1H-Pyrazolo[3,4-b]quinoline derivative with the chelating substituent: Synthesis and spectral properties as a fluorescent sensor for cation detection

Danel, Andrzej; Kolbus, A.; Grabka, Danuta; Kucharek, Mateusz; Pokładko-Kowar, Monika

doi:10.1016/j.dyepig.2021.109713

Cited by 5 publications

(5 citation statements)

References 42 publications

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“…Using the formula

, the LOD of Zn 2+ was estimated to be 1.93 × 10 −7 M and is approximately 90 times lower than the ligand concentration. This is a lower LOD value than for the pyrazoloquinoline derivative with crown moiety, which was 5.97 × 10 −6 M [ 41 ], and similar to the LOD of the derivative with a diethylamine substituent, which was equal to 4 × 10 −7 M [ 40 ].…”

Section: Resultsmentioning

confidence: 68%

“…The binding constant for the PQPc complex with Zn 2+ cation was estimated to be 859 M −1 ( Figure 8 b). This value is comparable to the complexes formed by the derivative with a crown moiety (978 M −1 ) [ 41 ], but much lower compared with the complexes formed with divalent ions by the derivative with a diethylamine substituent (the binding constant of the order of magnitude 10 3 –10 10 M −1 ) [ 40 ].…”

Section: Resultsmentioning

confidence: 84%

“…The introduction of a dipicolylamine substituent at the fourth position in the pyridine ring of the parent skeleton gave a pyrazoloquinoline derivative with much better selective properties than the previously studied derivative with a crown moiety at the fourth position. PQPc gives a clear reaction to one specific cation—Zn 2+ , while the derivative with a crown moiety showed weaker selectivity toward the studied ions [ 41 ]. However, in the presence of Co 2+ , Cu 2+ , and Ni 2+ ions, the fluorescence of the Zn 2+ -PQPc complex is quenched.…”

Section: Resultsmentioning

confidence: 99%

“…The resulting bromoderivative 4 was subjected to the reaction with dipicolylamine in the presence of anhydrous potassium carbonate resulting in the final compound, PQPc. The syntheses of 3 and 4 were described in our previous paper [41]. S7 and S8).…”

Section: Synthesismentioning

confidence: 99%

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Fluorescent Sensor Based on 1H-Pyrazolo[3,4-b]quinoline Derivative for Detecting Zn2+ Cations

Kolbus,

Uchacz,

Danel

et al. 2024

Molecules

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The photophysical and sensory properties of the donor–acceptor pyrazoloquinoline derivative (PQPc) were investigated using absorption, steady-state, and time-resolved fluorescence measurements. The compound synthesized from commercial, readily available substrates exhibited absorptions in the UV–Vis range, with a maximum of the longwave band around 390 nm. The maximum fluorescence was around 460–480 nm, depending on the solvent. The quantum yield was between 12.87% (for n-hexane) and 0.75% (for acetonitrile) and decreased with increasing solvent polarity. The PET mechanism was implicated as the cause of fluorescence quenching. Divalent ions such as Zn2+, Pb2+, Cd2+, Ca2+, Mg2+, Co2+, Ni2+, and Cu2+ were introduced to study the fluorescent response of PQPc. A 13-times increase in fluorescence quantum yield was observed after the addition of Zn2+ ions. Detailed research was carried out for the PQPc-Zn2+ system in order to check the possibility of analytical applications of PQPc as a fluorescent sensor. A detection limit of Zn2+ was set at the value level 1.93 × 10−7 M. PQPc-Zn2+ complexes had a stoichiometry of 1:1 with a binding constant of 859 M−1. Biological studies showed that the sensor was localized in cells near the membrane and cytoplasm and may be used to detect zinc ions in eukaryotic cells.

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“…Using the formula

Section: Resultsmentioning

confidence: 68%

Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

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Fluorescent Sensor Based on 1H-Pyrazolo[3,4-b]quinoline Derivative for Detecting Zn2+ Cations

Kolbus,

Uchacz,

Danel

et al. 2024

Molecules

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“…The difference between the two molecules lies in the structure of crown ether: the crown ether ring of CDT-S contains both S and N heteroatoms, while that of CDT-N only contains N heteroatom. According to previous reports, S or N atoms in crown ether could enhance the interaction between crown ether and Pb 2 + , [26,28] which may result in more effective Pb 2 + passivating ability. Results demonstrate that CDT-S could more effectively passivate defects and meanwhile improve the crystal quality of perovskite films.…”

Section: Introductionmentioning

confidence: 79%

Organic Semiconductor Based on N, S‐Containing Crown Ether Enabling Efficient and Stable Perovskite Solar Cells

Chen,

Zeng,

Gao

et al. 2023

ChemSusChem

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The uncoordinated lead cations are ubiquitous in perovskite films and severely affect the efficiency and stability of perovskite solar cells (PSCs). In this work, 15‐crown‐5 with various heteroatoms are connected to the organic semiconductor carbazole diphenylamine, and two new compounds, CDT‐S and CDT‐N, are developed to modify the Pb2+ defects in perovskite films through the anti‐solvent method. Apart from the oxygen atoms, there are also N atoms on crown ether ring in CDT‐N, and both S and N heteroatoms in CDT‐S. The heteroatoms enhance the interaction between the crown ether‐based semiconductors and the undercoordinated Pb2+ defect in perovskite. Particularly, the stronger interaction between S atoms and Pb2+ further enhances the defect passivation effect of CDT‐S than CDT‐N, thereby more effectively suppressing the non‐radiative recombination of charge carriers. Finally, the efficiency of the device treated with CDT‐S is up to 23.05%. Moreover, the unencapsulated device based on CDT‐S maintained 90.5% of the initial efficiency after being stored under dark conditions for 1000 hours, demonstrating good long‐term stability. Our work demon‐strates that crown ethers are promising in perovskite solar cells, and the crown ether containing multiple heteroatoms could effectively improve both efficiency and stability of devices.

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A simple and efficient synthesis of 1,3,6-trisubstituted pyrazoloquinolines via intramolecular cyclization – optimization studies

Kucharek¹,

Danel

Gut

2022

Chem Heterocycl Comp

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1H-Pyrazolo[3,4-b]quinoline derivative with the chelating substituent: Synthesis and spectral properties as a fluorescent sensor for cation detection

Cited by 5 publications

References 42 publications

Fluorescent Sensor Based on 1H-Pyrazolo[3,4-b]quinoline Derivative for Detecting Zn2+ Cations

Fluorescent Sensor Based on 1H-Pyrazolo[3,4-b]quinoline Derivative for Detecting Zn2+ Cations

Organic Semiconductor Based on N, S‐Containing Crown Ether Enabling Efficient and Stable Perovskite Solar Cells

A simple and efficient synthesis of 1,3,6-trisubstituted pyrazoloquinolines via intramolecular cyclization – optimization studies

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