Synthesis and characterization of C60 and C70 acetylacetone monoadducts and study of their photochemical properties for potential application in solar cells

IF 0.2 Q4 CHEMISTRY, MULTIDISCIPLINARY

Revista Colombiana de Quimica Pub Date : 2021-03-25 DOI:10.15446/REV.COLOMB.QUIM.V50N1.88545

Á. Duarte-Ruiz, H. Iuele, Sergio Alejandro Torres, A. Melendez, J. Velásquez, M. Chaur, A. Duarte-Ruiz, H. Iuele, S. A. Torres-Cortés, A. Melendez, J. Velásquez, M. N. Chaur

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引用次数: 0

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.

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C60和C70乙酰丙酮单加合物的合成、表征及其光化学性质的研究

本文报道了在室温下用宾格尔反应合成C60和C70单加合物;以乙酰丙酮为配体;存在DBU(1,8-二氮杂环[5.4.0]十一-7-烯)、四溴化碳(CBr4)和邻二氯苯。二乙酰甲烷-[C60-Ih]-富勒烯-[5,6]和二乙酰甲烷-[C70-D5h]-富勒烯-[5,6]单加合物的产率分别为69%和44%。产物采用柱层析(CC，硅胶，室温下以己烷、二硫化碳和氯仿为洗脱剂)纯化，核磁共振(1H和13C)、傅里叶变换红外(FT-IR)和紫外可见光谱、基质辅助激光解吸/电离飞行时间(MALDI-TOF)质谱、循环伏安法(CV)和Osteryoung方波伏安法(OSWV)进行表征。两种化合物均表现出受扩散控制的不可逆还原峰，C60和C70单加物的LUMO能级分别为-3.09 eV、-3.13 eV。这些值与PC61BM的-3.99 eV相当。将合成的加合物掺入到倒置型钙钛矿太阳能电池中，作为电子传输材料(ETM)使用，C60和C70单加合物的功率转换效率(PCE)分别为8.5%和14.0%。当C60被较低的对称富勒烯如C70取代时，观察到可见光区的光吸收得到改善。

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来源期刊

Revista Colombiana de Quimica CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

1.50

自引率

0.00%

发文量

期刊介绍： The Revista Colombiana de Química - Colombian Journal of Chemistry (Rev. Colomb. Quim.) Is a peer-reviewed scientific journal of the Department of Chemistry, Faculty of Sciences of the Universidad Nacional de Colombia, Bogotá. It currently publishes three volumes per year: January-April, May-August and September-December. All the content published by the Journal (available online) is under a Creative Commons attribution license type BY 4.0, that allows any person or entity in the world to freely access the content, share it, download it, adapt it or make derivative works without any restriction, provided that it adequately indicates the credit to the authors and to the Colombian Journal of Chemistry.