Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland.
Faculty of Physics, University of Warsaw, Pasteura 5, 02-093 Warsaw, Poland.
Molecules. 2021 Mar 12;26(6):1561. doi: 10.3390/molecules26061561.
In the present work, we report the successful synthesis and characterization of six (two new) fullerene mono- and di-pyrene derivatives based on C and C fullerenes. The synthesized compounds were characterized by spectral methods (ESI-MS, H-NMR, C-NMR, UV-Vis, FT-IR, photoluminescence and photocurrent spectroscopy). The energy of HOMO and LUMO levels and the band gaps were determined from cyclic voltammetry and compared with the theoretical values calculated according to the DFT/B3LYP/6-31G(d) and DFT/PBE/6-311G(d,p) approach for fully optimized molecular structures at the DFT/B3LYP/6-31G(d) level. Efficiency of solar cells made of PTB7: C and C fullerene pyrene derivatives were analyzed based on the determined energy levels of the HOMO and LUMO orbitals of the derivatives as well as the extensive spectral results of fullerene derivatives and their mixtures with PTB7. As a result, we found that the electronic and spectral properties, on which the efficiency of a photovoltaic cell is believed to depend, slightly changes with the number and type of pyrene substituents on the fullerene core. The efficiency of constructed solar cells largely depends on the homogeneity of the photovoltaic layer, which, in turn, is a derivative of the solubility of fullerene derivatives in the solvent used to apply these layers by spincoating.
在本工作中，我们报道了基于 C 和 C fullerene 的六个（两个新的）富勒烯单-和二-芘衍生物的成功合成和表征。通过光谱方法（ESI-MS、H-NMR、C-NMR、UV-Vis、FT-IR、光致发光和光电流谱）对合成的化合物进行了表征。通过循环伏安法确定了 HOMO 和 LUMO 能级和带隙的能量，并与根据 DFT/B3LYP/6-31G(d) 和 DFT/PBE/6-311G(d,p)方法对完全优化的分子结构在 DFT/B3LYP/6-31G(d)水平上进行理论计算的值进行了比较。根据衍生物的 HOMO 和 LUMO 轨道的确定能级以及 fullerene 衍生物及其与 PTB7 的混合物的广泛光谱结果，分析了由 PTB7：C 和 C fullerene 芘衍生物制成的太阳能电池的效率。结果发现，电子和光谱性质，据信这取决于光伏电池的效率，略微随富勒烯核心上的芘取代基的数量和类型而变化。构建的太阳能电池的效率在很大程度上取决于光伏层的均一性，而光伏层的均一性又取决于用于通过旋涂施加这些层的溶剂中富勒烯衍生物的溶解度。
