An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core

Eltyshev, Alexander K.; Suntsova, Polina O.; Karmatskaia, Ksenia D.; Taniya, Olga S.; Слепухин, П. А.; Benassi, Enrico; Belskaya, Nataliya P.

doi:10.1039/c8ob02644k

Cited by 11 publications

(7 citation statements)

References 49 publications

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“…Absolute quantum yield study was performed on Horiba FlouroMax 4 Spectrofluorometer (Kyoto, Japan) with Quanta-φ integrating sphere using FluorEssence 3.5 Software. DTPs 1a-e, 2a-c and 3a-b were prepared according to procedures reported in the literature and their spectral characteristics were identical to the published data [8,21]. were prepared via the demethylation of their methoxycongeners by using BBr 3 solution in dichloromethane with special temperature profile regime (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

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Sensitivity of the phenoxy derivatives of 2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones to acidic and basic stimuli

Eltyshev

Belskaya

2021

Chim.Tech.Acta

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Herein we report the research on the sensitivity of six hydroxy derivatives of dihydrotriazolopyrimidines (HO-DTP) to acids and bases. The UV/Vis and fluorescence spectra of these compounds were investigated with the addition of the acids and bases. Spectral data revealed the strong red shifts for emission and absorption maxima in the presence of KOH and NaOH. Moreover, two DTPs demonstrated strengthening of the emission intensity. The obtained results and data published in our previous paper demonstrated the strong and selective sensory response of DTPs to the acids and bases and elucidated relationships between the structure and sensitivity to the environment. This finding allowed us to manage these properties by introducing the combination of substituents and functionalities into the heterocyclic core. Thus, investigations demonstrated the potential of the application of DTPs as chemo- and fluorosensors for selective detection of acids and bases.

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Section: Methodsmentioning

confidence: 99%

“…Recently we reported the synthesis and photophysical properties of new blue and blue-green fluorophores derived on dihydro-1,2,3-triazolopyrimidine core (DTP) [8]. These fluorophores exhibited multifunctional properties and showed good fluorescence in solutions (with QY up to 88%, Stokes shift (SS) ~151 nm and λ em up to 534 nm).…”

Section: Introductionmentioning

confidence: 99%

Sensitivity of the phenoxy derivatives of 2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones to acidic and basic stimuli

Eltyshev

Belskaya

2021

Chim.Tech.Acta

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“…Among the wide variety of azolopyrimidines, special attention should be paid to the isomorphic analogues of naturally occurring purines, 8-azapurines, with useful biological activity , and high photophysical properties. , The structural features of 8-azapurines allow for their substitution of natural purine bases in numerous enzymatic processes, as well as their application as fluorescent probes in enzymology …”

Section: Introductionmentioning

confidence: 99%

“…It has been shown that this method was successfully used for the synthesis of a 2-aryl-1,2,3-triazole ring II (Scheme a) . Another example is construction of 8-azapurine derivatives IV with significant photophysical properties , (Scheme b).…”

Section: Introductionmentioning

confidence: 99%

“…16−20 Among the wide variety of azolopyrimidines, special attention should be paid to the isomorphic analogues of naturally occurring purines, 8-azapurines, with useful biological activity 21,22 and high photophysical properties. 23,24 The structural features of 8-azapurines allow for their substitution of natural purine bases in numerous enzymatic processes, as well as their application as fluorescent probes in enzymology. 25 Despite the pronounced structural diversity of 8-azapurines, polycondensed systems on their basis are presented rather poorly in the literature and their relevance remains to be conclusively demonstrated (Figure 1).…”

Section: ■ Introductionmentioning

confidence: 99%

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Benzimidazoazapurines: Design, Synthesis, and Photophysical Study

et al. 2021

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A highly efficient approach to a new class of polycyclic 8-azapurines, benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidines (BITPs), with good photophysical characteristics is proposed. The approach comprises condensation of aminobenzimidazoles with 3-oxo-2-phenylazopropionitrile to form 3-(arylazo)benzo[4,5]imidazo[1,2-a]pyrimidine-4-amines, which undergo oxidative cyclization by the catalytic action of copper(II) acetate, resulting in BITPs with 73–84% yield. Spectral investigations demonstrated the fluorescent properties of BITPs, exhibiting good quantum yields (up to 60%) with maxima absorption at 379–399 and emission at 471–505 nm.

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2‐Aryl‐2,4‐dihydro‐5H‐[1,2,3]triazolo[4,5‐d]pyrimidin‐5‐ones as a New Platform for the Design and Synthesis of Biosensors and Chemosensors

et al. 2020

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2‐Aryl‐2,4‐dihydro‐5H‐[1,2,3]triazolo[4,5‐d]pyrimidin‐5‐ones (DTPs), which may be considered as analogues of 8‐azapurines, were synthesised. Their structural aspects in the ground and excited states, electronic distributions, and non‐covalent intramolecular interactions were studied using time‐dependent density functional theory. Photophysical investigations demonstrated the variability of the absorption and emission parameters of the DTPs depending on their structure, microenvironment, and external stimuli. The aggregation‐induced emission enhancement effect was confirmed by studying the emission of DTPs in the solid state and by spectral titrations in H2O‐dimethyl sulfoxide (DMSO) and EtOH‐DMSO mixtures. Further investigation revealed the selective sensitivity of DTPs to acids, which strongly depended on their structure. Reversible interactions were found between the DTPs and HCl and subsequently triethylamine, both as vapour stimuli and in solution. Cell imaging experiments showed the potential of the DTPs in fluorescence microscopy bioimaging applications. These findings show that DTPs can be used to fabricate bio‐ and chemosensors.

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An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core

Abstract: A new efficient route for the synthesis of blue fluorescent triazolopyrimidines for biological applications is reported.

Cited by 11 publications

References 49 publications

Sensitivity of the phenoxy derivatives of 2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones to acidic and basic stimuli

Sensitivity of the phenoxy derivatives of 2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones to acidic and basic stimuli

Benzimidazoazapurines: Design, Synthesis, and Photophysical Study

2‐Aryl‐2,4‐dihydro‐5H‐[1,2,3]triazolo[4,5‐d]pyrimidin‐5‐ones as a New Platform for the Design and Synthesis of Biosensors and Chemosensors

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