Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes

De Meyer, Thierry; Hemelsoet, Karen; Van Speybroeck, Veronique; De Clerck, Karen

doi:10.1016/j.dyepig.2013.10.048

Cited by 109Analytical Chemistry and SensorsMolecular Sensors and Ion DetectionPhotochemistry and Electron Transfer Studies

Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes

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De Meyer, Thierry, Hemelsoet, Karen, Van Speybroeck, Veronique, De Clerck, Karen·2014·Dyes and Pigments

DOI 10.1016/j.dyepig.2013.10.048

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PSP is ring-closed under acidic conditions, while under neutral and alkaline conditions, it loses protons and opens the ring.
“In particular, PSP is ring-closed under acidic conditions, while under neutral and alkaline conditions, it will lose protons and open the ring [35].”
From Red-light excited efficient metal-free near-infrared room-temperature phosphorescent films (2022) · cites this paper as [35]
Section 4.1.1 (page unavailable) supports deprotonation and bond rearrangement, and the Scheme 1 caption says a further deprotonation occurs above pH 6. But it describes the oxygen–carbon bond breaking upon solvation, not ring opening specifically at neutral or alkaline pH; it also does not establish that the dye remains ring-closed throughout acidic conditions. (LLM, conf=0.85)
Experimental — accuracy not yet measured
PSP derivatives are highly sensitive pH indicators in water and have different molecular structures in acidic and neutral aqueous solutions.
“Previous studies revealed that these PSP derivatives are highly sensitive pH indicators in water [35] and have different molecular structures in acidic and neutral aqueous solutions.”
From Red-light excited efficient metal-free near-infrared room-temperature phosphorescent films (2022) · cites this paper as [35]

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High Sensitivity and Reproducibility of a Bismuth/Poly(bromocresol purple) Film Modified Glassy Carbon Electrode for Determination of Trace Amount of Cadmium by Differential Pulse Anodic Stripping Voltammetry
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Poly(ethylene oxide)–silica hybrids entrapping sensitive dyes for biomedical optical pH sensors: Molecular dynamics and optical response
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Sorted by citations

