Abstract
•A novel 2-cyano-N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-(2-phenylhydrazono)acetamide was prepared and well-characterized.•Promising nanostructured thin film of 2-CDAPA was obtained by low-cost technique.•J–V characteristics presented notable rectifying properties.•The 2-CDAPA-based device display distinctive photosensitive characteristics.
In an attempt to explore a new category of nanostructured films for various optoelectronic field applications, a novel structure of 2-cyano-N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)-2-(2-phenylhydrazono)acetamide (CDAPA) was prepared to start with 2-aminoanthraquinone (1) and the appropriate chemical reagents. Thus, 2-aminoanthraquinone (1, 2- AAQ) condensed with 3-(2, 4-dimethyl-1H-pyrrol-1-yl)-3-oxopropanenitrile (2) to give 2-cyano-N-(9, 10-dioxo-9, 10-dihydroanthracen-2-yl) acetamide (3, 2-CDAA) which undergoes coupling reaction with the diazonium salt 5 to afford the corresponding phenylhydrazo derivative (CDAPA). Thermal evaporation under a high vacuum was utilized to obtain high-quality nanostructured films of CDAPA and fully characterizes by SEM and XRD techniques. The optical characterization using spectrophotometric methods was investigated and compared to obtain the main absorption and dispersion characteristics that affect the performance of film-based devices. The electrical characteristics of the CDAPA film-based device under the influence of dark and illumination at 100 mW/cm2 indicates good performance and remarkable sensitivity for various design and application in the field of optoelectronics.