Synthesis, photophysical, viscosity and DFT study of solid state fluorescent molecular rotors

Bhalekar, Sulochana; Avhad, Kiran C.; Sekar, Nagaiyan

doi:10.1016/j.jphotochem.2018.11.027

Cited by 8 publications

(4 citation statements)

References 47 publications

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“…The magnitudes calculated for μ, α 0 , Δ α , β 0 and γ for the molecules by DFT computational method using CAM−B3LYP and BHandHLYP functional and the basis set, 6–31+g(d,p) are summarized in Table and Table S10 . These compounds show higher values of μ, α 0, β 0 and γ compared to those without hydroxy, monocoumarin compound 6c .…”

Section: Resultsmentioning

confidence: 99%

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

2019

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Three novel hydroxyl substituted and triphenylamine sidearm coumarin decorated molecules were prepared to examine the effect of adjacent hydroxyl substituent as well as coumarin units on the photophysical linear and nonlinear optical properties. Both hydroxyl function adjacent to the phenyl ring and extra coumarin unit is attributed to the red shifted absorption (435‐487 nm) and emission (496‐578 nm) compared to the plain triphenylamine based coumarin derivatives. Positive solvatochromism around 70 nm was observed in solvents with different polarity polarities and it is reinforced by solvent polarity plots and multilinear regression study. Very high viscosity induced emission enhancement (5.7 – 8.2 fold) was observed for in ethanol/polyethylene glycol‐400 system, highlighting their capability to act as efficient fluorescent molecular rotors (FMRs). The nonlinear optical properties were investigated by solvatochromism as well as a computational method using B3LYP 6–311++G (d, p) basis set. All these compounds exhibited large magnitudes of first order (65‐208x10 −30e.s.u) and second order (560‐2120x10 −36e.s.u) hyperpolarizability.

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Section: Resultsmentioning

confidence: 99%

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

2019

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“…A solute’s solvatochromic properties have been used in SHG measurements to examine interfacial solvent polarity as a function of solvent structure and substrate composition. , DMABN has a measured ground-state dipole moment of 6.2 D and a TICT-state dipole of 16.5 D . While the resonance-enhanced SHG intensity depends on DMABN’s hyperpolarizability and not its linear absorption cross section, for aromatic solutes having a combination of “push–pull” ligands, these two propertieshyperpolarizability and excited-state dipolehave been shown to track each other. − Despite the solvatochromic evidence for a polar interface, we do not observe the expected corresponding behavior in the SHG intensities for the S 1 and S 2 resonances.…”

Section: Discussionmentioning

confidence: 99%

Buried Liquid Interfaces as a Form of Chemistry in Confinement: The Case of 4-Dimethylaminobenzonitrile at the Silica–Aqueous Interface

et al. 2020

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Time-resolved fluorescence emission and resonance-enhanced second harmonic generation (SHG) spectra were collected from 4-dimethylaminobenzonitrile (DMABN) adsorbed to the aqueous–silica interface in order to identify how strongly associating solvent–substrate interactions change DMABN’s photoisomerization properties. In bulk polar solution, DMABN forms an excited twisted intramolecular charge-transfer (TICT) state that emits with a distinctive, solvatochromic fluorescent signature. At the silica–aqueous interface, the TICT fluorescence disappears, similar to DMABN’s behavior in nonpolar environments. SHG spectra confirm that the interface is, in fact, polar, and DMABN’s unusual fluorescence emission acquired from the interface is attributed to strong hydrogen bonding associations between the water molecules and the silica surface that prevent adsorbate isomerization. Additionally, SHG spectra show a strong resonance at long wavelengths that is unexpected based on bulk absorbance spectra and selection rules for nonlinear hyperpolarizabilities. Using both Zerner’s INDO semiempirical and TD-DFT calculations, this spectroscopic behavior is attributed to a combination of strong electric fields present at the aqueous–silica interface and surface-induced changes to DMABN’s ground-state molecular structure.

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“…The aromatic amine dyes TPA-CN-CHO, PTZ-CNCHO and CZ-CNCHO in this study were synthesized according to previous studies. 36,37…”

Section: Methodsmentioning

confidence: 99%

Facile solvothermal assisted g-C₃N₄post-grafting with aromatic amine dyes for effective photocatalytic hydrogen evolution

et al. 2022

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Synthesis, photophysical, viscosity and DFT study of solid state fluorescent molecular rotors

Cited by 8 publications

References 47 publications

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

Buried Liquid Interfaces as a Form of Chemistry in Confinement: The Case of 4-Dimethylaminobenzonitrile at the Silica–Aqueous Interface

Facile solvothermal assisted g-C₃N₄post-grafting with aromatic amine dyes for effective photocatalytic hydrogen evolution

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Synthesis, photophysical, viscosity and DFT study of solid state fluorescent molecular rotors

Cited by 8 publications

References 47 publications

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

Buried Liquid Interfaces as a Form of Chemistry in Confinement: The Case of 4-Dimethylaminobenzonitrile at the Silica–Aqueous Interface

Facile solvothermal assisted g-C3N4post-grafting with aromatic amine dyes for effective photocatalytic hydrogen evolution

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Facile solvothermal assisted g-C₃N₄post-grafting with aromatic amine dyes for effective photocatalytic hydrogen evolution