A simple acidic ‘turn-on’ fluorescent pH probe based on BOPYIN and its visual detection and cellular imaging

Yuan, Xiaofeng; Zhang, Tingting; Yan, Jiaying; Chen, Xi; Wang, Long; Liu, Xiang; Zheng, Kaibo; Zhang, Nuonuo

doi:10.1016/j.dyepig.2020.108318

Cited by 24 publications

(14 citation statements)

References 49 publications

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“…Nine seven-membered BOPYINs were synthesized with 26-50 % isolated overall yields by Knoevenagel condensation on πenlarged or unmodified indole units (1) and substituted or unmodified pyrrole units (2), then coordination with BF 3 • OEt 2 via a facile, two-step, one-flask synthetic procedure (Scheme 1). All compounds are characterized by 1 H-NMR, 13 C-NMR and high resolution mass spectrum (HRMS) analysis (Figure S6-S32), which are well consistent with their structure information.…”

Section: Synthesis and Characterizationsupporting

confidence: 65%

“…1 H NMR (400 MHz, DMSO-d 6 ) δ 8.34 (d, J = 12.2 Hz, 1H), 8.06 (d, J = 7.9 Hz, 1H), 7.71 (d, J = 7.0 Hz, 1H), 7.55-7.40 (m, 3H), 6.88 (t, J = 7.4 Hz, 2H), 4.28 (q, J = 7.1 Hz, 2H), 1.51 (s, 6H), 1.31 (t, J = 7.1 Hz, 3H). 13 C NMR (101 MHz, DMSO-d 6 ) δ 183. 09, 163.67, 144.00, 143.12, 136.63, 133.73, 128.89, 128.09, 127.76, 123.09, 121.19, 118.47, 115.20, 108.49, 59.93, 52.48, 23.63, 14.24…”

Section: Methods Bmentioning

confidence: 99%

“…1 H NMR (400 MHz, DMSO-d 6 ) δ 8.04 (d, J = 8.0 Hz, 1H), 7.88 (s, 1H), 7.70 (d, J = 3.4 Hz, 1H), 7.67 (s, 1H), 7.49 (t, J = 7.2 Hz, 1H), 7.43 (t, J = 7.3 Hz, 1H), 7.36 (s, 1H), 6.63 (d, J = 11.9 Hz, 1H), 4.23 (q, J = 7.1 Hz, 2H), 1.50 (s, 6H), 1.28 (t, J = 7.1 Hz, 3H). 13 C NMR (101 MHz, DMSO-d 6 ) δ 183. 57, 183.55, 163.04, 144.19, 142.71, 139.40, 139.30, 133.87, 132.75, 128.79, 127.41, 122.96, 122.44, 119.51, 118.30, 105.95, 59.63, 52.54, 23.83, 14.26…”

Section: Bo-4ementioning

confidence: 99%

“…[12] Subsequently, 6-amino BOPYIN as a fluorescent probe showed high selective and sensitive to acid, which successfully applied for visual detection and cellular imaging. [13] BOPYINs contain a central seven-membered core ring with NÀ B-N coordination, which is similar to BODIPYs. As we all know, BODIPYs intrinsically contain highly planar core leading to π-π packing, weak or non-emission in solid state and small Stokes shift.…”

Section: Introductionmentioning

confidence: 99%

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A Study of the Functionalisation of BOPYIN Dyes: Synthesis and Photophysical Properties**

et al. 2022

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Borondifluoride‐3,3‐dimethyl‐2‐[2‐(2‐pyrrolyl) ethenyl] indole (BOPYIN), a seven‐membered, nonplanar boron complex, features typical photophysical properties, such as relatively large Stokes shift. Herein, a series of BOPYINs are prepared by a two‐step, one‐flask synthesis. Based on the modification position, these derivatives could be divided into three sections, including withdrawing substituted dyes, dyes with donating substitution on the pyrrole unit, and dyes with further π‐enlarged substitution on indole unit. The relationship between diverse modified structures and photophysical properties are systematically discussed by experiments and DFT calculations. This work illustrates that donating‐group modifications on pyrrole and π‐enlargement on the indole unit may promote the red shift of the photophysical spectra synergistically.

