ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Gonzalo Valdivieso, Neudo Urdaneta, Bruno Pribanic, Ronald Vargas, and Rafael E. Rodríguez-Lugo

Departamento de Química, Universidad Simón Bolivar, Caracas, Venezuela

E-mail: urdanet@usb.ve

Received: 23 January 2024  Accepted: 28 August 2024

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).

Keywords: Anthrone; X-ray diffraction analysis; Dye-sensitized solar cell; UV light quantification

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-024-03672-3

Chemical Papers 78 (16) 8587–8598 (2024)