Some spirobiindane based 1H-pyrazolo [3,4-b] quinoline chromophore as novel chromophore for light-emitting diodes

Gondek, E.; Danel, A.; Nizioł, Jacek; Armatys, P.; Kityk, I.V.; Szlachcic, Paweł; Karelus, Marcin; Uchacz, Tomasz; Chwast, Jacek; Lakshminarayana, G.

doi:10.1016/j.jlumin.2010.05.033

Cited by 26 publications

(5 citation statements)

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“…However, the rigidity of the pyrazoloquinoline skeleton promotes electronically allowed emission, as the frontier orbitals that participate in the 1 CT→S0 transition have parallel orientation and are, therefore, markedly overlapped [161]. Subsequently, 1H-pyrazolo [3,4-b]quinolines are highly fluorescent in the blue or greenish-blue parts of the spectrum, with quantum fluorescence yields reaching unity in some cases (Figure 15) [20,158,162]. Generally, the absorption spectra of 1H-pyrazolo [3,4-b]quinolines contain two absorption bands in the UV-Vis region of light: I) The broad S 0 →S 1 (π→π*) transition with an absorption maxima that ranges from ca.…”

Section: Structure-property Relationshipmentioning

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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Section: Structure-property Relationshipmentioning

confidence: 99%

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

et al. 2022

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“…The method is highly useful for aniline and its 4‐substituted derivatives (R 6 as substituent). The yields are good to excellent – 40–96% – almost independently of the substituent (for examples see ). On the other hand, for the 3‐subtituted anilines, two isomers are always formed, because the reaction is not regioselective in its origin.…”

Section: Introductionmentioning

confidence: 97%

Facile and Regioselective Synthesis of Substituted 1H‐Pyrazolo[3,4‐b]quinolines from 2‐Fluorobenzaldehydes and 1H‐Pyrazol‐5‐amines

Szlachcic

Kucharek

Jarosz

et al. 2016

Journal of Heterocyclic Chem

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The present article concerns the scope and limitations of the regioselective condensation of 2‐fluorobenzaldehydes with 1H‐pyrazol‐5‐amines, leading to the synthesis of substituted 1H‐pyrazolo[3,4‐b]quinolines (PQ), in the presence of a base catalyst (DABCO and 2,4,6‐trimethylpyridine). A method to obtain these nitrogen heterocycles with fluorine or trifluoromethyl substituents in different positions in the carbocyclic ring was developed as a part of a systematic research on the influence of fluorine‐containing substituents on the parameters of PQ. Those compounds, characterized by high‐fluorescence intensity, have been tested as emitters for the organic light‐emitting diodes since 1997. The functionalization of PQ causes changes in various parameters, for example, HOMO and LUMO levels, which are important for the adjustment of fabricated organic light‐emitting diodes. One of the easiest methods of PQ preparation, namely, the condensation of substituted anilines with 5‐chloro‐1H‐pyrazole‐4‐carbaldehydes, is not regioselective. The method described in this study allows synthesizing of 1H‐pyrazolo[3,4‐b]quinolines with good yields and high selectivity – only the expected isomer is obtained. As various different 2‐fluorobenzaldehydes are commercially available, and 1H‐pyrazol‐5‐amines with different substituents are easy to prepare, the method could be a good alternative to the already known procedures. All possible mechanisms of the reaction were also thoroughly studied.

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“…Pyrazoloquinolines have been shown to be efficient organic emitters, [16][17][18] with applications in fluorescence sensing 19,20 and electroluminescence. 21 Recently, a derivative of this class of compounds showed a selective binding to human telomeric G4 multimers over monomeric ones. 22 The structures, functions, and binding modes for some recently developed c-MYC Pu22 G4 ligands are summarized in Table S1 (ESI †).…”

Section: Introductionmentioning

confidence: 99%

A novel fluorescent probe with a pyrazolo[4,3-c]quinoline core selectively recognizes c-MYC promoter G-quadruplexes

et al. 2022

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Some spirobiindane based 1H-pyrazolo [3,4-b] quinoline chromophore as novel chromophore for light-emitting diodes

Cited by 26 publications

References 28 publications

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

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

Facile and Regioselective Synthesis of Substituted 1H‐Pyrazolo[3,4‐b]quinolines from 2‐Fluorobenzaldehydes and 1H‐Pyrazol‐5‐amines

A novel fluorescent probe with a pyrazolo[4,3-c]quinoline core selectively recognizes c-MYC promoter G-quadruplexes

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