Novel thiazoline-phenothiazine based “push-pull” molecules as fluorescent probes for volatile acids detection

Chaudhary, Shweta; Mukherjee, Madhubani; Paul, Tanmoy Kumar; Taraphder, Srabani; Milton, Marilyn Daisy

doi:10.1016/j.jphotochem.2020.112509

Cited by 16 publications

(9 citation statements)

References 61 publications

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“…The effect of protonation on the absorption and emission properties of tBuTPAterpy was studied in titration experiments conducted with the use of trifluoroacetic acid ( TFA ) in CHCl 3 using the procedure previously described in [ 34 ]. The portions of TFA were selected in order to cover a broad range of titration steps from 1:1 to 1:1000.…”

Section: Resultsmentioning

confidence: 99%

“…In the literature, the band at 330 nm was ascribed to 1 π → 1 π* transitions of the protonated terpy unit [ 76 , 77 ]. Instead, the spectral red shift in the visible region was attributed to the enhancement of the tBuTPAterpy ICT character due to the electron-withdrawing increase of the terpy acceptor upon protonation [ 34 ]. Isosbestic points at 352 nm and 398–434 nm indicate the presence of multiple protonated–neutral forms in equilibrium between each other.…”

Section: Resultsmentioning

confidence: 99%

“…Most importantly, the introduction of strong electron donating groups into the electron acceptor terpy core gives rise to Intraligand Charge Transfer (ICT) transitions, which offer a large degree of control over the system’s optical properties [ 27 , 28 ]. Other remarkable aspects of these compounds are their optical sensitivity to the pH, polarity and viscosity of the local environment [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ].…”

Section: Introductionmentioning

confidence: 99%

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Push-Pull Effect of Terpyridine Substituted by Triphenylamine Motive—Impact of Viscosity, Polarity and Protonation on Molecular Optical Properties

Maroń

Cannelli²,

Socie³

et al. 2022

Molecules

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The introduction of an electron-donating triphenylamine motive into a 2,2′,6′,2′′-terpyridine (terpy) moiety, a cornerstone molecular unit in coordination chemistry, opens new ways for a rational design of photophysical properties of organic and inorganic compounds. A push-pull compound, 4′-(4-(di(4-tert-butylphenyl)amine)phenyl)-2,2′,6′,2′′-terpyridine (tBuTPAterpy), was thoroughly investigated with the use of steady-state and time-resolved spectroscopies and Density Functional Theory (DFT) calculations. Our results demonstrate that solvent parameters have an enormous influence on the optical properties of this molecule, acting as knobs for external control of its photophysics. The Intramolecular Charge Transfer (ICT) process introduces a remarkable solvent polarity effect on the emission spectra without affecting the lowest absorption band, as confirmed by DFT simulations, including solvation effects. The calculations ascribe the lowest absorption transitions to two singlet ICT excited states, S1 and S2, with S1 having several orders of magnitude higher oscillator strength than the “dark” S2 state. Temperature and viscosity investigations suggest the existence of two emitting excited states with different structural conformations. The phosphorescence emission band observed at 77 K is assigned to a localized 3terpy state. Finally, protonation studies show that tBuTPAterpy undergoes a reversible process, making it a promising probe of the pH level in the context of acidity determination.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Push-Pull Effect of Terpyridine Substituted by Triphenylamine Motive—Impact of Viscosity, Polarity and Protonation on Molecular Optical Properties

Maroń

Cannelli²,

Socie³

et al. 2022

Molecules

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“…3(b), (d) and (f)). 50–52 These outcomes indicate that protonation of pyridine's nitrogen atom enhances the ICT character of the D molecule. When compared to the other acids used, sample D could sense HCl much more efficiently than TFA as well as AA owing to the strong acidic nature of HCl, and as a result, HCl can bind more strongly with compound D than TFA and AA.…”

Section: Resultsmentioning

confidence: 99%

Protonation induced redshift in the fluorescence of a pyridine derivative as a potential anti-counterfeiting agent

Devadiga

Ahipa

2022

Soft Matter

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“…[18] They are characterized by their simple synthesis and structural modification, intense luminescence, and high yield. [19,20] Phenothiazines have a nonplanar butterfly shape that prevents the formation of intermolecular excimers and aggregations. The two external phenyl rings were shown to be arranged with a small torsion angle compared with sulphur and nitrogen heteroatoms.…”

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confidence: 99%

Development of a push–π–pull phenothiazine‐vinyl‐isophorone fluorophore: a novel solvatochromic and pH indicator

Alahmdi

2023

Luminescence

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Knoevenagel condensation of phenothiazine‐3,7‐dicarbaldehyde with an isophorone yielded a new phenothiazine derivative (PTZ‐c) fluorophore. The solvatochromic and pH‐sensing abilities of PTZ‐c, an asymmetric fluorophore with a single isophorone molecule, were shown to be exceptional. PTZ‐c produced very delicate absorbance and emission spectra. When the polarity of the solvent was increased, the PTZ‐c emission spectra showed greater sensitivity than the absorption spectra. Multiple spectroscopic techniques, including Fourier transform infrared spectroscopy, nuclear magnetic resonance, and mass spectrometry, were used to characterize the manufactured PTZ‐c sensor. To demonstrate the beneficial solvatochromic behaviour associated with intramolecular charge transfer, the absorption spectra of the synthesized DA PTZ‐c dye were analyzed in different solvents of varying polarity. Band intensity and the wavelength of PTZ‐c emission were also found to be highly solvent dependent. It was observed that when solvent polarity was increased to a maximum of 4122 cm−1, Stokes’ shift also increased. To analyze the Stokes' shift that depended on the solvent, a linear correlation between solvation and energy was used. An investigation of PTZ‐c quantum yield (ф) was also conducted. Both the absorbance and fluorescence spectra of the sensor in dimethylformamide as a function of pH were studied. A fluorescence peak was seen at 562 nm, whereas the greatest absorption wavelengths were found at 403 and 317 nm. It was shown that the pH‐sensing mechanism depended on protons removed from the PTZ‐c chromophore, which caused a colour shift and variation in both emission and colorimetric properties.

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Novel thiazoline-phenothiazine based “push-pull” molecules as fluorescent probes for volatile acids detection

Cited by 16 publications

References 61 publications

Push-Pull Effect of Terpyridine Substituted by Triphenylamine Motive—Impact of Viscosity, Polarity and Protonation on Molecular Optical Properties

Push-Pull Effect of Terpyridine Substituted by Triphenylamine Motive—Impact of Viscosity, Polarity and Protonation on Molecular Optical Properties

Protonation induced redshift in the fluorescence of a pyridine derivative as a potential anti-counterfeiting agent

Development of a push–π–pull phenothiazine‐vinyl‐isophorone fluorophore: a novel solvatochromic and pH indicator

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