Computational design of <i>p</i>-(dimethylamino)benzylidene-derived push–pull polyenes with high first-hyperpolarizabilities

Liu, Yidan; Yuan, Yongbo; Tian, Xiaohui; Yuan, Jianyong; Sun, Jinyu

doi:10.1039/c9cp05631a

Cited by 8 publications

(9 citation statements)

References 60 publications

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“…TCF12 and TCF13), consistent with the results reported in the literature. [75] Indeed, these two dyes exhibit the largest oscillator strengths, resulting from the increase of the backbone length.…”

Section: Optical Propertiesmentioning

confidence: 99%

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

et al. 2021

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A series of chromophores was designed and synthesized using 2-(3-cyano-4,5,5-trimethylfuran-2 (5H) -ylidene) malononitrile (TCF) as the electron acceptor and differing from each other by the use of thirteen different electron donors. The different dyes were characterized for their optical and electrochemical properties and theoretical calculations were also carried out to support the experimental results. By changing the electron donor in the thirteen dyes, chromophores absorbing between 430 nm and 700 nm could be synthesized. Solvatochromism of the different dyes was analyzed in 23 solvents of different polarity and a positive solvatochromism was determined for all chromophores using the semi-empirical solvent polarity scales based on the Kamlet-Taft parameters (π *) or the Catalan parameters (SdP and SPP).

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Section: Optical Propertiesmentioning

confidence: 99%

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

et al. 2021

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“…Additionally, the time-dependent DFT (TDDFT) was utilized for the excited states (S 1 and T 1 ). The fluorescence emission wavelengths of TCO–DMAC and PhCO–DMAC were calculated using different functionals, including B3LYP, PBE0, M06, PBE33, PBE38, BMK, M062X, CAM-B3LYP, LC-PBE, and ωB97X-D, − as shown in Table S1. All calculations were performed by using the 6-311G** basis set.…”

Section: Methodsmentioning

confidence: 99%

Enhancing Reverse Intersystem Crossing in Triptycene-TADF Emitters: Theoretical Insights into Reorganization Energy and Heavy Atom Effects

Lv,

Song,

et al. 2024

J. Phys. Chem. A

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Thermally activated delayed fluorescence (TADF) emitters based on the triptycene skeleton demonstrate exceptional performance, superior stability, and low efficiency roll-off. Understanding the interplay between the luminescent properties of triptycene-TADF molecules and their assembly environments, along with their excited-state characteristics, necessitates a comprehensive theoretical exploration. Herein, we predict the photophysical properties of triptycene-TADF molecules in a thin film environment using the quantum mechanics/molecular mechanics method and quantify their substantial dependency on the heavy atom effects and reorganization energies using the Marcus−Levich theory. Our calculated photophysical properties for two recently reported molecules closely align with experimental values. We design three novel triptycene-TADF molecules by incorporating chalcogen elements (O, S, and Se) to modify the acceptor units. These newly designed molecules exhibit reduced reorganization energies and enhanced reverse intersystem crossing (RISC) rates. The heavy atom effect amplifies spin−orbit coupling, thereby facilitating the RISC process, particularly at a remarkably high rate of ∼10 9 s −1 .

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“…Simulations for the isolated molecular properties of all designed HTMs were performed by employing density functional theory (DFT) [74][75][76] and time-dependent TD-DFT, 77,78 based on Gaussian 09 [79][80][81] and Multiwfn 82 software. The DFT combined with the B3LYP [83][84][85] functional was used to optimize the ground and ionic state geometries of all molecules, and subsequently the TD-DFT associated with the PBE38 86,87 functional was applied to investigate the optical properties of the HTMs. The simulations were completed in the 6-31G(d, p) basis set, and the solution environment was the dichloromethane (DCM) solution with the solvent effect of the PCM model.…”

Section: Theoretical Methods and Computational Detailsmentioning

confidence: 99%

Modifying a D–A–π–A–D HTM system for higher hole mobility by themeta-substitution strategy to weaken the electron-donating ability of the donor unit: a DFT study

Wang

et al. 2023

Nanoscale

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Computational design of p-(dimethylamino)benzylidene-derived push–pull polyenes with high first-hyperpolarizabilities

Abstract: High first-hyperpolarizabilities of p-(dimethylamino)benzylidene-based D–π–A NLO-phores: multiple theoretical investigations on the substituents and the conjugated bridge effect.

Cited by 8 publications

References 60 publications

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

Enhancing Reverse Intersystem Crossing in Triptycene-TADF Emitters: Theoretical Insights into Reorganization Energy and Heavy Atom Effects

Modifying a D–A–π–A–D HTM system for higher hole mobility by themeta-substitution strategy to weaken the electron-donating ability of the donor unit: a DFT study

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