Substituent-modulated aggregation-induced emission and solid-state acid/base sensing applications of pyrazole-based donor-acceptor derivatives

Dwivedi, Bhupendra Kumar; Bhowmik, Pradip K.; Pandey, Daya Shankar

doi:10.1016/j.dyepig.2022.110444

Cited by 6 publications

(2 citation statements)

References 67 publications

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“…are assisted by intermolecular H‐bonding. Therefore, we envisaged that the compounds containing carbonyl oxygen might also be utilized as probes for acidochromism [58–73] …”

Section: Introductionmentioning

confidence: 99%

“…Therefore, we envisaged that the compounds containing carbonyl oxygen might also be utilized as probes for acidochromism. [58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73] In this work, we have designed and synthesized a series of three symmetrical red-colored chalcone derivatives containing two non-planar electron-rich phenothiazine units linked together through a cross-conjugated system, giving a D-π-A-π-D type push-pull molecular arrangement (Figure 1). To fine tune the photophysical properties, different alkyl chains (n = 2À 4) were substituted at position 10 of the phenothiazine units.…”

Section: Introductionmentioning

confidence: 99%

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Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Kumari

Milton

2022

Eur J Org Chem

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We report on a series of phenothiazine‐based D‐π‐A‐π‐D type cross‐conjugated non‐doped red‐emitting molecules synthesized by simple Claisen‐Schmidt condensation, which exhibit excellent AIEE phenomena through the formation of large‐sized nano‐aggregates. These thermally stable red fluorescent organic materials have low band gap energies (Eg=1.84–2.15 eV) and also display reversible mechanofluorochromism. The CIE chromaticity coordinates of red emissive ground powders were closer to the standard red‐light chromaticity coordinates. These chalcones also exhibited positive solvatochromism, and large Stokes shifts. Finally, these compounds were utilized as reversible volatile acid sensors to detect TFA in solution as well as in solid state, by virtue of the presence of electron withdrawing carbonyl oxygen, and they could detect TFA at a concentration as low as 15.8 ppm in the presence of C4.

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“…are assisted by intermolecular H‐bonding. Therefore, we envisaged that the compounds containing carbonyl oxygen might also be utilized as probes for acidochromism [58–73] …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Kumari

Milton

2022

Eur J Org Chem

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Efficient Synthesis of Fully Substituted and Diversely Functionalized Pyrazoles through p‐TSA Catalyzed One‐Pot Condensation of Cyclic β‐Diketones, Arylglyoxals and Arylhydrazones

Dhurey,

Mandal,

Pramanik

2023

Eur J Org Chem

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A one‐pot, three‐component, and atom economic synthesis of biologically and pharmaceutically important fully substituted and functionalized pyrazole derivatives has been accomplished under metal‐catalyst‐free benign conditions. The strategy involves early condensation of readily available cyclic β‐diketones (dimidone, 4‐hydroxycoumarin and 2‐hydroxy‐1,4‐naphthoquinone) and arylglyoxals to generate a chalcone type intermediate which upon acid catalyzed condensation with ambident nucleophile arylhydrazones produces various aryl and cyclic β‐diketone substituted pyrazole derivatives. The synthesis embraces high functional group tolerance, broad substrate scope, excellent yield of the products, short reaction time and operationally simple and mild reaction conditions. The synthesis provides an easy opportunity of incorporating biologically important N‐diarylsulfide/selenide functionality, various enolisable cyclic β‐diketones and other bioactive heterocycles concurrently to pyrazole, which may help in designing and development of pyrazole derivatives of pharmacological significance.

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Metal‐free Synthesis of Trisubstituted Pyrazoles by the Reaction Between Hydrazones and Activated Olefins

Bhaskaran¹,

Sreelekha²,

Babu³

2022

ChemistrySelect

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The reactivity of various activated olefins towards the [3 + 2] annulation with hydrazones (aza-enamines) has been studied. Nitroolefins, methyl vinyl ketone, acrylates and acrylamide were found to react with aldehyde hydrazones of different electronic nature to generate 1,3,5-/1,3,4-trisubstituted pyrazoles selectively. A detailed optimization study was conducted to derive the best condition for the annulation reaction of different olefin partner and the intermediate dihydropyrazole is also identified. Recently, metal-free routes for pyrazoles were reported by Ueda et al [18] and Ma et al. in an effective manner. Very recently Zhu et al (2021) reported the synthesis of 5-trifluorometh-[a]

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Substituent-modulated aggregation-induced emission and solid-state acid/base sensing applications of pyrazole-based donor-acceptor derivatives

Cited by 6 publications

References 67 publications

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Efficient Synthesis of Fully Substituted and Diversely Functionalized Pyrazoles through p‐TSA Catalyzed One‐Pot Condensation of Cyclic β‐Diketones, Arylglyoxals and Arylhydrazones

Metal‐free Synthesis of Trisubstituted Pyrazoles by the Reaction Between Hydrazones and Activated Olefins

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