Synthesis, spectral characterization, and theoretical investigation of the photovoltaic properties of (E)-6-(4-(dimethylamino)phenyl)diazenyl)-2-octyl-benzoisoquinoline-1, 3-dione.

This research work focuses on the synthesis, characterization through spectra (FT-IR, UV-vis, and 1H-NMR) investigations, and the use of density functional theory (DFT) along with time-dependent density functional theory (TD-DFT) to investigate the electronic, structural, reactivity, photophysical properties, and the photovoltaic properties of a novel (E)-6-(4-(dimethylamino)phenyl)diazenyl)-2-octyl-benzoisoquinoline-1,3-dione. The structure of the synthesized compound was modeled using the Gaussian09W and GaussView6.0.16 softwares employing B3LYP and 6-31 + G(d) basis set. The DFT studies was performed in order to investigate the Frontier Molecular Orbital (FMO), Natural Bond Orbital (NBO), charge distribution, Nonlinear Optics (NLO), and stability of the titled molecule. The HOMO-LUMO energy gap which corresponds to the difference between HOMO and LUMO energies of the studied compound was found to be 2.806 eV indicating stiff and smooth nature of the titled molecule. This accounts for the less stability and high chemical reactivity of the compound. The photovoltaic properties were conducted to evaluate the light harvesting efficiency (LHE), short circuit current density (JSC), Gibbs free energy of injection ([Formula: see text]), open cycled voltage (VOC) and Gibbs free energy regeneration ([Formula: see text]) and solar cell conversion efficiency. Interestingly, the results obtained were found to be in good agreement with other experimental and computational findings.

Experimental and theoretical studies of the influence of alkyl groups on the photovoltaic properties of (E)-6-((2, 3-dihydroxylnaphthalene)diazenyl)-1H-benzoisoquinoline-1,3-dione-based organic solar cell.

The manipulation of the active dye material for application in dye-sensitized solar cell (DSSC) using simple or bulky group substituents is necessary for improved dye performance. Herein, we carried out a combined experimental and theoretical studies of different alkylated novel reactive (E)-6-(2,3-dihydroxyl naphthalene diazinyl)-1H-benzoisoquinoline-1,3-dione azo-based dyes using spectral (FTIR, UV-visible, and NMR) analysis and electronic structure theory method based first principle density functional theory (DFT) calculations to investigate the molecular electronic properties, structural analysis, excitation behavior, and the theoretical potential application in photovoltaic cell. The synthesized azo dye (azoD) was theoretically modeled by varying the number of alkyl chains denoted as AzoD1, AzoD2, AzoD3, and AzoD4 to represent azo dyes having ten (10), twelve (12), fourteen (14), and sixteen (16) alkyl chain length respectively. From the natural bond orbital (NBO) analysis, the higher stabilization energies, 227.80 and 227.77 kcal/mol respectively, recorded for AzoD1 and AzoD4 may be due to extra orbital contribution by π*(N21-N22) to π*C54-C56 31.19 eV for AzoD1 and π*(N21-N22) → π*(C53-C55) 31.43 eV AzoD4 confirming that chain length affected the orbital interaction of the molecules. The driving force (ΔGinject) of electron injection into the TiO2 surface (- 1.92 to - 1.93) shown in this study is indicative that alkylated azo dyes are good for improved DSSCs performance. Again, the open circuit voltage (Voc) of 1.090 (AzoD1), 1.092 (AzoD2), 1.093 (AzoD3), and 1.095 (AzoD4) are also evidence of the suitability of azo dyes as photosensitizers. All the spectroscopic analysis, FTIR, UV-visible, and NMR combined with theoretical calculations, provided accurate data for characterizing the titled azo dye compound and showed that it has good photophysical properties. The presence of alkyl groups and chain length promoted the stability of the dyes thereby making them suitable for application in DSSCs. Increase in chain length as well enhanced the electron injection into the conduction band of the semiconductor.