Synthesis, characterization and investigation of fluorescent Sn2+ probe potential of pyrene-derived monomer and its oligo(azomethine) compound

Yeldir, Elif Karacan; Kaya, İsmet

doi:10.1016/j.eurpolymj.2022.111229

Cited by 7 publications

(2 citation statements)

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“…Poly(azomethine)s have emerged as prominent subjects of investigation owing to their intricate optical and electronic characteristics and have been extensively reviewed in the context of optoelectronic appliances with the inclusion of polymer light-emitting diodes and polymer solar cells. − The isoelectronic character of the azomethine (imine, –HCN) bonds present in oligo(azomethine)s or poly(azomethine)s has engendered similar optoelectronic performance attributes across their corresponding polymers, , exemplified by poly( p -phenylenevinylene), a material amenable to fine-tuning its properties to manifest a notable fluorescence quantum yield upon doping, alongside robust chemical and electrochemical resistance. − Poly(azomethine)s offer a host of advantages, as they can be synthesized via metal-free polycondensation with water as the sole byproduct. − …”

Section: Introductionmentioning

confidence: 99%

Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Kolcu,

Çulhaoğlu,

Kaya

2024

ACS Omega

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Oligo(azomethine)s bearing phosphate and silane moieties were the subject of an investigation within this study. The initial stage involved the synthesis of two Schiff base monomers, denoted as SCH-1 and SCH-2 (SCHs), each possessing a pair of hydroxyl functional groups. This was achieved through a loss of water between the aldehyde and diamine precursors. Subsequently, the Schiff base entities were subjected to oligomerization through HCl-mediated elimination due to the interaction between the hydroxyl groups of the Schiff bases and the chlorine moieties of dichlorodiethylsilane (Si) or phenyl dichlorophosphate (P). This procedure yielded distinct P-oligo(azomethine) (P1−P, P2−P) and Si-oligo(azomethine) (P1−Si and P2−Si) structures corresponding to each precursor. The molecular structures of the synthesized Schiff base monomers and oligo(azomethine)s were elucidated employing Fourier transform infrared, 1 H NMR, and 13 C NMR techniques. Thermal properties of the resulting products were assessed by utilizing thermogravimetric analysis (TG-DTG/ DTA and DSC) techniques. Scanning electron microscopy (SEM) was employed to acquire high-resolution images and detailed surface information on the samples. Additionally, X-ray diffraction was employed to analyze the phase properties of the solid samples. Furthermore, the optical band gap (E g ) values of the resulting P-oligo(azomethine)s and Si-oligo(azomethine)s were determined utilizing UV−vis spectrophotometer. The relatively low band gap values exhibited by the synthesized oligo(azomethine)s were indicative of their potential suitability as semiconductive materials in the realm of electronic and optoelectronic device fabrication. Photoluminescence (PL) measurements disclosed a green emission profile upon excitation by blue light. The oligo(azomethine)s incorporating methoxy groups demonstrated a red shift in comparison to their counterparts with methyl groups. Remarkably, no discernible fluctuations in fluorescence were observed over a 3600 s interval under consistent conditions. This observation underscored the inherent stability of the PL emission across the spectral range of exciting light. Thermal analyses unveiled high thermal stability of the synthesized oligo(azomethine)s, sustaining their structural integrity up to 220 °C. The char % of P-oligo(azomethine)s and Si-oligo(azomethine)s were observed to fall within the range of 29.45−55.47% at 1000 °C. SEM images revealed the absence of pores on the surface of P2−Si, which exhibited the highest limiting oxygen index and thermal heat release index (T HRI ) values.

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Section: Introductionmentioning

confidence: 99%

Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Kolcu,

Çulhaoğlu,

Kaya

2024

ACS Omega

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“…Recently, a monomeric Schiff base was synthesized via a reaction between o-vanillin and 1-aminopyrene. Interestingly, it exhibited a distinctive sensitivity to Sn 2+ in comparison with various other metal ions [11]. However, the cytotoxic activities of pyrene-based Schiff base complexes are scarce or lacking.…”

Section: Introductionmentioning

confidence: 99%

Novel Schiff Base Derived from Amino Pyrene: Synthesis, Characterization, Crystal Structure Determination, and Anticancer Applications of the Ligand and Its Metal Complexes

Aazam,

Majrashi

2023

Molecules

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In this study, we report the cytotoxicity of a newly synthesized Schiff base HL ((E)-2-ethoxy-6((pyren-1-ylimino)methyl)phenol) and its derived metal complexes (Zn(II), Cu(II), Co(II), Cr(III), and Fe(III)) along with their structural characterizations by means of elemental analysis, magnetic moment, molar conductance, IR, UV-Vis, ESR, and mass spectrometry. The single X-ray diffraction of the HL shows that it exists in the phenol-imine form in its solid state. The NMR and IR data indicate that the bidentate binding of the Schiff base ligand with the metal center occurs during complexation through the azomethine nitrogen atom and the hydroxyl group oxygen atom of the 3-ethoxy salicylaldehyde. The electronic spectra and magnetic measurements indicate that the Co(II) complex has a tetrahedral geometry and that the Cr(III) and Fe(III) complexes have a distorted octahedral geometry. The ESR and electronic spectra suggest that the Cu(II) complex has a distorted tetrahedral geometry. The cytotoxic effects of the HL and all of the metal complexes were studied using human breast cancer (MCF-7) cells. The Cu(II) and Zn(II) complexes exhibited the highest activity against the tested cell line, with IC50 values of 5.66 and 12.74 μg/mL, respectively, and their activity was higher than that of the fluorouracil cancer drug against the MCF-7 cells (18.05 μg/mL).

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Tetraphenylsilane-based oligo(azomethine)s containing 3,4-ethylenedioxythiophene units along their backbone: Optical, electronic, thermal properties and computational simulations

Sobarzo

González

Jessop

et al. 2022

European Polymer Journal

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Synthesis, characterization and investigation of fluorescent Sn2+ probe potential of pyrene-derived monomer and its oligo(azomethine) compound

Cited by 7 publications

References 53 publications

Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Comparative Study of Bis-Schiff Case Containing Conjugated Oligomers Based on Phosphate and Silane Moieties: Investigation of Photophysical and Thermal Properties

Novel Schiff Base Derived from Amino Pyrene: Synthesis, Characterization, Crystal Structure Determination, and Anticancer Applications of the Ligand and Its Metal Complexes

Tetraphenylsilane-based oligo(azomethine)s containing 3,4-ethylenedioxythiophene units along their backbone: Optical, electronic, thermal properties and computational simulations

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