characterization of C60 and C70 acetylacetone monoadducts and study of their photochemical properties for potential application in solar cells
| Autor: | A. Duarte-Ruiz, M. N. Chaur, Sergio Alejandro Torres, Helena Iuele, A. Meléndez, Álvaro Duarte-Ruiz, J. D. Velásquez, Jose D. Velasquez, H. Iuele, S. A. Torres-Cortés, Angie Melendez, Manuel N. Chaur |
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| Rok vydání: | 2021 |
| Předmět: |
Carbon disulfide
Chloroform Fullerene Chemistry Silica gel Acetylacetone Analytical chemistry 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Bingel reaction Cyclic voltammetry 0210 nano-technology HOMO/LUMO |
| Zdroj: | Revista Colombiana de Química. 50:86-97 |
| ISSN: | 2357-3791 0120-2804 |
| DOI: | 10.15446/rev.colomb.quim.v50n1.88545 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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