Dihydro-1H-Pyrazoles as Donor Blocks in Donor–Acceptor Chromophores for Electro-Optics: A DFT Study of Hyperpolaizability and Electronic Excitations

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Dihydro-1H-Pyrazoles as Donor Blocks in Donor–Acceptor Chromophores for Electro-Optics: A DFT Study of Hyperpolaizability and Electronic Excitations. / Ishchenko, Roman; Shelkovnikov, Vladimir.

In: International Journal of Quantum Chemistry, Vol. 124, No. 21, 04.11.2024.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{76380867159b4cdebc400277a4619a22,

title = "Dihydro-1H-Pyrazoles as Donor Blocks in Donor–Acceptor Chromophores for Electro-Optics: A DFT Study of Hyperpolaizability and Electronic Excitations",

abstract = "A diverse set of promising donors for donor–acceptor chromophores based on dihydro-1H-pyrazole (pyrazoline) for use in electro-optics was investigated using DFT at M06-2X/aug-cc-pVDZ level of theory. These calculations showed that it is possible to achieve a molecular hyperpolarizability of up to 1700*10−30 esu (up to three times higher compared to conventional diethylaniline donors) for a simple tricyanofuran-based acceptor by carefully tuning the donor structure. It was shown that the molecular hyperpolarizability is mainly affected by the substituents in the aryl rings in positions 3 and 1 of the pyrazoline cycle, while the substituents of the aryl ring in position 5 and the pyrazoline ring itself can be varied without significant effects on the hyperpolarizability. For one of the compounds, a detailed study of the lowest energy electronic excitation was performed using the TD-DFT, confirming the role of the pyrazoline ring as a secondary donor.",

keywords = "DFT calculations, donor–acceptor chromophores, electonic excitations, pyrazolines",

author = "Roman Ishchenko and Vladimir Shelkovnikov",

year = "2024",

month = nov,

day = "4",

doi = "10.1002/qua.27511",

language = "English",

volume = "124",

journal = "International Journal of Quantum Chemistry",

issn = "0020-7608",

publisher = "John Wiley and Sons Inc.",

number = "21",

}

RIS

TY - JOUR

T1 - Dihydro-1H-Pyrazoles as Donor Blocks in Donor–Acceptor Chromophores for Electro-Optics: A DFT Study of Hyperpolaizability and Electronic Excitations

AU - Ishchenko, Roman

AU - Shelkovnikov, Vladimir

PY - 2024/11/4

Y1 - 2024/11/4

N2 - A diverse set of promising donors for donor–acceptor chromophores based on dihydro-1H-pyrazole (pyrazoline) for use in electro-optics was investigated using DFT at M06-2X/aug-cc-pVDZ level of theory. These calculations showed that it is possible to achieve a molecular hyperpolarizability of up to 1700*10−30 esu (up to three times higher compared to conventional diethylaniline donors) for a simple tricyanofuran-based acceptor by carefully tuning the donor structure. It was shown that the molecular hyperpolarizability is mainly affected by the substituents in the aryl rings in positions 3 and 1 of the pyrazoline cycle, while the substituents of the aryl ring in position 5 and the pyrazoline ring itself can be varied without significant effects on the hyperpolarizability. For one of the compounds, a detailed study of the lowest energy electronic excitation was performed using the TD-DFT, confirming the role of the pyrazoline ring as a secondary donor.

AB - A diverse set of promising donors for donor–acceptor chromophores based on dihydro-1H-pyrazole (pyrazoline) for use in electro-optics was investigated using DFT at M06-2X/aug-cc-pVDZ level of theory. These calculations showed that it is possible to achieve a molecular hyperpolarizability of up to 1700*10−30 esu (up to three times higher compared to conventional diethylaniline donors) for a simple tricyanofuran-based acceptor by carefully tuning the donor structure. It was shown that the molecular hyperpolarizability is mainly affected by the substituents in the aryl rings in positions 3 and 1 of the pyrazoline cycle, while the substituents of the aryl ring in position 5 and the pyrazoline ring itself can be varied without significant effects on the hyperpolarizability. For one of the compounds, a detailed study of the lowest energy electronic excitation was performed using the TD-DFT, confirming the role of the pyrazoline ring as a secondary donor.

KW - DFT calculations

KW - donor–acceptor chromophores

KW - electonic excitations

KW - pyrazolines

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85208461669&origin=inward&txGid=be345f0ca8c87f281d50a67fc2b9e63d

UR - https://www.mendeley.com/catalogue/12ca0389-cd16-38a4-81c1-edecccfa960b/

U2 - 10.1002/qua.27511

DO - 10.1002/qua.27511

M3 - Article

VL - 124

JO - International Journal of Quantum Chemistry

JF - International Journal of Quantum Chemistry

SN - 0020-7608

IS - 21

ER -

ID: 60835181