Ring transformation of 6-bromochromone-3-carbonitrile (1) with malononitrile dimer in basic medium furnished the unexpected (9-bromo-3-cyano-5-oxo-1,5-dihydro-2H-chromeno[4,3-b]pyridin-2-ylidene)propanedinitrile (2, BCOCPP). Density functional theory, theoretical investigation of the electronic structure, geometries linear polarizability ⟨Δα⟩ (Quadrupole moment), first-order hyperpolarizability ⟨β⟩ (Octapole moment), natural bonding orbital, molecular electrostatic potential contours, thermo-chemical parameters, harmonic vibration frequencies, the FT-IR spectrum of the compound (2, BCOCPP) in the solid phase was recorded, and time-dependent density functional theory calculations at the B3LYP/6-311G (d,p) level of theory, UV-Vis spectra, in both ethanol and dioxane solvents have been employed for compound (2, BCOCPP). The geometrical and energetic parameters have been extensively investigated to reveal the reason behind the selective formation of compound (2, BCOCPP), instead of expected product 3. The Coulomb-attenuating method-B3LYP and Corrected Linear Response Polarizable Continuum Model studied for theoretically obtaining the electronic absorption spectra in gas phase, ethanol, and dioxane, respectively, and indicate a good agreement with the observed spectra. The heterojunction based on BCOCPP showed phototransient properties under various illumination intensities that give the recommendation of the studied heterojunction in the field of optoelectronic device application.

Conflict of interest

The manuscript do not include a conflict of interest and so there is no funded entity for this research.

Supporting Information

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jhet3650-sup-0001-supplementary_data.docxWord 2007 document , 2 MB

Fig. S1. The IR spectrum of compound (2, BCOCPP)

Fig. S2. The ¹H NMR spectrum of compound (2, BCOCPP).

Fig. S3. The ¹³C NMR spectrum of compound (2, BCOCPP)

Fig. S4. The mass spectrum of compound (2, BCOCPP).

Fig. S5. Atomic charge distribution (au) for 9-bromo-3-cyano-5-oxo-1, 5-dihydro-2H-chromeno [4,3-b] pyridin-2-ylidene (2, BCOCPP) using B3LYP/6-311G (d,p).

Fig. S6. Electronic absorption spectra of (2, BCOCPP), (a) theoretical in ethanol (b) theoretical in dioxane, (c) theoretical in gas phase, (d) experimental in ethanol, (e) experimental in dioxane.

Fig. S7. Electron density contours of compound (2, BCOCPP).

Fig. S8. Correlation graphics of thermodynamic properties and temperatures of compound (2, BCOCPP).

Table S1. Second Order Perturbation Theory Analysis of Fock Matrix in NBO Basis for (9-bromo-3-cyano-5-oxo-1,5-dihydro-2H-chromeno[4,3-b]pyridin-2-ylidene) (2, BCOCPP) by B3LYP/6-311G (d,p).

Table S2. Occupancy of natural orbitals (NBOs) and hybrids of (9-bromo-3-cyano-5-oxo-1,5-dihydro-2H-chromeno[4,3-b]pyridin-2-ylidene) (2, BCOCPP) by B3LYP/6-311G (d,p).

Table S3.: Natural Charge, Natural Population and Natural electronic Configuration of (9-bromo-3-cyano-5-oxo-1,5-dihydro-2H-chromeno[4,3-b]pyridin-2-ylidene) (2, BCOCPP) by B3LYP/6-311G (d,p).

Table S4.: Total static dipol moment (μ), the mean polarizability (˂α˃) (Quadrupole moment), the anisotropy of the polarizability (Δα), and the mean first-order hyperpolarizability (˂β˃) (Octapole moment), for (9-bromo-3-cyano-5-oxo-1,5-dihydro-2H-chromeno[4,3-b]pyridin-2-ylidene) (2, BCOCPP) by B3LYP/6-311G (d,p).

Table S5.: Theoretical and experimental UV spectra of compound (2, BCOCPP) calculated at CAM-B3LYP/6–311G (d, p).

Table S6.: Thermodynamic properties at different temperatures of compound (2, BCOCPP) at B3LYP/6–311G (d, p) level of theory.

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Volume56, Issue9

September 2019

Pages 2542-2554

Synthesis, Density Functional Theory Band Structure Calculations, Optical, and Photoelectrical Characterizations of the Novel (9-Bromo-3-cyano-5-oxo-1,5-dihydro-2H-chromeno[4,3-b]pyridin-2-ylidene)propanedinitrile

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Synthesis, Density Functional Theory Band Structure Calculations, Optical, and Photoelectrical Characterizations of the Novel (9-Bromo-3-cyano-5-oxo-1,5-dihydro-2H-chromeno[4,3-b]pyridin-2-ylidene)propanedinitrile

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