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Section: Synthesis and Characterizationsupporting

confidence: 65%

Section: Methods Bmentioning

confidence: 99%

Section: Bo-4ementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Study of the Functionalisation of BOPYIN Dyes: Synthesis and Photophysical Properties**

et al. 2022

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“…Compared with traditional methods, fluorescence technology has become an attractive tool for environmental detection and biological imaging because of its easy visualization and operation, low cost, excellent selectivity, and sensitivity. [7][8][9] More importantly, it is particularly useful when it needs to be mainly located in single cell components and environmental water samples, because it can accurately feed back real-time information about cell and environmental water samples. In the past few years, as a focus in the field of sensing analytes, many pH sensors have been developed in the fields of environment, biomedicine and industry, which have the advantages of high chemical selectivity, biocompatibility and high sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Highly Reversible “Off‐On‐Off” Dual‐channel Fluorescence Probe Based on Amino Pyrazole and Phenothiazine for Sensing Extremely Alkaline Solution

Zhao

et al. 2022

ChemistrySelect

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Acid-base balance is related to many cell functions, and its disorders can lead to many diseases. Real-time detection of intracellular pH fluctuation is very important to prevent many diseases and environmental water samples. Here, we report a dual-channel fluorescence probe PTZ-aminopyrazole based on low-cost phenothiazine and 3-aminopyrazole, which can detect pH fluctuation highly sensitively through protonation under acidic condition and deprotonation under alkaline condition.The probe exhibits a fluorescence intensity and UV absorbance characteristics in the extreme acidity range of 2.6-5.5 and especially in the extreme alkaline range of 11.1-13.8, respectively. In addition, PTZ-aminopyrazole has high pH-selective reaction to metal ions, good reversibility and excellent photostability. Furthermore, PTZ-aminopyrazole can be fixed on a test paper, which shows a rapid and reversible colorimetric response to HCl/NaOH vapor with naked-eye.

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Highly Stable Univalent Copper of a Cu@Al/SBA‐15 Nanocomposite Catalyzes the Synthesis of Fluorescent Aminobenzotriazoles Derivatives

Luo

Tian

Pei

et al. 2021

Chemistry A European J

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With the development of green chemistry, it is still a challenge to maintain the unstable valence state of the metal in heterogeneous catalysts and realize new catalytic synthesis methods. In this paper, it is reported that an univalent copper nanocomposite (Cu@Al/SBA‐15) can efficiently catalyze the formation of novel amino‐containing benzotriazoles with great fluorescence properties in a new synthetic strategy. Subsequently, its application is further verified by an acylation reaction to produce a series of novel benzotriazoles derivatives with high yield. It is worth noting that the Cu@Al/SBA‐15 nanocomposites not only enable the reaction completed with high yield in a short time, but can also be recycled many times without a significant reduction in activity, and the leaching of copper and aluminum species in reaction system is negligible. Finally, the detailed and feasible reaction mechanism is also provided.

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A simple acidic ‘turn-on’ fluorescent pH probe based on BOPYIN and its visual detection and cellular imaging

Cited by 24 publications

References 49 publications

A Study of the Functionalisation of BOPYIN Dyes: Synthesis and Photophysical Properties**

A Study of the Functionalisation of BOPYIN Dyes: Synthesis and Photophysical Properties**

Highly Reversible “Off‐On‐Off” Dual‐channel Fluorescence Probe Based on Amino Pyrazole and Phenothiazine for Sensing Extremely Alkaline Solution

Highly Stable Univalent Copper of a Cu@Al/SBA‐15 Nanocomposite Catalyzes the Synthesis of Fluorescent Aminobenzotriazoles Derivatives

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