Synthesis, molecular, electronic structure, linear and non-linear optical and phototransient properties of 8-methyl-1,2-dihydro-4H-chromeno[2,3-b]quinoline-4,6(3H)-dione (MDCQD): Experimental and DFT investigations

A A M Farag; N Roushdy; Shimaa Abdel Halim; Nasser M El-Gohary; Magdy A Ibrahim; Sara Said

doi:10.1016/j.saa.2017.10.014

Synthesis, molecular, electronic structure, linear and non-linear optical and phototransient properties of 8-methyl-1,2-dihydro-4H-chromeno[2,3-b]quinoline-4,6(3H)-dione (MDCQD): Experimental and DFT investigations

Spectrochim Acta A Mol Biomol Spectrosc. 2018 Feb 15:191:478-490. doi: 10.1016/j.saa.2017.10.014. Epub 2017 Oct 5.

Authors

A A M Farag¹, N Roushdy², Shimaa Abdel Halim³, Nasser M El-Gohary³, Magdy A Ibrahim³, Sara Said³

Affiliations

¹ Physics Department, Faculty of Science and Arts, Aljouf University, Saudi Arabia; Thin film laboratory, Physics Department, Faculty of Education, Ain Shams University, Roxy, Cairo, Egypt. Electronic address: aamfaraj@ju.edu.sa.
² Electronics Materials Dep. Advanced Technology& New Materials Research Inst., City of Scientific Research & Technological Applications (SRTA-City), New Borg El-Arab City, P.O. Box: 21934, Alexandria, Egypt.
³ Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt.

PMID: 29091907
DOI: 10.1016/j.saa.2017.10.014

Abstract

Base catalysed ring opening ring closure (RORC) reaction of 6-methylchromone-3‑carbonitrile (1) with 1,3-cyclohexanedione afforded 8-methyl-1,2-dihydro-4H-chromeno[2,3-b]quinoline-4,6(3H)-dione (MDCQD). Theoretical calculations by Density Functional Theory (DFT) at the B3LYP/6-311G (d,p) level of theory was utilized to illustrate the equilibrium geometries of MDCQD. Also, the nonlinear optical properties, simple harmonic vibrational frequencies, thermo-chemical parameters and Mullikan atomic charges were calculated. In addition, the electronic absorption spectra in polar and non polar solvents were discussed on the basis of TD-DFT calculations. A nanofiber-like structure with high aggregation was resolved by using scanning electron microscopy images and its particle sizes were measured by particle size analyzer. The spectroscopic characteristics of the prepared thin film of MDCQD were studied in a wide spectral range of 200-2500nm. The analysis of the absorption edges affords two direct optical band gaps with energies of 1.00 and 2.76eV. A characteristic emission peak of photoluminescence spectrum in the visible region was detected and has a red-shift as a result of solvent polarity. The MDCQD film based heterojunction showed rectification behavior and diode-like characteristics. The photovoltaic characteristics under illumination of 100mW/cm² were studied. The open-circuit voltage and short-circuit current were found to be 0.22V and 4.25×10^-7A/cm², respectively. Moreover, the prepared heterojunction showed remarkable phototransient characteristics which afford the probability for the operation as a photodiode.

Keywords: MO-calculation; NLO analysis; Nucleophilic reactions; Photoluminescence spectrum; Phototransient characteristics; TD-DFT theoretical investigation.