Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection

Kuzu, Burak; Ekmekci, Zeynep; Tan, Meltem; Mengeş, Nurettin

doi:10.1007/s10895-021-02716-1

Cited by 13 publications

(8 citation statements)

References 56 publications

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“…The oligoesters′ terminal−OH proton chemical shift value appeared at around 11.77–10.29 ppm. The −OH protons create a partial positive charge, leading to intramolecular hydrogen bonding with azine nitrogen (−N=C−), resulting in a considerable deshielding effect 1 H‐NMR spectrum [27,28] . The EMDMP and EMDOP oligoesters show more aromatic proton shift values at around 8.21–6.78 ppm and aliphatic proton shifts at 2.22 and 1.51 ppm of EMDAP.…”

Section: Resultsmentioning

confidence: 99%

“…The À OH protons create a partial positive charge, leading to intramolecular hydrogen bonding with azine nitrogen (À N=CÀ ), resulting in a considerable deshielding effect 1 H-NMR spectrum. [27,28] The EMDMP and EMDOP oligoesters show more aromatic proton shift values at around 8.21-6.78 ppm and aliphatic proton shifts at 2.22 and 1.51 ppm of EMDAP. The results indicate the incorporation of phenyl groups and adipoyl groups in the main chain of oligoesters.…”

Section: Spectral Characterizationsmentioning

confidence: 99%

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Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe²⁺ ion detection

et al. 2023

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Azine‐based monomer and its three oligoesters were synthesized, characterized with IR, UV, GC‐MS, GPC, 1H NMR, 13C{1H} NMR, 31P NMR and applied to chemosensor applications. In the chemosensor study, fluorophores show selective and sensitive responses with Fe2+ ions in the DMF/H2O solution (1 : 1, pH: 7.4, fluorophore: 5 μM). The quenching of fluorescence intensity with the addition of Fe2+ ion gives the correlation coefficient (R2) value above 0.99286, exhibiting good binding stoichiometry nature of fluorophores with Fe2+ than the oligoesters. The high detecting capability of oligoesters is further ascertained by its higher LOD than the monomer (5.05×10−7). The binding constant values of fluorophores obtained from the Benesi‐Hildebrand plot show that the oligoesters have a higher binding ability (1.0012–1.0025 M−1) with Fe2+ ion than the monomer (1.0011 M−1). The conductivity nature of the oligoester gradually increased with the contact time of iodine. After 96hr of iodine doping, EMDAP exhibits higher conductivity (1.98×10−3 Scm−1) than the other oligoesters due to higher electron‐density nitrogen atoms in the structure. The EMDOP shows high dielectric constant value because of its π‐π interaction, loosely attached π electrons and high dipole moment values. All these experimental results are validated with the theoretical (DFT) approach by optimizing the structure of the fluorophore with B3LYP/6‐311++G(d,p) level basis set. The DFT approach also explains the mechanism of fluorescence quenching and the exact binding sites of fluorophores with Fe2+ ions.

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Section: Resultsmentioning

confidence: 99%

Section: Spectral Characterizationsmentioning

confidence: 99%

Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe²⁺ ion detection

et al. 2023

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“…As a result, we tested various oxidants for the cyclization of pyrrole 4a (Table 2 ) and SeO 2 was found to be the best oxidant for converting the methyl group into aldehyde (entries 4), a process known as the Riley oxidation. 15c , 17` b c d The other oxidants, such as CAN 18a (Table 2 , entry 2) and KMnO 4 18b (entry 3) did not give any cyclic product.…”

Section: Table 1 Optimization Of Reaction Conditions Fo...mentioning

confidence: 97%

A Golden Synthetic Approach to 2-(1H-Pyrrol-1-yl)anilines and Pyrrolo[1,2-a]quinoxalines through a Gold Carbene Intermediate

Menges,

Tasdemir,

Genç

2023

Synlett

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The pyrrolo[1,2-a]quinoxaline skeleton has significant potential for many biological and optical applications. Hence, in this study, unconjugated ynone derivatives are reacted with 1,2-diaminoarenes under gold-catalyzed cyclization. The reaction gives 2(1H-pyrrole-1yl)-aniline, which is a valuable starting material, and Pyrrolo[1,2-a]quinoxaline through a one-pot and single-step approach. A reaction mechanism for the formation of the pyrrolo[1,2-a]quinoxaline skeleton featuring a key gold-carbene intermediate is proposed. On the other hand, the methyl group on the C-2 position of 2(1H-pyrrole-1yl)-anilines is oxidized with SeO2, resulting in a pyrrolo[1,2-a]quinoxaline skeleton, which gives 14 different pyrrolo[1,2-a]quinoxaline derivatives.

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“…These structures are logically arranged and include significant functional groups that might be relevant in future applications. 14,15 In this study, we investigated imidazole compounds with ESIPT emission for cell imaging. As a result, numerous imidazole derivatives were synthesized, and their ESIPT emission potentials were measured.…”

Section: ■ Introductionmentioning

confidence: 99%

“…On the other hand, in the past few years, our research group found out that the carbonyl functional group at the C-2 position of imidazole 1 and indole derivatives 2 can make ESIPT emission (Figure A). These structures are logically arranged and include significant functional groups that might be relevant in future applications. , …”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of ESIPT-Based Imidazole Derivatives for Cell Imaging

Gül,

Açıkgöz,

Çakır

et al. 2024

ACS Omega

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Excited-state intramolecular proton transfer (ESIPT)-based fluorescent molecules offer several exciting applications and are utilized most frequently as a cell imaging agent. Because of this, four distinct imidazole derivatives with ESIPT emission have been synthesized, and their fluorescence characteristics have been assessed in a variety of settings. Measurements using fluorescence spectroscopy have shown a promising candidate for cell staining, and potential candidate was specifically investigated for cell imaging uses in HT-29, MDA-MB-231, and HaCaT. Cytotoxicity of candidate molecule (1d) was analyzed using HT-29 and HaCaT cell lines, and at a dosage of 160 μM, HT-29 and HaCaT cell lines showed no signs of important cell toxicity. When spectroscopically measured, compound 1d showed no fluorescence ability in phosphate-buffered saline (PBS) solution. However, after 8 h of incubation in several cell lines, excellent fluorescence characteristics were seen in the green and red filters.

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Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection

Cited by 13 publications

References 56 publications

Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe²⁺ ion detection

Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe²⁺ ion detection

A Golden Synthetic Approach to 2-(1H-Pyrrol-1-yl)anilines and Pyrrolo[1,2-a]quinoxalines through a Gold Carbene Intermediate

Design and Synthesis of ESIPT-Based Imidazole Derivatives for Cell Imaging

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Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection

Cited by 13 publications

References 56 publications

Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe2+ ion detection

Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe2+ ion detection

A Golden Synthetic Approach to 2-(1H-Pyrrol-1-yl)anilines and Pyrrolo[1,2-a]quinoxalines through a Gold Carbene Intermediate

Design and Synthesis of ESIPT-Based Imidazole Derivatives for Cell Imaging

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Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe²⁺ ion detection

Synthesis and structural characterization of azine based oligoesteric chemosensors for Fe²⁺ ion detection