Fluorescence detection of Al3+ ion in aqueous medium and live cell imaging by ESIPT probe (E)-N'-(5-bromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide

Bhakta, Viki; Shireen, Zofa; Dey, Sanjit; Guchhait, Nikhil

doi:10.1016/j.saa.2023.122749

Cited by 9 publications

(8 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This was further confirmed by comparing the lifetime values in different solvents at different wavelengths (Table and Figures S19–S21). In the case of nonpolar solvents like CHCl 3 , as we move toward the ESIPT band at 555 nm, initially the contribution of the faster lifetime component increases from 430 to 510 nm and reaches a maximum at 510 nm, and is around 93%. Then, on moving from 540 to 600 nm the contribution of the slower lifetime component increases and that of the faster component decreases.…”

Section: Resultsmentioning

confidence: 94%

“…When the compound was excited at 315 nm, a triexponential decay pattern was observed (Figure A and Table ). The slower lifetime component (∼7.0 ns) was assigned to the lifetime of the local emission of the imine form and the two other components were assigned to the two amine forms. ,,, The contribution of the two amine forms increases as we move toward the low energy ESIPT emission bands. When the assigned anionic emission band was monitored, a faster lifetime component of 0.49 ns was obtained. − Thus, the faster lifetime value of BIBTB in DMSO, ACN, and MeOH solutions was assigned to the anion.…”

Section: Resultsmentioning

confidence: 99%

“…The slower lifetime component (∼7.0 ns) was assigned to the lifetime of the local emission of the imine form and the two other components were assigned to the two amine forms. ,,, The contribution of the two amine forms increases as we move toward the low energy ESIPT emission bands. When the assigned anionic emission band was monitored, a faster lifetime component of 0.49 ns was obtained. − Thus, the faster lifetime value of BIBTB in DMSO, ACN, and MeOH solutions was assigned to the anion. Among the two amine forms, one is formed due to ESIPT toward the imidazole moiety and the other due to ESIPT toward the thiazole moiety.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Dual-Channel Imine-Amine Photoisomerization in a Benzoimidazole and Benzothiazole Coupled System: Photophysics and Applications

Bhakta,

Pramanik,

Guchhait

2024

J. Phys. Chem. A

Self Cite

View full text Add to dashboard Cite

A molecule, namely 2-(1H-benzo [d]imidazol-2-yl)-6-(benzo[d]thiazol-2-yl)-4-bromophenol (BIBTB), having a two-way proton transfer unit of thiazole and imidazole moieties was synthesized and characterized by NMR, electrospray ionization mass spectrometry (ESI-MS), and single-crystal diffraction studies. Steady state and time-resolved spectral studies of BIBTB support excited state intramolecular proton transfer (ESIPT), causing imineamine tautomerization through a two-way 6-membered H-bonded ring, where the N atoms of benzothiazole and the benzoimidazole unit are involved as proton acceptor sites. Interestingly, in a nonpolar and moderately polar solvent, photoisomerization in BIBTB is found to be favored toward the thiazole ring, whereas in a highly polar solvent, it is favored toward the imidazole ring. A spectral comparison of BIBTB with judicially designed molecules 2-(benzo[d]thiazol-2-yl)-4-bromophenol (HBT) and 2-(1H-benzo[d]imidazol-2-yl)-4-bromophenol (BIB) supports these inferences. Theoretical calculation using the Density Functional Theory (DFT) at CAM-B3LYP/6-311+G(d,p) level supports the existence of two low-energy 6-membered hydrogen-bonded planar conformers in the ground state in the gas phase and in solvents of different dielectrics. The potential energy curves (PECs) calculated along the proton transfer (PT) coordinate are found to have a high energy barrier in the ground state and to be barrierless or have a low energy barrier in the excited state for both the forms. The calculated vertical excitation and the emission energy from the relaxed excited and PT states show good correlation with the experimental spectral data. Aggregation of BIBTB in water with red shifted emission was established from X-ray single-crystal structure analysis, solid state emission, and Dynamic Light Scattering (DLS) measurement. The molecule BIBTB also acts as a fluorescence probe for sensing the explosive picric acid in the subnano scale and can be used to determine the proportion of water in dimethyl sulfoxide (DMSO) solvent.

show abstract

Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Dual-Channel Imine-Amine Photoisomerization in a Benzoimidazole and Benzothiazole Coupled System: Photophysics and Applications

Bhakta,

Pramanik,

Guchhait

2024

J. Phys. Chem. A

Self Cite

View full text Add to dashboard Cite

show abstract

“…Intramolecular proton transfer (IPT) is an ultrafast reaction of importance in several types of organic and biological molecules mainly because of its practical applications. − In general, the IPT mechanism appears to be simple, although it cannot always be easily observed spectroscopically . However, IPT may occur in excited states (ES) leading to the so-called ESIPT process.…”

