Pure E/Z isomers of N-methylpyrrole-benzohydrazide-based BF2 complexes: remarkable aggregation-, crystallization-induced emission switching properties and application in sensing intracellular pH microenvironment

Yu, Yi‐Zhe; Yu, Changjiang; Wu, Qinghua; Wang, Hua; Jiao, Lijuan; Wong, Wai Yeung; Hao, Erhong

doi:10.1039/c9tc00473d

Cited by 21 publications

(10 citation statements)

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“…The fluorescence quantum yield (Φ) of PHABr was measured in solution at pH = 10.0 by relative methods using quinine sulfate QS as standard (0.546 in H 2 SO 4 1.00 N, excited at 365 nm) according to [24,50,51]. The value Φ = 2.40% is comparable to that reported for similar amphiphilic pH sensing systems [43,52] and also for intracellular pH sensing molecules [53]. The weak solution emission efficiency is typical of AIE (aggregation-induced emission) active molecules [24,54,55], and is due to the free molecular rotation, which activates a nonradiative decay.…”

Section: Resultssupporting

confidence: 56%

An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

et al. 2019

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A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA+) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirornments. The pyridinoyl-hydrazone moiety acts as the pH-sensitive fluorophore/chromophore probe. Extensive physicochemical characterization has been performed on the bromide salt PHABr. DFT calculations, based on single-crystal X-ray data, permitted to rationalize the optical behavior. Molecular dynamics simulations permitted to clarify the mode of interaction with lipid membrane. The ability of the probe to change color and fluorescence in response to different pH and media of different polarity has been investigated. PHABr shows a remarkable pH-dependent behavior in both absorption and fluorescence spectra with high sensitivity and strong on-off switch effect at neutral pH, perceptible even to the naked eye.

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Section: Resultssupporting

confidence: 56%

An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

et al. 2019

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“… 910 Other AIE-based sensors for determination of pHi make use of smartly functionalized anthracenes, 911 of BF 2 chelates 912 , 913 or of E / Z isomers of N -methylpyrrole-benzohydrazide-based BF 2 complexes, these also containing >C=N– bonds of the Schiff base type and undergoing pH-induced AIE. 914 They were applied to the determination of the pHi of living cancer cells. It should be mentioned that most of the pH probes based on AIE are expected to show the same limitations as molecular probes, that is, shift of the calibration due to interaction of the biomolecules with the monomeric form of the dye.…”

Section: Nanomaterialsmentioning

confidence: 99%

“…Some show dual emission and therefore enable ratiometric intracellular sensing . Other AIE-based sensors for determination of pHi make use of smartly functionalized anthracenes, of BF 2 chelates , or of E / Z isomers of N -methylpyrrole-benzohydrazide-based BF 2 complexes, these also containing >CN– bonds of the Schiff base type and undergoing pH-induced AIE . They were applied to the determination of the pHi of living cancer cells.…”

Section: Nanomaterialsmentioning

confidence: 99%

Optical Sensing and Imaging of pH Values: Spectroscopies, Materials, and Applications

2020

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This is the first comprehensive review on methods and materials for use in optical sensing of pH values and on applications of such sensors. The Review starts with an introduction that contains subsections on the definition of the pH value, a brief look back on optical methods for sensing of pH, on the effects of ionic strength on pH values and p K a values, on the selectivity, sensitivity, precision, dynamic ranges, and temperature dependence of such sensors. Commonly used optical sensing schemes are covered in a next main chapter, with subsections on methods based on absorptiometry, reflectometry, luminescence, refractive index, surface plasmon resonance, photonic crystals, turbidity, mechanical displacement, interferometry, and solvatochromism. This is followed by sections on absorptiometric and luminescent molecular probes for use pH in sensors. Further large sections cover polymeric hosts and supports, and methods for immobilization of indicator dyes. Further and more specific sections summarize the state of the art in materials with dual functionality (indicator and host), nanomaterials, sensors based on upconversion and 2-photon absorption, multiparameter sensors, imaging, and sensors for extreme pH values. A chapter on the many sensing formats has subsections on planar, fiber optic, evanescent wave, refractive index, surface plasmon resonance and holography based sensor designs, and on distributed sensing. Another section summarizes selected applications in areas, such as medicine, biology, oceanography, bioprocess monitoring, corrosion studies, on the use of pH sensors as transducers in biosensors and chemical sensors, and their integration into flow-injection analyzers, microfluidic devices, and lab-on-a-chip systems. An extra section is devoted to current challenges, with subsections on challenges of general nature and those of specific nature. A concluding section gives an outlook on potential future trends and perspectives.

