A novel colorimetric and fluorescence turn-on pH sensor with a notably large Stokes shift for its application

Ning, Yaoyao; Wang, Xiaoqing; Sheng, Kangjia; Yang, Lili; Han, Wei; Xiao, Chaoni; Li, Jianli; Zhang, Yongmin; Wu, Shaoping

doi:10.1039/c8nj02860e

Cited by 15 publications

(7 citation statements)

References 40 publications

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“…A lot of reported pH probes have some drawbacks such as poor chemo- and photostability, scarce reversibility, and narrow Stokes shifts [49]. Probe PHABr Stokes shifts calculated in the basic range are 102 and 151 nm, respectively, for the aqueous and the ethanolic solution.…”

Section: Resultsmentioning

confidence: 99%

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: Resultsmentioning

confidence: 99%

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

et al. 2019

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“…This sensor gives-off a fluorescence signal change between normal and cancer cells, as function of pH in vitro cytotoxicity [ 22 ]. A similar colorimetric and fluorescence turn-on pH sensor is comprised of a highly colorimetric naphthalenone scaffold ( Figure 1 , box 1) and studied by S. Wu and coworkers [ 40 ]. This sensor shows a color change from light purple to yellow (acid to basic), and a fluorescence signal in the pH range of 9.0–14.0, with an emission from colorless to orange, and finally to yellow (box 1) [ 40 ].…”

Section: Synthetic Visual Ph Sensorsmentioning

confidence: 99%

“…A similar colorimetric and fluorescence turn-on pH sensor is comprised of a highly colorimetric naphthalenone scaffold ( Figure 1 , box 1) and studied by S. Wu and coworkers [ 40 ]. This sensor shows a color change from light purple to yellow (acid to basic), and a fluorescence signal in the pH range of 9.0–14.0, with an emission from colorless to orange, and finally to yellow (box 1) [ 40 ]. This response is associated to an ICT mechanism induced by structural changes caused by -OH group binding, which translate a non-fluorescent molecule into a highly emissive form.…”

Section: Synthetic Visual Ph Sensorsmentioning

confidence: 99%

“…This response is associated to an ICT mechanism induced by structural changes caused by -OH group binding, which translate a non-fluorescent molecule into a highly emissive form. Fluorescence imaging of HeLa cell line reveals a good cell membrane permeability, and its ability for selective monitoring even of extreme basic pH variation [ 40 ].…”

Section: Synthetic Visual Ph Sensorsmentioning

confidence: 99%

“…In these molecules colorimetric effect is the result of ESIPT mechanism. Owing their amphiphilic nature, the charged sensors could potentially interact with cell membrane without altering the bilayer organization [ 40 ]. These sensors show naked-eye on-off switch at neutral pH, absorption and fluorescence response, high sensitivity.…”

Section: Synthetic Visual Ph Sensorsmentioning

confidence: 99%

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Visual pH Sensors: From a Chemical Perspective to New Bioengineered Materials

Costanzo

Panunzi

2021

Molecules

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Many human activities and cellular functions depend upon precise pH values, and pH monitoring is considered a fundamental task. Colorimetric and fluorescence sensors for pH measurements are chemical and biochemical tools able to sense protons and produce a visible signal. These pH sensors are gaining widespread attention as non-destructive tools, visible to the human eye, that are capable of a real-time and in-situ response. Optical “visual” sensors are expanding researchers’ interests in many chemical contexts and are routinely used for biological, environmental, and medical applications. In this review we provide an overview of trending colorimetric, fluorescent, or dual-mode responsive visual pH sensors. These sensors include molecular synthetic organic sensors, metal organic frameworks (MOF), engineered sensing nanomaterials, and bioengineered sensors. We review different typological chemical entities of visual pH sensors, three-dimensional structures, and signaling mechanisms for pH sensing and applications; developed in the past five years. The progression of this review from simple organic molecules to biological macromolecules seeks to benefit beginners and scientists embarking on a project of pH sensing development, who needs background information and a quick update on advances in the field. Lessons learned from these tools will aid pH determination projects and provide new ways of thinking for cell bioimaging or other cutting-edge in vivo applications.

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Chiral amide-bonded hydroxyquinoline-substituted porphyrin fluorescent probes “off–on–off” pH sensing properties

Haider

Gu²,

Tang³

et al. 2022

J Incl Phenom Macrocycl Chem

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A novel colorimetric and fluorescence turn-on pH sensor with a notably large Stokes shift for its application

Abstract: A novel naked-eye colorimetric and fluorescent turn-on pH sensor based on a naphthalenone scaffold was rationally designed and facilely synthesized.

Cited by 15 publications

References 40 publications

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

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

Visual pH Sensors: From a Chemical Perspective to New Bioengineered Materials

Chiral amide-bonded hydroxyquinoline-substituted porphyrin fluorescent probes “off–on–off” pH sensing properties

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