Theoretical investigation on the functional group modulation of UV-Vis absorption profiles of triphenylamine derivatives

Gong, Kun; Xu, Fangfang; Zhang, Zhao; Li, Wei; Liu, Dongzhi; Zhou, Xueqin; Wang, Lichang

doi:10.1039/d3cp01630g

Cited by 3 publications

(2 citation statements)

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“…69 For organic small molecules of larger size, many conformers may coexist and molecular dynamics simulations may be needed to ensure proper sampling of the conformational configuration. 70 Three types of DFT calculations were performed for each molecule in a specific solvent environment, namely, geometry optimizations, harmonic frequency calculations, and anharmonic frequency calculations. Two solvents, NNDMA (N,Ndimethylacetamide) and tetrahydrofuran (THF), were used to understand the solvent effects on FRs.…”

Section: Computational Detailsmentioning

confidence: 99%

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Effects of the Intramolecular Group and Solvent on Vibrational Coupling Modes and Strengths of Fermi Resonances in Aryl Azides: A DFT Study of 4-Azidotoluene and 4-Azido-N-phenylmaleimide

Perera,

Aikawa,

Shaner

et al. 2023

J. Phys. Chem. A

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The high transition dipole strength of the azide asymmetric stretch makes aryl azides good candidates as vibrational probes (VPs). However, aryl azides have complex absorption profiles due to Fermi resonances (FRs). Understanding the origin and the vibrational modes involved in FRs of aryl azides is critically important toward developing them as VPs for studies of protein structures and structural changes in response to their surroundings. As such, we studied vibrational couplings in 4-azidotoluene and 4-azido-N-phenylmaleimide in two solvents, N,N-dimethylacetamide and tetrahydrofuran, to explore the origin and the effects of intramolecular group and solvent on the FRs of aryl azides using density functional theory (DFT) calculations with the B3LYP functional and seven basis sets, 6-31G(d,p), 6-31+G(d,p), 6-31++G(d,p), 6-311G(d,p), 6-311+G(d,p), 6-311++G(d,p), and 6-311++G(df,pd). Two combination bands consisting of the azide symmetric stretch and another mode form strong FRs with the azide asymmetric stretch for both molecules. The FR profile was altered by replacing the methyl group with maleimide. Solvents change the relative peak position and intensity more significantly for 4-azido-N-phenylmaleimide, which makes it a more sensitive VP. Furthermore, the DFT results indicate that a comparison among the results from different basis sets can be used as a means to predict more reliable vibrational spectra.

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Section: Computational Detailsmentioning

confidence: 99%

“…This conformer is energetically the same as the second conformer . For organic small molecules of larger size, many conformers may coexist and molecular dynamics simulations may be needed to ensure proper sampling of the conformational configuration …”

Section: Computational Detailsmentioning

confidence: 99%

Effects of the Intramolecular Group and Solvent on Vibrational Coupling Modes and Strengths of Fermi Resonances in Aryl Azides: A DFT Study of 4-Azidotoluene and 4-Azido-N-phenylmaleimide

Perera,

Aikawa,

Shaner

et al. 2023

J. Phys. Chem. A

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The molecular structure and spectra of diphenylmethane under the external electric field

Zhang,

Feng,

Niu

et al. 2024

Chemical Physics Letters

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Structure–property relationships in fluorescence of carbon dots from premixed ethylene flames

Shen,

Zhou,

Shao

et al. 2024

Proceedings of the Combustion Institute

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Theoretical investigation on the functional group modulation of UV-Vis absorption profiles of triphenylamine derivatives

Abstract: Understanding functional group modulation of electronic structure and excitation is pivotal to the design of organic small molecules (OSMs) for photoelectric applications. In this work, we employed density functional theory...

Cited by 3 publications

References 74 publications

Effects of the Intramolecular Group and Solvent on Vibrational Coupling Modes and Strengths of Fermi Resonances in Aryl Azides: A DFT Study of 4-Azidotoluene and 4-Azido-N-phenylmaleimide

Effects of the Intramolecular Group and Solvent on Vibrational Coupling Modes and Strengths of Fermi Resonances in Aryl Azides: A DFT Study of 4-Azidotoluene and 4-Azido-N-phenylmaleimide

The molecular structure and spectra of diphenylmethane under the external electric field

Structure–property relationships in fluorescence of carbon dots from premixed ethylene flames

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