Abstract
Sulfonphthaleine dyes are important class of pH indicators with some applications in novel sensors. In this paper, the authors present a theoretical study to elucidate the effect of physical factors on the halochromic behavior of the sulfonphthaleine dyes. The studied sulfonphthaleine dyes are phenol red, cresol red, bromophenol blue and the physical factors such as temperature, pressure, dielectric constant of solvent and isotope type of constituent atoms are taken into account. In the meantime, changes of pH of the color change of the indicators, ∆pH, with the physical factors in the acid–base equilibrium of the indicators are studied. To this end, Enthalpy change, ∆Ha, entropy change, ∆Sa, Gibbs free energy change, ∆Ga, and equilibrium constant of ionization process of indicators, Ka, are calculated for the equilibrium reaction under different conditions; then their values are interpreted by the laws of thermodynamics and statistical thermodynamics. The results show that ∆pH is positive by increasing temperature at any pressure, increasing pressure at any temperature, decreasing the polarity of the solvent used, and using isotopes of constituent atoms. The effect of temperature and pressure on ∆pH is lower respectively under higher temperatures and pressures, and it is not dependent on the indicator type. The ∆pH values due to the isotopic factor depend on the type of atom as well as that of the indicator. These findings indicate the importance of physical factors on the halochromic behavior of dyes for further research and the development of pH-sensitive sensors.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bamfield P (2001) Chromic phenomena, technological applications of colour chemistry, 1st edn. Cambridge, Royal Society of Chemistrys
Barachevskii VA, Kobeleva OI, Valova TM, Ait AO, Kol’tsova LS, Shienok AI, Zaichenko NL, Laptev AV, Khodonov AA, Yu Kuznetsova O, Dudinov AA, Lichitskii BV, Krayushkin MM (2012) Spectral indications of interaction of functionalized photochromic compounds with Ag and Au nanoparticles. Theor Exp Chem 48:14–20. https://doi.org/10.1007/s11237-012-9236-z
Bateman AS, Kelly SD, Jickells TD (2005) Nitrogen Isotope Relationships between crops and fertilizer: implications for using nitrogen isotope analysis as an indicator of agricultural regime. J Agr Food Chem 53:5760–5765. https://doi.org/10.1021/jf050374h
Byrne RH, Breland JA (1989) High-precision multiwavelength pH determinations in seawater using cresol red. Deep Sea Res Pt A Oceanograph Res Pap 36:803–810. https://doi.org/10.1016/0198-0149(89)90152-0
Chang Y, Bai H, Li S, Kuo C (2011) Bromocresol green/mesoporous silica adsorbent for ammonia gas sensing via an optical sensing instrument. Sensors 11:4060–4072. https://doi.org/10.3390/s110404060
Chen W, Lin XH, Huang LY, Luo HB (2005) Electrochemical characterization of polymerized cresol red film modified glassy carbon electrode and separation of electrocatalytic responses for ascorbic. Microchim Acta 151:101–107. https://doi.org/10.1007/s00604-005-0376-x
Clayton TD, Byrne RH (1993) Spectrophotometric seawater pH measurements: total hydrogen ion concentration scale calibration of m-cresol purple and at-sea results. Deep Sea Res Pt I Oceanograp Res Pap 40:2115–2129. https://doi.org/10.1016/0967-0637(93)90048-8
Cossi M, Rega N, Scalmani G, Barone V (2003) Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comput Chem 24:669–681. https://doi.org/10.1002/jcc.10189
De Meyer T, Hemelsoet K, Van Speybroeck V, De Clerck K (2014) Substituent effects on absorption spectra of pH indicators: an experimental and computational study of sulfonphthaleine dyes. Dyes Pigm 102:241–250. https://doi.org/10.1016/j.dyepig.2013.10.048
De Meyer T, Steyaert I, Hemelsoet K, Hoogenboom R, Van Speybroeck V, De Clerck K (2016) Halochromic properties of sulfonphthaleine dyes in a textile environment: the influence of substituents. Dyes Pigm 124:249–257. https://doi.org/10.1016/j.dyepig.2015.09.007
Ensafi AA, Dadkhah-Tehrani S, Karimi-Maleh H (2010) Poly(xylenol blue) modified multiwall carbon nanotubes-glassy carbon electrode for simultaneous determination of ascorbic acid, epinephrine, and uric acid by differential pulse voltammetry. In: International Conference on Enabling science and nanotechnology, Kuala Lumpur, Malaysia. https://doi.org/10.1109/ESCINANO.2010.5700983
Flores R (1978) A rapid and reproducible assay for quantitative estimation of proteins using bromophenol blue. Anal Biochem 88:605–611. https://doi.org/10.1016/0003-2697(78)90462-1
Frisch MJ et al (2004) Gaussian 03, Revision C.02. Gaussian, Inc., Wallingford
Gibson LT, Ewlad-Ahmed A, Knight B, Horie V, Mitchell G, Robertson CJ (2012) Measurement of volatile organic compounds emitted in libraries and archives: an inferential indicator of paper decay. Chem Cent J 6:42. https://journal.chemistrycentral.com/content/6/1/42
