Synthesis and optical properties of the first representatives of N,N-disubstituted aminostyryl D–π–A chromophores with tunable hydroxytricyanopyrrole (HTCP) acceptor

Федосеев, С. В.; Belikov, М. Yu.; Ievlev, Mikhail Yu.

doi:10.1016/j.dyepig.2022.110455

Cited by 6 publications

(6 citation statements)

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“…Previously it was shown, that the formation of HTCP based D‐ π ‐A chromophores was possible via condensation with aldehydes [11b,e,14] . The reaction proceeds from fair to very good yields (52–77 %) in the presence of an equimolar amount of ammonium acetate in acetonitrile at 20 °C using amino‐substituted benzaldehydes [11f] …”

Section: Resultsmentioning

confidence: 99%

“…To study the dependence of the optical properties of chromophores on the structure of the HTCP acceptor, we modified it with respect to the OH group. For this purpose, 2‐(3‐cyano‐5‐alkoxy‐4,5‐dimethyl‐1,5‐dihydro‐2 H ‐pyrrol‐2‐ylidene)malononitriles RO‐TCP 2 a – e were obtained in 78–89 % yield by the interaction of the initial HTCP acceptor with alcohols in an acidic medium according to the previously developed by us method [11b–f] . The intermediate compounds 2 were further condensed with 2‐morpholinobenzaldehyde in acetonitrile in the presence of an equimolar amount of ammonium acetate at 20 °C to give previously unknown 2‐(5‐alkoxy‐3‐cyano‐5‐methyl‐4‐(2‐morpholinostyryl)‐1,5‐dihydro‐2 H ‐pyrrol‐2‐ylidene)malononitriles 3 a – e in 68–77 % yield (Scheme 2, Table 2).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Tunable Fluorescence of N,N‐Disubstitute ortho‐Aminostyryl D‐π‐A Chromophores Based on a Hydroxytricyanopyrrole (HTCP) Acceptor

Федосеев

Belikov

2023

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The first representatives of a new group of fluorescent donor‐acceptor chromophores, the key structural fragments of which are an easily modifiable hydroxytricyanopyrrole (HTCP) acceptor and an N,N‐disubstituted ortho‐aminostyryl donor fragment, were synthesized. By changing the substituent on both the donor and acceptor fragments, the possibility of varying the emission maxima in the solid state in the red region in the range of 620–732 nm was achieved. It was shown that the introduction of an alkoxy group into the pyrrole ring of HTCP leads to an increase in the quantum yield (Φc) of solid state emission to 9.5 %. In the liquid phase HTCP‐chromophores fluoresce in the range of 621–639 nm with a relative quantum yield of up to 5.5 % The energy values found for the band gap of HTCP chromophore with ortho‐morpholinostyryl donor fragment were in the range of 2.38–2.41 eV.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis and Tunable Fluorescence of N,N‐Disubstitute ortho‐Aminostyryl D‐π‐A Chromophores Based on a Hydroxytricyanopyrrole (HTCP) Acceptor

Федосеев

Belikov

2023

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“…N , N -dimethylthiocarbamate served as a response site for the sensitive and specific detection of HOCl. HTCP was synthesized from 2,3-butanedione and 2-aminoprop-1-ene-1,1,3-tricarbonitrile (92% yield) [ 55 , 56 , 57 ]. Furthermore, N , N -dimethylthiocarbamate was modified to the phenolic hydroxyl position of 4-hydroxybenzaldehyde to obtain NTC (80% yield).…”

Section: Resultsmentioning

confidence: 99%

“…HTCP was prepared following previous literature [ 55 , 56 , 57 ] with slight modifications. We added 2,3-butanedione (2.64 g, 20 mmol) and 2-aminoprop-1-ene-1,1,3-tricarbonitrile (1.72 g, 20 mmol) to a round bottom flask followed by water (40 mL).…”

Section: Methodsmentioning

confidence: 99%

A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid

et al. 2022

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Hypochlorous acid (HOCl) is a reactive substance that reacts with most biomolecules and is essential in physiological and pathological processes. Abnormally elevated HOCl levels may cause inflammation and other disease responses. To further understand its key role in inflammation, HOCl must be detected in situ. Here, we designed a hydroxytricyanopyrrole-based small-molecule fluorescent probe (HTCP-NTC) to monitor and identify trace amounts of HOCl in biological systems. In the presence of HOCl, HTCP-NTC released hydroxyl groups that emit strong fluorescence covering a wide wavelength range from the visible to near-infrared region owing to the resumption of the intramolecular charge transfer process. Additionally, HTCP-NTC demonstrated a 202-fold fluorescence enhancement accompanied by a large Stokes shift and a low detection limit (21.7 nM). Furthermore, HTCP-NTC provided a rapid response to HOCl within 18 s, allowing real-time monitoring of intracellular HOCl. HTCP-NTC exhibited rapid kinetics and biocompatibility, allowing effective monitoring of the exogenous and endogenous HOCl fluctuations in living cells. Finally, based on fluorescence imaging, HTCP-NTC is a potential method for understanding the relationship between inflammation and HOCl.

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“…The research in this direction is relevant due to the possibility of using such structures in various fields, for example, as components of luminescent (colorimetric) sensors and probes, [1][2][3][4][5] nonlinear optical materials, [6][7][8] solar cells [9,10] and solid-state fluorescent dyes. [11][12][13] There are numerous well-studied tricyanofuran (TCF) derivatives [14] among compounds with a BDTC moiety but substituted tricyanopyrroles (TCP) [15][16] and hydroxytricyanopyrroles (HTCP) [17][18][19] are much less common (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

High‐Contrast Optical Nitrile‐Rich Molecular Switches: Synthesis of Pyrrol‐2‐ones Containing a Butadienetricarbonitrile Fragment and Kinetics of Their Reversible Interaction with Morpholine

2023

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Direct synthesis of previously undescribed 5‐aryl‐substituted pyrrol‐2‐one derivatives containing a butadienetricarbonitrile (BDTC) acceptor was carried out. The kinetics of their reversible interaction with morpholine accompanied with high‐contrast color changes in acetonitrile solution was studied for the first time. It was found that the electronic effects of substituents in aromatic ring had a direct effect on the reaction rate and extent, that was supported by the observed linearity between the estimated equilibrium constants and the electrophilic Hammett constants.

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Synthesis and optical properties of the first representatives of N,N-disubstituted aminostyryl D–π–A chromophores with tunable hydroxytricyanopyrrole (HTCP) acceptor

Cited by 6 publications

References 50 publications

Synthesis and Tunable Fluorescence of N,N‐Disubstitute ortho‐Aminostyryl D‐π‐A Chromophores Based on a Hydroxytricyanopyrrole (HTCP) Acceptor

Synthesis and Tunable Fluorescence of N,N‐Disubstitute ortho‐Aminostyryl D‐π‐A Chromophores Based on a Hydroxytricyanopyrrole (HTCP) Acceptor

A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid

High‐Contrast Optical Nitrile‐Rich Molecular Switches: Synthesis of Pyrrol‐2‐ones Containing a Butadienetricarbonitrile Fragment and Kinetics of Their Reversible Interaction with Morpholine

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