Section: Introductionmentioning

confidence: 99%

Influence of Solvents and Halogenation on ESIPT of Benzimidazole Derivatives for Designing Turn-on Fluorescence Probes

Queiroz,

Alves,

Rivelino

et al. 2024

ACS Omega

View full text Add to dashboard Cite

This work reports a theoretical investigation of the solvent polarity as well as the halogenation of benzimidazole derivatives during excited state intramolecular proton transfer (ESIPT). It details how the environment and halogen substitution may contribute to the efficiency of ESIPT upon keto−enol tautomerism and exploits this effect to design fluorescence sensing. For this purpose, we first examine the conformational equilibrium of benzimidazole derivatives containing different halogen atoms, which results in intramolecular proton transfer, using density-functional theory (DFT) combined with the polarizable continuum model (PCM). Then we evaluate the fluorescence of the benzimidazole derivatives in different dielectric constants within timedependent DFT (TD-DFT) approaches. Our results quantitatively allow the determination of large Stokes shifts in nonpolar solvents around 100 nm. These theoretical results are in agreement with experimental solvatochromism studies of benzimidazoles. The effect of halogenation, with fluorine, chlorine, and bromine, is less important than solvent polarization when ESIPT takes place. Thus, halogenation can be properly chosen depending on the interest of the synthesis of benzimidazole-based turn-on fluorescence in appropriate solvents.

show abstract

“…Excited state intramolecular proton transfer (ESIPT) is a process in which photoexcited molecules relax their energy through tautomerization by the transfer of protons. Since its first report by Weller in methyl salicylate, the phenomenon of ESIPT has stood the test of time and is being used widely by the scientific community to construct sensors, − cell imaging agents, , Laser dyes, and organic light-emitting diode (OLED) materials , to name a few. The large Stokes shift typical of the ESIPT process, the very interesting yet complicated excited-state dynamics, and the ease of coupling competing photophysical phenomena make ESIPT active probes an ideal platform to gain insights into the excited state photoevents by the aid of steady state and time-resolved spectroscopy. − To date, numerous reports regarding the tuning and meticulous studies of ESIPT have been prevalent, reflecting the importance of understanding the exited state photodynamics of such systems. − …”

Section: Introductionmentioning

confidence: 99%

Investigating the Photophysical Aspects of a Naphthalene-Based Excited-State Proton Transfer Dye 1-(1H-Benzo[d]imidazol-2-yl)naphthalen-2-ol: pH-Dependent Modulation of Photodynamics

Bhattacharyya,

Das,

Guchhait

2024

J. Phys. Chem. A

Self Cite

View full text Add to dashboard Cite

The steady state and time-resolved photophysical behavior of a proton transfer dye 1- (1H-benzo[d]imidazol-2yl)naphthalen-2-ol (H-BINO) was investigated. The excited state intramolecular proton transfer (ESIPT) reaction in H-BINO is predominant in nonpolar solutions (toluene and DCM) with a lifetime of ∼1.0 ns. However, in polar media (DMF and MeOH), the excited state photodynamics is characterized by a complex equilibrium of emission from the locally excited state (0.1−2.3 ns), the phototautomer (0.5−1.2 ns), and the anionic emission (2.1−5.4 ns). In the solid state, emission from the various aggregated states dictates the photobehavior. Interestingly, the photodynamics in aqueous solution changes starkly as a function of pH with the anionic (2.1 ns) and phototautomeric (0.5−1.0 ns) emissions guiding the photodynamics as the pH of the medium increases. Optimized structural parameters at the proton donor and acceptor sites for the enol and keto forms and the calculated potential energy curve along the proton transfer coordinate at the density functional theory (DFT) level with the B3LYP/6-311G++(d,p) theory support a favorable and barrierless ESIPT process. The current results will surely boost the ongoing research on small molecule emissive materials.

show abstract

Fluorescence detection of Al3+ ion in aqueous medium and live cell imaging by ESIPT probe (E)-N'-(5-bromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide

Cited by 9 publications

References 37 publications

Dual-Channel Imine-Amine Photoisomerization in a Benzoimidazole and Benzothiazole Coupled System: Photophysics and Applications

Dual-Channel Imine-Amine Photoisomerization in a Benzoimidazole and Benzothiazole Coupled System: Photophysics and Applications

Influence of Solvents and Halogenation on ESIPT of Benzimidazole Derivatives for Designing Turn-on Fluorescence Probes

Investigating the Photophysical Aspects of a Naphthalene-Based Excited-State Proton Transfer Dye 1-(1H-Benzo[d]imidazol-2-yl)naphthalen-2-ol: pH-Dependent Modulation of Photodynamics

Contact Info

Product

Resources

About