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“…Recently, our group reported a series of highly fluorescent, unsymmetrical, and easily accessible BOPPY dyes (Figure ), which exhibit high solid-state fluorescence and large Stokes shifts while retaining high molar absorption coefficients, excellent photostability, and insensitivity to pH . More recently, we have also developed difluoroboronate-anchored acylhydrazones (BOAHYs) as green fluorescent protein chromophore analogues that exhibit bright fluorescence in the solid state and notable aggregation-induced emission (AIE)-active features despite weak fluorescence in solution . In this work, we hypothesized that pyrrole-substituted acylhydrazones, generated in situ from the condensation of 2-formylpyrroles and acylhydrazines, could be anchored by two BF 2 units in the presence of NEt 3 to form a novel BOPHY-like bis(BF 2 ) chromophore (Figure ).…”

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confidence: 97%

A Family of BODIPY-like Highly Fluorescent and Unsymmetrical Bis(BF₂) Pyrrolyl–Acylhydrazone Chromophores: BOAPY

Fang

et al. 2020

Org. Lett.

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A new family of pyrrolyl–acylhydrazones anchored with two BF2 units, named BOAPY, have been developed as BODIPY-like and unsymmetrical bis(BF2) chromophores via a simple one-pot reaction. The easily accessible scaffold enjoys excellent diversity due to the structural versatilities of 2-formylpyrroles and acylhydrazines. BOAPYs exhibit good molar absorption coefficients, large Stokes shifts, and excellent chemical stability. More importantly, most of them display excellent fluorescence quantum yields both in solution and the solid state (up to 0.88 and 0.64, respectively).

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Pure E/Z isomers of N-methylpyrrole-benzohydrazide-based BF₂ complexes: remarkable aggregation-, crystallization-induced emission switching properties and application in sensing intracellular pH microenvironment

Abstract: Two pairs of pure E/Z isomers of novel BF2 acylhydrozone dyes have been synthesized, which exhibited AIE, viscosity, crystallization, and acid–base-induced emission.

Cited by 21 publications

References 85 publications

An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

Optical Sensing and Imaging of pH Values: Spectroscopies, Materials, and Applications

A Family of BODIPY-like Highly Fluorescent and Unsymmetrical Bis(BF₂) Pyrrolyl–Acylhydrazone Chromophores: BOAPY

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Pure E/Z isomers of N-methylpyrrole-benzohydrazide-based BF2 complexes: remarkable aggregation-, crystallization-induced emission switching properties and application in sensing intracellular pH microenvironment

Abstract: Two pairs of pure E/Z isomers of novel BF2 acylhydrozone dyes have been synthesized, which exhibited AIE, viscosity, crystallization, and acid–base-induced emission.

Cited by 21 publications

References 85 publications

An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

Optical Sensing and Imaging of pH Values: Spectroscopies, Materials, and Applications

A Family of BODIPY-like Highly Fluorescent and Unsymmetrical Bis(BF2) Pyrrolyl–Acylhydrazone Chromophores: BOAPY

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Pure E/Z isomers of N-methylpyrrole-benzohydrazide-based BF₂ complexes: remarkable aggregation-, crystallization-induced emission switching properties and application in sensing intracellular pH microenvironment

A Family of BODIPY-like Highly Fluorescent and Unsymmetrical Bis(BF₂) Pyrrolyl–Acylhydrazone Chromophores: BOAPY