10-[(4-Cyanobenzylidene)]-Anthracen-9(10H)-One: syntheses, characterization and application in UV light detection

IF 2.2 4区 化学 Q2 Engineering Chemical Papers Pub Date : 2024-10-04 DOI:10.1007/s11696-024-03672-3
Gonzalo Valdivieso, Neudo Urdaneta, Bruno Pribanic, Ronald Vargas, Rafael E. Rodríguez-Lugo
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Abstract

In this work, the compound 10-[(4-cyanobenzylidene)]-anthracen-9(10H)-one (1) has been synthesized from the corresponding anthrone and 4-cyanobenzaldehyde. It has been characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (IR), high-resolution mass spectroscopy (HRMS) and single-crystal X-ray diffraction (XRD) analysis. Moreover, square wave voltammetry (SWV) was performed to determine the HOMO and LUMO potential levels of the anthrone derivative 1, which indicates that sensitization of TiO2-based electrodes is thermodynamically feasible. Therefore, this characteristic of compound 1 allowed its incorporation in a Grätzel-type solar cell. Photocurrent density measurements under UV irradiation are proportional to the light source intensity, and the operational parameters of the photoelectrochemical cell are relatively stable over time. In fact, the sensitivity of the generated photocurrent normalized by the supplied irradiance for TiO2-1 (7.73 µA/mW) as a photoanode is higher than that of TiO2 alone (5.14 µA/mW), indicating the improvement that 1 provides to TiO2 with respect to UV light detection. The higher photocurrent and the improved stability due to the implementation of 1 are very promising for possible applications as a sensitizer for UV light intensity sensors in dye-sensitized solar cells (DSSC).

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10-[(4-氰基亚苄基)]-蒽-9(10H)-1:合成、表征及在紫外光检测中的应用
本研究以相应的蒽酮和 4-氰基苯甲醛为原料合成了 10-[(4-氰基苯亚甲基)]-蒽-9(10H)-酮 (1)。通过核磁共振(NMR)、红外光谱(IR)、高分辨率质谱(HRMS)和单晶 X 射线衍射(XRD)分析对其进行了表征。此外,还通过方波伏安法(SWV)确定了蒽酮衍生物 1 的 HOMO 和 LUMO 电位水平,这表明对基于 TiO2 的电极进行敏化在热力学上是可行的。因此,化合物 1 的这一特性使其可以应用于格拉泽尔型太阳能电池。在紫外线照射下进行的光电流密度测定与光源强度成正比,而且光电化学电池的运行参数在一段时间内相对稳定。事实上,TiO2-1 作为光阳极所产生的光电流(7.73 µA/mW)的灵敏度与所提供的辐照度(5.14 µA/mW)相比更高,这表明 TiO2-1 在紫外光检测方面比 TiO2 更胜一筹。1 的光电流更高,稳定性更好,因此很有可能被用作染料敏化太阳能电池(DSSC)中紫外光强度传感器的敏化剂。
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来源期刊
Chemical Papers
Chemical Papers Chemical Engineering-General Chemical Engineering
CiteScore
3.30
自引率
4.50%
发文量
590
期刊介绍: Chemical Papers is a peer-reviewed, international journal devoted to basic and applied chemical research. It has a broad scope covering the chemical sciences, but favors interdisciplinary research and studies that bring chemistry together with other disciplines.
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