Abstract
Three vapochromic dyes named DiMo, MoMe, DiMe with different substituents were synthesized and investigated on their color change properties after exposure to 32 organic solvents after dyeing on cotton fabrics. The cotton-based sensor exhibited strong sensing properties to polar solvents rather than non-polar solvents. Especially, N,N-dimethylformamide detection was the best showing a color difference of 12.8 for DiMo, 21.4 for MoMe, and 25.8 for DiMe under 300 ppm exposure. Even at as low concentration as 10 ppm of N,N-dimethylformamide, the color change values were reached 7.3, 10.6, and 13.6 within an hour. The maximum absorption wavelength of the cotton-based sensor was shifted from 580 to 560, 570 to 560, and 560 to 540 nm, respectively, by the N,N-dimethylformamide exposure. The sensing mechanism was considered to depend on solvatochromism, aggregational properties of the dyes and adsorption amount of volatile organic compounds on textile substrates on which the dyes were applied. Finally, the reusability of the cotton-based sensor was tested for 10 cycles.
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Abdelrahman M, Fouda M, Ajarem J, Maodaa S, Allam A, Khattab T (2020) Development of colorimetric cotton swab using molecular switching hydrazine probe in calcium alginate. J Mol Struct 1216:128301–128309
Ahmed H, Khattab T, Mashaly H, El-Halwagy A, Rehan M (2020) Plasma activation toward multi-stimuli responsive cotton fabric via in situ development of polyaniline derivatives and silver nanoparticles. Cellulose 27:2913–2926. https://doi.org/10.1007/s10570-020-02980-7
Alaysuy O, Snari R, Aldawsari AA, A, Abu-Melha S, Khalifa M, El-Metwaly N, (2022) Development of green and sustainable smart biochromic and therapeutic bandage using red cabbage (Brassica oleracea L. Var. capitata) extract encapsulated into alginate nanoparticles. Int J Biol Macromol 211:390–399. https://doi.org/10.1016/j.ijbiomac.2022.05.062
Al-Qahtani S, Alzahrani H, Azher O, Owidah Z, Abualnaja M, Habeebullah T, El-Metwaly N (2021) Immobilization of anthocyanin-based red-cabbage extract onto cellulose fibers toward environmentally friendly biochromic diagnostic biosensor for recognition of urea. J Enviorn Chem Eng 9:105493–105502
Baumann W, Groebel B, Krayer M (1987) Determination of relative colour strength and residual colour difference by means of reflectance measurements. J Soc Dyers Colour 103:100–105. https://doi.org/10.1111/j.1478-4408.1987.tb01101.x
Beatty MA, Selinger AJ, Li Y, Hof F (2019) Parallel synthesis and screening of supramolecular chemosensors that achieve fluorescent turn-on detection of drugs in saliva. J Am Chem Soc 141:16763–16771. https://doi.org/10.1021/jacs.9b07073
Chen X, Yang M, Xu W, Qu Q, Zhao Q (2019) Broadly absorbing bluish black-to-transmissive sky blue electrochromic polymer based on 3,4-dioxythiophene. J Solid State Electrochem 23:19–25. https://doi.org/10.1007/s10008-018-4106-9
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 Pigments 124:249–257
El-Naggar M, Ali O, Saleh D, Abu-Saied M, Khattab T (2021) Preparation of green and sustainable colorimetric cotton assay using natural anthocyanins for sweat sensing. Int J Biol Macromol 190:894–903. https://doi.org/10.1016/j.ijbiomac.2021.09.049
Fairchild MD (2005) Color appearance models. John Wiley, Chichester, pp 183–195
Favaro G, Clementi C, Romani A, Vickackaite V (2007) Acidichromism and ionochromism of luteolin and apigenin, the main components of the naturally occurring yellow weld: A spectrophotometric and fluorimetric study. J Fluoresc 17:707–714. https://doi.org/10.1007/s10895-007-0222-0
Hau FK, Cheung K, Zhu N, Yarm VW (2019) Calixarene-based alkynyl-bridged gold(i) isocyanide and phosphine complexes as building motifs for the construction of chemosensors and supra molecular architectures. Org Chem Front 6:1205–1213. https://doi.org/10.1039/C9QO00258H
Hunt RWG (1991) Measuring colour. Ellis Horwood, New York, pp 71–77
Junaid H, Waseem M, Khan Z, Gul H, Yu C, Shaikh A, Shahzad S (2022) Fluorescent and colorimetric sensors for selective detection of TNT and TNP explosives in aqueous medium through fluorescence emission enhancement mechanism. J Photochem Photobiol A 428:113865–113879
Kasha M, Rawls H, El-Bayoumi M (1965) The exciton model in molecular spectroscopy. Pure Appl Chem 11:371–392. https://doi.org/10.1351/pac196511030371
Kim T, Lee S (2015a) Characteristics and application of the highly-durable and highly-sensitive super hydrophobic acid-gas sensing dye. Text Color Finish 27:105–112. https://doi.org/10.5764/TCF.2015.27.2.105
Kim T, Lee S (2015b) Synthesis and application of acid-gas sensing dyes having alkyl groups symmetrically substituted on monoazo chromophore. Fiber Polym 16:2106–2111
