Photovoltaic properties of novel reactive azobenzoquinolines: experimental and theoretical investigations

Abstract

In this work, synthesis, characterization, DFT, TD-DFT study of some novel reactive azobenzoquinoline dye structures to elucidate their photovoltaic properties. The azobenzoquinoline compounds were experimentally synthesized through a series of reaction routes starting from acenaphthene to obtained aminododecylnaphthalimide and finally coupled with diazonium salts to get the desired azobenzoquinoline. Azo dye synthesized differ in the number of alkyl chains designated as (AR1, AR2, AR3, and AR4) which were experimentally analyzed using FT-IR and NMR spectroscopic methods. The synthesized structures were modelled for computational investigation using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) combined with B3LYP and 6-31+G(d) basis set level of theory. The results showed that the HOMO-LUMO energy gap was steady at approximately 2.8 eV as the alkyl chain increases, which has been proven to be within the material energy gap limit for application in photovoltaic. The highest intramolecular natural bond orbital (NBO) for the studied compounds is 27.60, 55.06, 55.06, and 55.04 kcal/mol for AR1, AR2, AR3, and AR4 respectively and the donor and acceptor interacting orbitals for the highest stabilization energy (E (2)) are LP(1)N 18 and π*C 16−O 19 respectively. The photovoltaic properties in terms of light-harvesting efficiency (LHE), Short circuit current density (J SC), Gibbs free energy of injection (ΔG inj), open-circuit voltage (V OC) and Gibbs free energy of regeneration (ΔG reg) were evaluated to be within the required limit for DSSC design. Overall, the obtained theoretical photovoltaic results were compared with other experimental and computational findings, thus, are in excellent agreement for organic solar cell design.

Detection of Carbon, Sulfur, and Nitrogen Dioxide Pollutants with a 2D Ca12O12 Nanostructured Material

“…The energy gap is fully embodied for depicting the information on the reactivity, charge transfer, electrical conductivity, and stability of a particular structure. The higher the value of energy gap exhibited by a structure, the more stable and the lower the electrical conductivity, reactivity, and charge transfer that occurs within the compound, while the lower the energy gap, the lower the stability and greater will be reactivity, electrical conductivity, and charge transfer taking place within the structure. − The results obtained from the frontier molecular orbital analysis of the studied systems are presented in Table . From the result presented in the table, the isolated Ca 12 O 12 nanocage expressed an energy gap of 4.1176 eV at the Fermi level of −3.0526.…”

Synthesis, characterization, DFT studies, and molecular modeling of hydrazinelidene‐3‐oxo‐3‐(p‐olyl) propanal derivatives as potential candidate for Hepatitis B and C treatment

“…Energy gap (E g ) which is the difference between the energy levels of HOMO and LUMO orbital is the main tool for determining the stability and reactivity of a compound. [ 31 ] According to FMO theory, an appreciating increase in the value of E g of a compound reflects less reactivity and more stability to the compound while a low E g value signifies more reactivity and less stability of the compound. As presented in table 1 and figure 1a‐b, it can be seen that compound B displayed a low energy gap value of 3.5606 eV while compound H_E exhibited a high energy gap of 3.6648 compared to H_B.…”

“…Second order perturbation energy E (2) of the compounds under study was estimated using equation . [ 31 ] …”

“…Second order perturbation energy 𝐸 (2) of the compounds under study was estimated using equation 1. [31] 𝐸 (2) = ∆𝐸 𝑖,𝑗 = −𝑞 𝑖 𝐹 2 (𝑖,𝑗) 𝜀 𝑖 −𝜀 𝑗 (1) where 𝑞 𝑖 depicts the donor occupancy, 𝜀 𝑖 and 𝜀 𝑗 represents the diagonal elements and 𝐹 (𝑖,𝑗) is the Fock matrix element.…”

First theoretical probe for efficient enhancement of optical nonlinearity via structural modifications into phenylene based D–π–A configured molecules

“…Literature survey has reported the compounds with various congurations, i.e., D-A, D-p-A, A-p-D-p-A, D-p-A-p-D, D-p-p-A, D-A-p-A, and D-D-p-A, where "D" represents the donor unit, "p" shows the p-spacer, and "A" indicates the acceptor moiety. 24 These schemes promote good agreement between the donor, p-spacer and acceptor moieties to construct a signicant push-pull mechanism and results in reduction of HOMO-LUMO E gap , 9,25,26 increase asymmetric charge scattering and bathochromic shi, hence, producing a well-known NLO response. However, extended p-conjugation, by the insertion of several electron with-drawing (EWD) endcapped moieties (-NO 2 , -CN, -Cl and -F substituents) in NFAs enhances the NLO response.…”