Bogdanowicz Krzysztof Artur, Iwan Agnieszka, Dysz Karolina, Przybyl Wojciech, Marzec Monika, Cichy Kacper, Świerczek Konrad
Military Institute of Engineer Technology, Obornicka 136 Str., 50-961 Wroclaw, Poland.
Institute of Physics, Jagiellonian University, Prof. S. Lojasiewicza 11, 30-348 Krakow, Poland.
Materials (Basel). 2024 Apr 20;17(8):1909. doi: 10.3390/ma17081909.
This paper proposes molecular and supramolecular concepts for potential application in perovskite solar cells. New air-stable symmetrical imine, with thiadiazole moieties PPL2: (5E,6E)-N2,N5-bis(4-(diphenylamino)benzylidene)-1,3,4-thiadiazole-2,5-diamine), as a hole-transporting material was synthesised in a single-step reaction, starting with commercially available and relatively inexpensive reagents, resulting in a reduction in the cost of the final product compared to Spiro-OMeTAD. Moreover, camphorsulfonic acid (CSA) in both enantiomeric forms was used to change the HOMO-LUMO levels and electric properties of the investigated imine-forming complexes. Electric, optical, thermal, and structural studies of the imine and its complexes with CSA were carried out to characterise the new material. Imine and imine/CSA complexes were also characterised in depth by the proton Nuclear Magnetic Resonance H NMR method. The position of nitrogen in the thidiazole ring influences the basicity of donor centres, which results in protonation in the imine bond. Simple devices of ITO/imine (with or without CSA(-) or CSA(+))/Ag/ITO architecture were constructed, and a thermographic camera was used to find the defects in the created devices. Electric behaviour was also studied to demonstrate conductivity properties under the forward current. Finally, the electrical properties of imine and its protonated form with CSA were compared with Spiro-OMeTAD. In general, the analysis of thermal images showed a very similar response of the samples to the applied potential in terms of the homogeneity of the formed organic layer. The TGA analysis showed that the investigated imine exhibits good thermal stability in air and argon atmospheres.
本文提出了可应用于钙钛矿太阳能电池的分子和超分子概念。新型空气稳定对称亚胺，含噻二唑部分PPL2：(5E,6E)-N2,N5-双(4-(二苯胺基)亚苄基)-1,3,4-噻二唑-2,5-二胺，作为空穴传输材料，由市售且相对便宜的试剂通过一步反应合成，与Spiro-OMeTAD相比，降低了最终产品的成本。此外，两种对映体形式的樟脑磺酸(CSA)被用于改变所研究的亚胺形成配合物的HOMO-LUMO能级和电学性质。对亚胺及其与CSA的配合物进行了电学、光学、热学和结构研究以表征这种新材料。亚胺和亚胺/CSA配合物也通过质子核磁共振氢谱(H NMR)方法进行了深入表征。噻二唑环中氮的位置影响供体中心的碱性，导致亚胺键质子化。构建了ITO/亚胺(有或没有CSA(-)或CSA(+))/Ag/ITO结构的简单器件，并使用热成像相机查找所制备器件中的缺陷。还研究了电学行为以证明正向电流下的导电性能。最后，将亚胺及其与CSA的质子化形式的电学性质与Spiro-OMeTAD进行了比较。总体而言，热图像分析表明，就所形成有机层的均匀性而言，样品对施加电势的响应非常相似。热重分析(TGA)表明，所研究的亚胺在空气和氩气气氛中表现出良好的热稳定性。