A review on colorimetric indicators for monitoring product freshness in intelligent food packaging: Indicator dyes, preparation methods, and applications
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Recent Progress in Nanomaterial Enabled Chemical Sensors for Wearable Environmental Monitoring Applications
Mamun, M. A. A., & Yuce, M. R. (2020) · Advanced Functional Materials · doi:10.1002/adfm.202005703 · Cited by 202 · see citing works
Colorimetric Nanofibers as Optical Sensors
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Molecular simulation-based insights into dye pollutant adsorption: A perspective review
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Red-light excited efficient metal-free near-infrared room-temperature phosphorescent films
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“Previous studies revealed that these PSP derivatives are highly sensitive pH indicators in water [35] and have differentmolecular structures in acidic and neutral aqueous solutions.”
BackgroundInfluential
Colorimetric Gas Sensing Washable Threads for Smart Textiles
Owyeung, R. E., Panzer, M. J., & Sonkusale, S. (2019) · Scientific Reports · doi:10.1038/s41598-019-42054-8 · Cited by 93 · see citing works
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Recent advances in pH-sensitive indicator films based on natural colorants for smart monitoring of food freshness: a review
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“…indications usually consist of reactive dyes or natural pigments that respond to different colors through physicochemical stimuli such as pH, temperature, humidity, gas, etc., resulting in different changes in the spectrum (De Meyer et al. 2014; Ghaani et al. 2016; Schaefer and Cheung 2018).”
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Preparation of pH‐indicator films based on soy protein isolate/bromothymol blue and methyl red for monitoring fresh‐cut apple freshness
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“This difference is not a matter of ignoring the solvation effect during the structural optimization, since the almost same peak shift from 461 nm to 548 nm has been reported by the TD-DFT calculations for the BTB structures optimized in aqueous solution (performed in Gaussian 03[15] using the B3LYP functional with a 6…”
BackgroundMethodInfluential
Halochromic properties of sulfonphthaleine dyes in a textile environment: The influence of substituents
Meyer, T. D., Steyaert, I., Hemelsoet, K., Hoogenboom, R., Speybroeck, V. V., & Clerck, K. D. (2015) · Dyes and Pigments · doi:10.1016/j.dyepig.2015.09.007 · Cited by 63 · see citing works
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“75) fro orang to gre n as induce by deprotona ion or the rel ase of a proton fr the int llig nt packagin indicat r dye [47].”
BackgroundMethodInfluential
Applications of natural polysaccharide-based pH-sensitive films in food packaging: Current research and future trends
Li, N., Zhou, S., Yang, X., & Lin, D. (2022) · Innovative Food Science & Emerging Technologies · doi:10.1016/j.ifset.2022.103200 · Cited by 48 · see citing works
Plasma dye coating as straightforward and widely applicable procedure for dye immobilization on polymeric materials
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“t defined ranges of pH. For instance, bromothymol blue (BTB) exhibits a yellow colour when dissolved at a pH lower than 6.0, whilst it triggers either green or blue coloration in alkaline environment [50]. Incorporation of a halochromic dye into a desired fibrous matrix could therefore be exploited aiming to integrate…”
BackgroundInfluential
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“The BTB pH indicator is blue above pH = 7.6 and yellow below pH = 6.5, and green between these pH-values (De Meyer et al., 2014).”
BackgroundInfluential
Development of CO2-sensitive antimicrobial bilayer films based on gellan gum and sodium alginate/sodium carboxymethyl cellulose and its application in strawberries
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Removal of wood dyes from aqueous solutions by sorption on untreated pine (Pinus radiata) sawdust
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Flexible pH sensors based on OECTs with a BTB dye-embedded ion-gel gate dielectric
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Acidity Constant (pKa) Calculation of Large Solvated Dye Molecules: Evaluation of Two Advanced Molecular Dynamics Methods
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The colorful world of sulfonephthaleins: Current applications in analytical chemistry for “old but gold” molecules
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Visual investigation of CO2 dissolution and convection in heterogeneous porous media at reservoir temperature and pressure conditions
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A nontoxic reversible thermochromic binary system via π–π stacking of sulfonephthaleins
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Determination of pH Dependent Structures of Thymol Blue Revealed by Cooperative Analytical Method of Quantum Chemistry and Multivariate Analysis of Electronic Absorption Spectra
