Amino derivatives of 1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline – Photophysics and implementation of molecular logic switches

Uchacz, Tomasz; Szlachcic, Paweł; Wojtasik, Katarzyna; Mac, Marek; Stadnicka, Katarzyna

doi:10.1016/j.dyepig.2015.09.016

Cited by 20 publications

(8 citation statements)

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“…16 In recent years, the synthesis and fluorescent properties of a series of 6-aminoquinolines were reported. [17][18][19][20][21][22] As an example, this kind of molecule has shown luminescent properties, with potential applications in organic solar cells (OSCs), biomolecular markers, organic light-emitting diodes (OLEDs), molecular probes and switches. 17,19 Application of 6-aminoquinolines in photoluminescent sensors to detect different metals in solution has also been highlighted.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical, thermal and antimycobacterial properties of novel 6-amino-2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl) quinolines

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical, thermal and antimycobacterial properties of novel 6-amino-2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl) quinolines

et al. 2019

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“…Studying the bond lengths between the substituents and the pyrazoloquinoline core it is crucial to note that the shortest length is observed for N–C at the first position 1.422 Å, then for C–C at the third position 1.484 Å, and finally 1.524 Å for C–C at the fourth position. The first two values do not deviate much from those reported for 6-ethyl-1,3-diphenyl-pyrazoloquinoline [ 37 ], showing electronic coupling occurring between phenyl rings and the core. In the case of the substituent at the fourth position, a clear single molecular bond is observed pointing to a lack of electronic conjugation between the receptor and the chromophore.…”

Section: Resultsmentioning

confidence: 53%

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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“…Molecules 2022, 27, x FOR PEER REVIEW 41 of 67 sensor for many bivalent cations and that, more importantly, its selectivity can be easily enhanced by the addition of small amounts of water to the fluorescing medium. Three years later, Uchacz et al investigated a series of donor-acceptor 1H-pyrazolo [3,4-b]quinolines that were substituted with different amine donors (i.e., N,N-dimethylamine, N,N-diphenylamine, N,N-phenyl-1-naphthylamine and carbazole groups), with the aim of implementing them as pH-sensitive molecular logic switches [178]. The authors showed that, in the presence of trifluoroacetic acid (the input signal), the fluorescence of the investigated pyrazoloquinolines was almost completely quenched, which was due to the formation of a nonemissive protonated adduct.…”

Section: Application Of Pyrazoloquinolines In Fluorescence Sensingmentioning

confidence: 99%

1H-Pyrazolo[3,4-b]quinolines: Synthesis and Properties over 100 Years of Research

et al. 2022

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This paper summarises a little over 100 years of research on the synthesis and the photophysical and biological properties of 1H-pyrazolo[3,4-b]quinolines that was published in the years 1911–2021. The main methods of synthesis are described, which include Friedländer condensation, synthesis from anthranilic acid derivatives, multicomponent synthesis and others. The use of this class of compounds as potential fluorescent sensors and biologically active compounds is shown. This review intends to summarize the abovementioned aspects of 1H-pyrazolo[3,4-b]quinoline chemistry. Some of the results that are presented in this publication come from the laboratories of the authors of this review.

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Amino derivatives of 1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline – Photophysics and implementation of molecular logic switches

Cited by 20 publications

References 57 publications

Synthesis and photophysical, thermal and antimycobacterial properties of novel 6-amino-2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl) quinolines

Synthesis and photophysical, thermal and antimycobacterial properties of novel 6-amino-2-alkyl(aryl/heteroaryl)-4-(trifluoromethyl) quinolines

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

1H-Pyrazolo[3,4-b]quinolines: Synthesis and Properties over 100 Years of Research

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