Chemical and photophysical studies on the interaction of reactive oxygen species with carbonylated diazo derivatives: Their chromogenic, fluorescent detection and mechanistic investigation

Patel, Samridhi; Patra, Sisir Kumar; Chand, Samiksha; Singh, R. V.; Singh, Indrani; Chandra, Girish

doi:10.1016/j.dyepig.2023.111317

Cited by 7 publications

(2 citation statements)

References 42 publications

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“…Azobenzene dye 6 , fluorinated azo dye 7 , and azo Schiff bases 1–4 were synthesised following well-established protocols with minor modifications. 45 Thus, aniline and fluoro-aniline diazotized with salicylaldehyde 5 provided compounds 6 and 7 , respectively. Further condensation with aniline and fluoro-aniline in the presence of catalytic acetic acid provided a set of azo Schiff bases 1–4 in a reasonably good yield (35–45% in two steps).…”

Section: Resultsmentioning

confidence: 96%

Studies on the effect of fluorine on the interaction of different metal ions with a fluorinated azobenzene-Schiff base: intramolecular C–F activation under polar solvent

Patel,

Chandra

2024

New J. Chem.

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Section: Resultsmentioning

confidence: 96%

Studies on the effect of fluorine on the interaction of different metal ions with a fluorinated azobenzene-Schiff base: intramolecular C–F activation under polar solvent

Patel,

Chandra

2024

New J. Chem.

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“…The presence of two benzene rings connected by -N=N-bond makes them have a special photophysical property and has been widely used for light-responsive materials. Many probes have been developed as chemical sensors for the detection of varieties of ions and molecules [2,3].…”

Section: Introductionmentioning

confidence: 99%

Azobenzenes: Photoswitching and Their Chemical Sensor Application

Chandra,

Rani,

Mahto

et al. 2024

Dye Chemistry - Exploring Colour From Nature to Lab

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Azobenzene is a well-known dye that undergoes fast trans-cis photoisomerization and has been widely studied and used in the development of organic functional materials. Due to its selective isomeric distribution in the excited state, azobenzene has been used as a photoswitch in the storage of information on a molecular level, photo-controllable catalysis, solar light harvesting, photo-pharmacology, optical-to-mechanical energy conversion, molecular electronic, and photonic devices. Furthermore, the characteristic and distinguishable photoelectronic properties of trans and cis azobenzene have been recently used in the sensing properties of different ions and the recognition of molecules. Here, we are going to review the recent literature where different intermolecular forces show the supramolecular properties under the stimuli of photo-light.

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Light Triggered Reversible Aggregation/Dispersion of Hydroxy Azo‐benzenes During Photo Switching: Solvent, Ions Assisted Dispersion, and Induced Quenching Emission

Patel,

Das,

Mishra

et al. 2024

ChemPhotoChem

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Hydroxy azo‐benzenes are very well known for their rapid trans ⇆ cis photoisomerization under polar solvents. In contrast, we synthesized two hydroxymethylated‐hydroxyazobenzene derivatives and investigated their light‐triggered photoisomerization and stability under polar solvents. The result showed just opposite behavior and very slow trans ⇆ cis isomerization was observed (minutes‐days). Thus, the UV‐vis spectrum revealed a very low decrease in the absorbance of p‐p* transition. Surprisingly, the isomerization process became faster with the addition of ionic species. Here, we attempted to understand the underlying cause of the unusual photo‐switching behavior. The presence of hydroxymethyl and fluorine substituents was found to have a significant effect on the stability of the trans and photo‐isomerized cis products. Here, it was confirmed with NMR and DLS studies that the unusual photostability of trans compounds was caused by polar solvent‐assisted aggregation (hydrodynamic radius, RH 5660‐1720 nm) which underwent dispersion (RH, 220‐68 nm) and formed a significant stable solvated photoproduct under photoirradiation. Furthermore, this aggregation‐dispersion was found to be very slowly reversible. Further, the fluorescence emission demonstrated a characteristic dispersion‐induced quenching. Regular photoswitching was observed under non‐polar conditions in benzene where an expected blue shift of p‐p* transition and an increase in the intensity of n‐p* transitions.

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Chemical and photophysical studies on the interaction of reactive oxygen species with carbonylated diazo derivatives: Their chromogenic, fluorescent detection and mechanistic investigation

Cited by 7 publications

References 42 publications

Studies on the effect of fluorine on the interaction of different metal ions with a fluorinated azobenzene-Schiff base: intramolecular C–F activation under polar solvent

Studies on the effect of fluorine on the interaction of different metal ions with a fluorinated azobenzene-Schiff base: intramolecular C–F activation under polar solvent

Azobenzenes: Photoswitching and Their Chemical Sensor Application

Light Triggered Reversible Aggregation/Dispersion of Hydroxy Azo‐benzenes During Photo Switching: Solvent, Ions Assisted Dispersion, and Induced Quenching Emission

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