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Two-layer Electrospun System Enabling Wound Exudate Management and Visual Infection Response
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Halochromic Chemosensor From Poly(acrylonitrile)/Phenolphthalein Nanofibers as pH Sensor
Sharifabad, A. N., & Bahrami, S. H. (2015) · IEEE Sensors Journal · doi:10.1109/jsen.2015.2495338 · Cited by 18 · see citing works
“these dyes is based on ring opening mechanism [2].”
Background
Synthesis of new luminescent bis-azo-linkage Schiff bases containing amino-phenol and its derivative. Part I: Studying of their tautomeric, acidochromic, thermochromic, ionochromic, and photolüminesence properties
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Microfluidic paper-based analytical device for the speciation of inorganic nitrogen species
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Influence of surfactants in improving degradation of polluting dyes photocatalyzed by TiO2 in aqueous dispersion
Germani, R., Bini, M., Fantacci, S., Simonetti, F., TIECCO, M., Vaioli, E., & Giacco, T. D. (2021) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/j.jphotochem.2021.113342 · Cited by 16 · see citing works
Ionochromism, solvatochromism and effect of dissolved gases on the spectral properties of bromothymol blue
Tatini, D., Anselmi, E., Cabrucci, G., Acar, M., Ninham, B. W., & Nostro, P. L. (2022) · Journal of Molecular Liquids · doi:10.1016/j.molliq.2022.120196 · Cited by 15 · see citing works
Generic biomass estimation methods targeting physiologic process control in induced bacterial cultures
Reichelt, W. N., Thurrold, P., Brillmann, M., Kager, J., Fricke, J., & Herwig, C. (2016) · Engineering in Life Sciences · doi:10.1002/elsc.201500182 · Cited by 18 · see citing works
“NH4OH concentration was determined by titration with 1 M HCl, equivalent point was derived by using bromothymol blue as indicator [40].”
Method
Biohythane Production in Hydrogen-Oriented Dark Fermentation of Aerobic Granular Sludge (AGS) Pretreated with Solidified Carbon Dioxide (SCO2)
Kazimierowicz, J., Dębowski, M., & Zieliński, M. (2023) · International Journal of Molecular Sciences · doi:10.3390/ijms24054442 · Cited by 14 · see citing works
Carboxyethylation of chitosan-based polymeric dyes for potential pH-sensing applications
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Simultaneous multi-analyte sensing using a 2D quad-beam diffraction smartphone imaging spectrometer
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Nanofibre-Based Sensors for Visual and Optical Monitoring
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Technological, Ecological, and Energy-Economic Aspects of Using Solidified Carbon Dioxide for Aerobic Granular Sludge Pre-Treatment Prior to Anaerobic Digestion
Kazimierowicz, J., Dębowski, M., & Zieliński, M. (2023) · International Journal of Environmental Research and Public Health · doi:10.3390/ijerph20054234 · Cited by 12 · see citing works
Current applications of colourimetric microfluidic devices (smart phone based) for soil nutrient determination
Cheng, Y., Yang, R. M. H., Maya, F., Li, F., Balavandy, S. K., Wang, L., Breadmore, M. C., Doyle, R. J., & Naidu, R. (2021) · Elsevier eBooks · doi:10.1016/b978-0-12-823696-3.00010-6 · Cited by 12 · see citing works
Radiation-induced coloration of xylenol blue/film containing hexachloroethane for food irradiation applications
Soliman, Y. S., Beshir, W. B., Abdel-Fattah, A. A., Fahim, R. A., & El-Anadouli, B. E. H. (2016) · Journal of Radioanalytical and Nuclear Chemistry · doi:10.1007/s10967-016-4747-z · Cited by 11 · see citing works
“An absorption band at kmax 555 nm, characteristic of protonated quinoid oxygen of XB red form in acidic medium [23, 24, 27], develops upon irradiating XB–PVB film.”
Background
Eco‐Friendly Colorimetric Nanofiber Design: Halochromic Sensors with Tunable pH‐Sensing Regime Based on 2‐Ethyl‐2‐Oxazoline and 2‐n‐Butyl‐2‐Oxazoline Statistical Copolymers Functionalized with Alizarin Yellow R
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Authors: De Meyer, T., Hemelsoet, K., Van Speybroeck, V., & De Clerck, K.
ORCID: Hemelsoet, Karen
Venue: Dyes and Pigments
Publisher: Elsevier BV
Published: 2014-03
Volume: 102
Pages: 241-250
ISSN: 0143-7208 (ISSN-L)
DOI: 10.1016/j.dyepig.2013.10.048
OpenAlex: W2100613765
Cited by: 107
References: 125
Citations by year: 2026: 5 · 2025: 11 · 2024: 10 · 2023: 12 · 2022: 8 · 2021: 15 · 2020: 10 · 2019: 9 · 2018: 6 · 2017: 4 · 2016: 9 · 2015: 6 · 2014: 2
FWCI: 4.07
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Dyes and Pigments (publishedVersion)
Ghent University Academic Bibliography (Ghent University) (submittedVersion, other-oa)
Funders: Fund for Scientific Research Flanders (FWO)
Research Board of Ghent University (BOF)
Topics: Physical Sciences › Chemical Engineering › Bioengineering › Analytical Chemistry and Sensors
Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
Keywords: acid-base indicators, halochromism, substituent effects, absorption spectra, pKa determination, proton affinity, pH sensitivity, dye design, textile sensors

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Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes

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