Symmetrical and unsymmetrical thiazole-based ESIPT derivatives: the highly selective fluorescence sensing of Cu<sup>2+</sup> and structure-controlled reversible mechanofluorochromism

Gayathri, Parthasarathy; Kanagajothi, Karuppaiah; Nag, Probal; Anand, Neethu; Reddy, V. Sivaranjana; Moon, Dohyun; Anthony, Savarimuthu Philip; Madhu, Vedichi

doi:10.1039/d1ce00927c

Cited by 8 publications

(6 citation statements)

References 88 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…TPA‐AP with all other metal ions including Cr 3+ and Fe 2+ /Fe 3+ does not show any fluorescence. It is unusual because paramagnetic Cu 2+ coordination is expected to quench the fluorescence 39,40 …”

Section: Resultsmentioning

confidence: 99%

Cu²⁺ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position

Ravi,

Priyadharshini,

Al‐Zahrani

et al. 2024

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

Triphenylamine (TPA)‐based Schiff base chemosensors ((E)‐2‐((4‐(diphenylamino)benzylidene)amino)phenol [TPA‐AP], (E)‐5‐(diphenylamino)‐2‐(((2‐hydroxyphenyl)imino)methyl)phenol [HTPA‐AP], and (E)‐5‐(diphenylamino)‐2‐((phenylimino)methyl)phenol [HTPA‐A]) were synthesized and explored the role of metal chelating hydroxyl functionality position for heavy metal ion sensing. TPA‐AP and HTPA‐AP showed Cu2+ ion‐induced chemical transformation and produced oxazole derivatives with turn‐on fluorescence. In contrast, HTPA‐A exhibited metal chelation‐induced turn‐on fluorescence for Zn2+ ion. The reactive chemical sensing of TPA‐AP and HTPA‐AP led to high selectivity of Cu2+, and other ions did not show any interference. The concentration‐dependent studies of Cu2+ and Zn2+ indicated the limit of detection (LOD) up to 6.07 × 10−7 and 4.6 × 10−7 M, respectively. Further, Cr3+, Fe3+, and Fe2+ coordination with TPA‐AP and HTPA‐AP exhibited visible color change from colorless to yellow. However, the yellow color was disappeared and becomes colorless due to imine hydrolysis. Interestingly, all three metal ions showed different rate of hydrolysis and color disappearance. TPA‐AP with Fe3+ exhibited fast hydrolysis and immediate color change whereas Fe2+ and Cr3+ required longer time. But HTPA‐AP and HTPA‐A produced stable complexes with Cr3+, Fe2+, and Sn2+ and Fe3+ alone showed hydrolysis. Thus, the present studies provide structural insight for designing reactive fluorescence and colorimetric Schiff base chemosensor for heavy metal ions.

show abstract

Section: Resultsmentioning

confidence: 99%

Cu²⁺ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position

Ravi,

Priyadharshini,

Al‐Zahrani

et al. 2024

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

show abstract

“…Madhu et al 38 synthesized probes 5 & 6 for Cu 2+ detection in an ACN : water mixture. Probe 5 consists of two symmetrical thiazole rings fused together to provide p-p stacking arrangement, whereas 6 is composed of a thiazole ring & Schiff base to give an unsymmetrical molecule with face-to-edge arrangements, which facilitate intramolecular H-bonding and ESIPT signal (Fig.…”

Section: Esipt-based Probes For Cationsmentioning

confidence: 99%

ESIPT-based probes for cations, anions and neutral species: recent progress, multidisciplinary applications and future perspectives

Nehra,

Kaushik

2023

Anal. Methods

View full text Add to dashboard Cite

show abstract

“…In terms of ESIPT molecules, very few studies have been performed to analyze the effect of temperature or other extrinsic conditions on the emission properties of thin films. In particular, temperatures above room temperature were reported to induce a change in the FL of the ESIPT emission, but these studies were performed either in solution or the bulk solid state (i.e., powder or crystal). − To the best of our knowledge, the effect of thermal annealing on ESIPT thin films has not been studied, which, together with morphological analysis, is of relevant interest for different applications such as optoelectronic or photovoltaic devices.…”

Section: Introductionmentioning

confidence: 99%

Balancing the Push–Pull Effect on the Synthesis and Fluorescent Properties of New ESIPT Dyes for Thin Film Applications

Arenhart Soares,

Martinez-Denegri,

Baptista

et al. 2023

J. Phys. Chem. C

View full text Add to dashboard Cite

The development of functional materials exploiting excited-state intramolecular proton transfer (ESIPT) requires a deep understanding of the push−pull balance on their reactivity, emission mechanism, and response to the surrounding environment. In this study, we focused on the model 2-(2-hydroxyphenyl)benzothiazole (HBT) core, and we have developed a simplified synthetic pathway to obtain two new ESIPT dyes with amide groups at the para or meta positions of the phenolic ring. We studied the impact of the geometry of the push−pull system for the two HBT isomers, unraveling that it strongly influenced their reactivity patterns and fluorescence emission. The ESIPT emission of the new molecules in the solution was affected by the solvent polarity, transitioning from pure keto to pure enol emission as the solvent polarity was increased. In the spin-coated films, the intermolecular interactions generated by the push−pull balance and the molecular shape of the deposited materials were also found to be essential for defining their morphology and the related emissive properties. Furthermore, these features were tuned by applying thermal annealing or by changing the solvent used for thin film deposition. The combination of both strategies was employed to provide a more favorable molecular ordering and to increase the fluorescence quantum yield of the neat films by 150%.

show abstract

Symmetrical and unsymmetrical thiazole-based ESIPT derivatives: the highly selective fluorescence sensing of Cu²⁺ and structure-controlled reversible mechanofluorochromism

Abstract: Excited state intramolecular proton transfer (ESIPT) process based organic fluorophores provided opportunity to develop large Stokes shifted multifunctional fluorescence systems for white light emitting, chemosensing and bioimaging applications. In this...

Cited by 8 publications

References 88 publications

Cu²⁺ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position

Cu²⁺ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position

ESIPT-based probes for cations, anions and neutral species: recent progress, multidisciplinary applications and future perspectives

Balancing the Push–Pull Effect on the Synthesis and Fluorescent Properties of New ESIPT Dyes for Thin Film Applications

Contact Info

Product

Resources

About

Symmetrical and unsymmetrical thiazole-based ESIPT derivatives: the highly selective fluorescence sensing of Cu2+ and structure-controlled reversible mechanofluorochromism

Abstract: Excited state intramolecular proton transfer (ESIPT) process based organic fluorophores provided opportunity to develop large Stokes shifted multifunctional fluorescence systems for white light emitting, chemosensing and bioimaging applications. In this...

Cited by 8 publications

References 88 publications

Cu2+ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position

Cu2+ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position

ESIPT-based probes for cations, anions and neutral species: recent progress, multidisciplinary applications and future perspectives

Balancing the Push–Pull Effect on the Synthesis and Fluorescent Properties of New ESIPT Dyes for Thin Film Applications

Contact Info

Product

Resources

About

Symmetrical and unsymmetrical thiazole-based ESIPT derivatives: the highly selective fluorescence sensing of Cu²⁺ and structure-controlled reversible mechanofluorochromism

Cu²⁺ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position

Cu²⁺ catalyzed benzoxazole formation from Schiff base: Reactive organic chemosensors and effect of hydroxyl position