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A DFT analysis of electronic, reactivity, and NLO responses of a reactive orange dye: the role of Hartree-Fock exchange corrections

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An experimental and theoretical study based on DFT/TD-DFT approximations is presented to understand the nature of electronic excitations, reactivity, and nonlinear optical (NLO) properties of reactive orange 16 dye (RO16), an azo chromophore widely used in textile and pharmacological industries. The results show that the solvent has a considerable influence on the electronic properties of the material. According to experimental results, the absorption spectrum is formed by four intense transitions, which have been identified as \(\pi \rightarrow \pi ^{*}\) states using TD-DFT calculations. However, the TD-DFT results reveal a weak \(n\rightarrow \pi ^{*}\) in the low-lying spectral region. Continuum models of solvation indicate that these states suffer from bathochromic (ca. 15 nm) and hypsochromic shifts (ca. 4 nm), respectively. However, the expected blue shift for the absorption \(n\rightarrow \pi ^{*}\) is only described using long-range or dispersion-corrected DFT methods. RO16 is classified as a strong electrophilic system, with electrophilicity ω > 1.5 eV. Concerning the nucleophilicity parameter (N), from vacuum to solvent, the environment is active and changes the nucleophilic status from strong to moderate nucleophile (2.0 ≤ N ≤ 3.0 eV). The results also suggest that all electrical constants are strongly dependent on long-range and Hartree-Fock exchange contributions, and the absence of these interactions gives results far from reality. In particular, the results for the NLO response show that the chromophore presents a potential application in this field with a low refractive index and first hyperpolarizability ca. 214 times bigger than the value usually reported for urea (β = 0.34 × 10− 30 esu), which is a standard NLO material. Concerning the solvent effects, the results indicate that the polarizability increases \(\sim 20 \times 10^{-24}\) esu from gas to solvent while the first hyperpolarizability is calculated as \(\sim 45 \times 10^{-30}\) esu, ca. 180%, regarding the vacuum. The results suggest RO16 is a potential compound in NLO applications.

The frontier molecular orbitals, and the inverse relation between the energy-gap (Egap) and the first hyperpolarizability (β)

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Funding

Sávio Fonseca, and Regina Pereira have been supported by CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior). Lucas Modesto-Costa has been supported by FAPESPA (Fundação Amazônica de Amparo a Estudos e Pesquisas). Francisco A. O. Carvalho and Tarciso Andrade-Filho have been supported by CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico). Antônio R. da Cunha has been supported by FAPEMA (Fundação de Amparo à Pesquisa e ao Desenvolvimento Científico e Tecnológico do Maranhão) and FAPESP (Fundação de Amparo à Pesquisa do Estado de São Paulo).

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Authors and Affiliations

  1. Programa de Pós-Graduação em Química, Universidade Federal do Sul e Sudeste do Pará, Marabá, PA, 68507-590, Brazil

    Sávio Fonseca, Lucas Santos, Regina Pereira & Lucas Modesto-Costa

  2. Universidade Federal do Maranhão, UFMA, Campus Balsas, 65800-000, Maranhão, Brazil

    Antônio R. da Cunha

  3. Curso de Física,, Universidade Federal do Amapá, 68903-329, Macapá, AP, Brazil

    Marcelo R. S. Siqueira

  4. Faculdade de Química, Universidade Federal do Sul e Sudeste do Pará, Marabá, PA, 68507-590, Brazil

    Francisco A. O. Carvalho, Tarciso Andrade-Filho & Rodrigo Gester

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  1. Sávio Fonseca
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  2. Lucas Santos
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  3. Regina Pereira
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  4. Lucas Modesto-Costa
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Corresponding author

Correspondence to Rodrigo Gester.

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Supplementary information

The online version contains supplementary material available at https://doi.org/10.1007/s00894-022-05035-9.

Author contribution

Sávio Fonseca: electronic structure calculations. Lucas Santos: experimental data acquisition. Regina Pereira: experimental data acquisition. Lucas Modesto-Costa: electronic structure calculations. Antônio R. da Cunha: formal analysis, writing and original draft. Marcelo R.S. Siqueira: formal analysis, writing an original draft. Francisco A. O. Carvalho: formal analysis, writing an original draft. Tarciso Andrade-Filho: writing and original draft, writing a review and editing. Rodrigo Gester: writing an original draft, writing a review and editing, supervision.

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Fonseca, S., Santos, L., Pereira, R. et al. A DFT analysis of electronic, reactivity, and NLO responses of a reactive orange dye: the role of Hartree-Fock exchange corrections. J Mol Model 28, 85 (2022). https://doi.org/10.1007/s00894-022-05035-9

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