Ghanadzadeh Gilani A, Taghvaei V, Moradi Rufchahi E, Mirzaei M (2017) Photo-physical and structural studies of some synthesized arylazoquinoline dyes. Spectrochim Acta A 185:111–124. https://doi.org/10.1016/j.saa.2017.05.035
Golchoubian H, Mehrbanian D, Rezaee E, Xu ZX (2019) Structural and chromotropism properties of copper(II) complexes with 3,3′-((pyridin-2-ylmethyl)azanediyl)dipropanamide ligand. Transit Metal Chem 44:671–680
Hermosilla L, Caroli Rezende M, Gageiro Machado V, Stock RI (2017) Thermohalochromism of phenolate dyes conjugated with nitro-substituted aryl groups. Spectrochim Acta A 173:556–561. https://doi.org/10.1016/j.saa.2016.10.017
Hosseini M, Heydari R, Alimoradi M (2014) A novel pH optical sensor using methyl orange based on triacetylcellulose membranes as support. Spectrochim Acta A 128:864–867. https://doi.org/10.1016/j.saa.2014.02.171
Hua X, Hou X, Gong X, Shen G (2013) Electrochemical behaviour of 5-fluorouracil on glassy carbon electrode modified with bromothymol blue and multiwalled carbon nanotubes. Anal Methods 5:2470–2476
Kelly FM, Cochrane C (2015) Color-changing textiles and electrochromism. In: Tao X (ed) Handbook of smart textiles. Springer, Singapore, pp 859–889. https://doi.org/10.1007/978-981-4451-45-1_16
Kim S (2006) Functional dyes. Elsevier, Amsterdam
Kulinich AV, Ishchenko AA (2019) Structures and fluorescence spectra of merocyanine dyes in polymer films. J App Spectrosc 86:35–42. https://doi.org/10.1007/s10812-019-00777-6
Kulinich AV, Ishchenko AA, Bondarev SL, Sukhodola AA (2018) Effect of temperature on the spectral fluorescent properties of positively solvatochromic merocyanines. Theor Exp Chem 54:331–338. https://doi.org/10.1007/s11237-018-9578-2
Kurzweilová H, Sigler K (1993) Fluorescent staining with bromocresol purple: a rapid method for determining yeast cell dead count developed as an assay of killer toxin activity. Yeast 9:1207–1211. https://doi.org/10.1002/yea.320091107
Marona H, Schapoval E (2001) Spectrophotometric determination of sparfloxacin in pharmaceutical formulations using bromothymol blue. J Pharm Biomed Anal 26:501–504. https://doi.org/10.1016/s0731-7085(01)00429-0
Matějec V, Barton I, Pospisilova M, Traplova L (2019) Extrinsic fiber-optic sensor for detection of saliva pH. Chem Afr 2:301–307. https://doi.org/10.1007/s42250-019-00050-5
Mineo PG, Vento F, Abbadessa A, Scamporrino E, Nicosia A (2019) An optical sensor of acidity in fuels based on a porphyrin derivative. Dyes Pigm 161:147–154. https://doi.org/10.1016/j.dyepig.2018.09.045
Nakamura N, Amao Y (2003) An optical sensor for CO2 using thymol blue and europium (III) complex composite film. Sens Actuators B 92:98–101. https://doi.org/10.1016/S0925-4005(03)00098-4
Özyiğitoğlu G (2020) use of Lichens in biological monitoring of air quality. Environ Concerns Sust Develop. https://doi.org/10.1007/978-981-13-5889-0_3
Steyaert I, Rahier H, De Clerck K (2015) Nanofibre-based sensors for visual and optical monitoring. NanoSci Technol 96:157–177. https://doi.org/10.1007/978-3-319-14406-1_7
Sun X, Branford-White C, Yu ZW, Zhu LM (2015) Development of universal pH sensors based on textiles. J Solgel Sci Technol 74:641–649. https://doi.org/10.1007/s10971-015-3643-2
Surati PR, Shah BA (2015) Photochromic and molecular switching behaviour of Schiff base-containing pyrazolone ring. Chem Pap 69:368–375. https://doi.org/10.1515/chempap-2015-0021
Tomasi J, Persico M (1994) Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent. Chem Rev 94:2027–2094. https://doi.org/10.1021/cr00031a013
Van der Schueren L, Hemelsoet K, Van Speybroeck V, De Clerck K (2012) The influence of a polyamide matrix on the halochromic behaviour of the pH-sensitive azo dye Nitrazine Yellow. Dyes Pigm 94:443–451. https://doi.org/10.1016/j.dyepig.2012.02.013
Yang G, Yan J, Qi F, Sun C (2010) 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. Electroanal 22:2729–2738. https://doi.org/10.1002/elan.201000260
Yao W, Byrne R (2001) Spectrophotometric determination of freshwater pH using bromocresol purple and phenol red. Environ Sci Technol 35:1197–1201. https://doi.org/10.1021/es001573e
Zhang L, Li Z, Chang R, Chen Y, Zhang W (2009) Synthesis and characterization of novel phenolphthalein immobilized halochromic fiber. React Funct Polym 69:234–239. https://doi.org/10.1016/j.reactfunctpolym.2009.01.001
Zollinger H (2003) Color chemistry: synthesis, properties, and applications of organic dyes and pigments. VHCA en, WILEY-VCH
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Mojbafan, M., Zanjanchi, F. & Taherkhani, M. The influence of physical factors on the halochromic behavior of the pH-sensitive sulfonphthaleine dyes: a DFT study. Chem. Pap. 74, 4355–4363 (2020). https://doi.org/10.1007/s11696-020-01239-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-020-01239-6