Kim E, Lee H, Ryu H, Park S, Kang S (2011) Cases series of malignant lymphohematopoietic disorder in Korean semiconductor industry. Saf Health Work 2:122–134. https://doi.org/10.5491/SHAW.2011.2.2.122
Koh J (2006) Alkali-clearable disperse dyeing of poly(ethyleneterephthalate) with azohydroxypyridone dyes containing a fluorosulfonyl group. Dyes Pigments 69:233–238. https://doi.org/10.1016/j.dyepig.2005.03.003
Kubota Y, Nakazawa M, Lee J, Naoi R, Tachikawa M, Inuzuka T, Funabiki K, Matsui M, Kim T (2021) Synthesis of near-infrared absorbing and fluorescent bis(pyrrol-2-yl)squaraines and their halochromic properties. Org Chem Front 8:6226–6243. https://doi.org/10.1039/D1QO01169C
Lee J, Kim T (2020) Synthesis of an acid-gas sensing fluorescence dye showing change of both color and fluorescence emission spectrum inside polyethylenic fiber on exposure to gas phase strong acid for application to washable textile sensors. Fiber Polym 21:2275–2284. https://doi.org/10.1007/s12221-020-1094-z
Lee J, Kim T (2021) Synthesis of novel coumarin-based acid vapochromic fluorescence dye showing change of both color and fluorescence emission spectrum for application to sensitive, reusable, and washable textile sensors. Text Res J 91:613–623. https://doi.org/10.1177/0040517520955232
Lee H, Kim E, Park J, Kang S (2011) Cancer mortality and incidence in Korean semiconductor workers. Saf Health Work 2:135–147. https://doi.org/10.5491/SHAW.2011.2.2.135
Lee J, Jun H, Kubota Y, Kim T (2021) Synthesis of red fluorescent dye with acid gas sensitive optical properties and fabrication of a washable and wearable textile sensor. Text Res J 91:2036–2052. https://doi.org/10.1177/0040517521994496
Liang Q, Zheng H, Yang D, Zheng X (2022) Atriphenylamine derivative and its Cd(II) complex with high-contrast mechanochromic luminescence and vapochromism. Cryst Eng Comm 24:543–551. https://doi.org/10.1037/d1ce01319j
Little AF, Christie RM (2016) Textile applications of commercial photochromic dyes. Part 6: photochromic polypropylene fibres. Color Technol 132:304–309
Manjakkal L, Dervin S, Dahiya R (2020) Flexible potentiometric pH sensors for wearable systems. RSC Adv 10:8594–8617. https://doi.org/10.1039/D0RA00016G
Ono T, Tsukiyama Y, Hatanaka S, Sakatsume Y, Ogoshi T, Hisaeda Y (2019) Inclusion crystals as vapochromic chemosensors: fabrication of a mini-sensor array for discrimination of small aromatic moecules based on side-chain engineering of naphthalenediimide derivatives. J Mater Chem C 7:9726–9734. https://doi.org/10.1039/C9TC03140E
Park H, Jang J, Shin J (2011) Quantitative exposure assessment of various chemical substances in a wafer fabrication industry facility. Saf Health Work 2:39–51. https://doi.org/10.5491/SHAW.2011.2.1.39
Park D, Heo J, Jeong W, Yoo Y, Park B, Kim J (2018) Smartphone-based VOC sensor using colorimetric polydiacetylenes. ACS Appl Mater Int 10:5014–5021. https://doi.org/10.1021/acsami/7b18121
Ribeiro LS, Pinto T, Monteiro A, Soares OSGP, Pereira C, Freire C, Pereira MFR (2013) Silica nanoparticles functionalized with a thermochromic dye for textile applications. J Mater Sci 48:5085–5092. https://doi.org/10.1007/s10853-013-7296-7
Shi B, Li W, Qin P, Zhao X, Qi X, Chai Y, Yang H, Qu W, Yao H, Zhang Y, Wei T, Lin Q (2022) A selective and stable vapochromic system constructed by pillar[5]arene-based host-guest interactions. Dyes Pigm 197:109885–109891
Wang X, Lin Q, Ramachandran S, Pembouong G, Pansu RB, Leray I, Lebental B, Zucchi G (2019) Optical chemosensors for metal ions in aqueous medium with polyfluorene derivatives: Sensitivity, selectivity and regeneration. Sens Actuators B Chem 286:521–532. https://doi.org/10.1016/j.snb.2019.01.013
Wenger O (2013) Vapochromism in organometallic and coordination complexes: Chemical sensors for volatile organic compounds. Chem Rev 113:3686–3733. https://doi.org/10.1021/cr300396p
Wurthner F, Saha-Moller KT, C, (2011) J-aggregates: From serendipitous discovery to supra-molecular engineering of functional dye materials. Angew Chem Int Ed 50:3376–3410. https://doi.org/10.1002/anie.201002307
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This paper was supported by Korea Institute for Advancement of Technology (KIAT) grant funded by the Korea Government (MOTIE) (P0012770, 2020 Professional human resources training project).
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Lee, J., Park, N. & Kim, T. Synthesis of VOC-sensing Dyes for Fabrication of Cotton-based Chromogenic Sensors. Cellulose 29, 8937–8956 (2022). https://doi.org/10.1007/s10570-022-04775-4
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DOI: https://doi.org/10.1007/s10570-022-04775-4