Abstract
Time and temperature are the crucial factors affecting the quality of perishable products. The device capable of recording temperature fluctuation and maintaining time has huge practical potential. In this research, a novel thermal history indicator (THI) was proposed based on covalent organic frameworks (COFs) with the irreversible color change performance. The color change and absorbance of the THI were investigated over a broad monitoring temperature range (− 22 ~ 55 ℃) and were closely correlated with its thermal accumulation over time and temperature. The activation energy (Ea) of the THI was calculated to be 55.31 kJ mol−1, which can be used to monitor the perishable products with deterioration reaction Ea ranging from 30.31 to 80.31 kJ mol−1. In addition, the THI also demonstrated the significant response to the environmental temperature fluctuations. Furthermore, the potential applications were evaluated by recording the changes of the THI gel and the total viable count (TVC) of food under the same conditions. The results indicated that the digital images of the colorimetric THI gel were correlated with TVC of food at 4 ℃ and 25 ℃, respectively. These results support that the proposed THI is potential for real-time, accurate, non-destructive, visually, and quantitatively monitoring food freshness during food supply chain distribution.
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The data that support the findings of this study are available on request from the corresponding author.
References
Adiani, V., Gupta, S., & Variyar, P. S. (2021). A simple time temperature indicator for real time microbial assessment in minimally processed fruits. Journal of Food Engineering, 311, 110731. https://doi.org/10.1016/j.jfoodeng.2021.110731
Ascherl, L., Evans, E. W., Gorman, J., Orsborne, S., Bessinger, D., Bein, T., & Auras, F. (2019). Perylene-based covalent organic frameworks for acid vapor sensing. Journal of the American Chemical Society, 141(39), 15693–15699. https://doi.org/10.1021/jacs.9b08079
Bag, S., Sasmal, H. S., Chaudhary, S. P., Dey, K., Blätte, D., Guntermann, R., & Banerjee, R. (2023). Covalent organic framework thin-film photodetectors from solution-processable porous nanospheres. Journal of the American Chemical Society, 145(3), 1649–1659. https://doi.org/10.1021/jacs.2c09838
Cencha, L. G., García, G. F., Budini, N., Urteaga, R., & Berli, C. L. (2022). Time-temperature indicator based on the variation of the optical response of photonic crystals upon polymer infiltration. Sensors and Actuators a: Physical, 341, 113571. https://doi.org/10.1016/j.sna.2022.113571
Chauvin, J. P. R., & Pratt, D. A. (2017). On the reactions of thiols, sulfenic acids, and sulfinic acids with hydrogen peroxide. Angewandte Chemie International Edition, 56(22), 6255–6259. https://doi.org/10.1002/anie.201610402
Chen, Y., Song, Y., Zhang, Z., Chen, Y., Deng, Q., & Wang, S. (2021). Thiol-functionalized covalent organic frameworks as thermal history indictor for temperature and time history monitoring. Advanced Functional Materials, 31(41), 2104885. https://doi.org/10.1002/adfm.202104885
Choi, S., Eom, Y., Kim, S. M., Jeong, D. W., Han, J., Koo, J. M., & Oh, D. X. (2020). A self-healing nanofiber-based self-responsive time-temperature indicator for securing a cold-supply chain. Advanced Materials, 32(11), 1907064. https://doi.org/10.1002/adma.202070083
Corradini, M. G. (2018). Shelf life of food products: From open labeling to real-time measurements. Annual Review of Food Science and Technology, 9, 251–269. https://doi.org/10.1146/annurev-food-030117-012433
Das, G., Garai, B., Prakasam, T., Benyettou, F., Varghese, S., Sharma, S. K., & Trabolsi, A. (2022). Fluorescence turn on amine detection in a cationic covalent organic framework. Nature Communications, 13(1), 3904. https://doi.org/10.1038/s41467-022-31393-2
Dodero, A., Escher, A., Bertucci, S., Castellano, M., & Lova, P. (2021). Intelligent packaging for real-time monitoring of food-quality: Current and future developments. Applied Sciences, 11(8), 3532. https://doi.org/10.3390/app11083532
Galliani, D., Mascheroni, L., Sassi, M., Turrisi, R., Lorenzi, R., Scaccabarozzi, A., & Beverina, L. (2015). Thermochromic latent-pigment-based time-temperature indicators for perishable goods. Advanced Optical Materials, 3(9), 1164–1168. https://doi.org/10.1002/adom.201500073
Gao, T., Tian, Y., Zhu, Z., & Sun, D. W. (2020). Modelling, responses and applications of time-temperature indicators (TTIs) in monitoring fresh food quality. Trends in Food Science & Technology, 99, 311–322. https://doi.org/10.1016/j.tifs.2020.02.019
Geng, K., He, T., Liu, R., Dalapati, S., Tan, K., Li, T., & Z., & Jiang, D. (2020). Covalent organic frameworks: Design, synthesis, and functions. Chemical Reviews, 120(16), 8814–8933. https://doi.org/10.1021/acs.chemrev.9b00550
Guo, L., Yang, L., Li, M., Kuang, L., Song, Y., & Wang, L. (2021). Covalent organic frameworks for fluorescent sensing: Recent developments and future challenges. Coordination Chemistry Reviews, 440, 213957. https://doi.org/10.1016/j.ccr.2021.213957
Huang, C., Shang, Y., Hua, J., Yin, Y., & Du, X. (2023). Self-destructive structural color liquids for time-temperature indicating. ACS Nano, 17(11), 10269–10279. https://doi.org/10.1021/acsnano.3c00467
Huang, S., Xiong, Y., Zou, Y., Dong, Q., Ding, F., Liu, X., & Li, H. (2019). A novel colorimetric indicator based on agar incorporated with Arnebia euchroma root extracts for monitoring fish freshness. Food Hydrocolloids, 90, 198–205. https://doi.org/10.1016/j.foodhyd.2018.12.009
Jhuang, J. R., Lin, S. B., Chen, L. C., Lou, S. N., Chen, S. H., & Chen, H. H. (2020). Development of immobilized laccase-based time temperature indicator by electrospinning zein fiber. Food Packaging and Shelf Life, 23, 100436. https://doi.org/10.1016/j.fpsl.2019.100436
Lee, J. H., Harada, R., Kawamura, S., & Koseki, S. (2018). Development of a novel time-temperature integrator/indicator (TTI) based on the Maillard reaction for visual thermal monitoring of the cooking process. Food and Bioprocess Technology, 11(1), 185–193. https://doi.org/10.1007/s11947-017-2003-3
Lehn, F., Goossens, Y., & Schmidt, T. (2023). Economic and environmental assessment of food waste reduction measures-Trialing a time-temperature indicator on salmon in HelloFresh meal boxes. Journal of Cleaner Production, 392, 136183. https://doi.org/10.1016/j.jclepro.2023.136183
Lin, C. Y., Zhang, D., Zhao, Z., & Xia, Z. (2018). Covalent organic framework electrocatalysts for clean energy conversion. Advanced Materials, 30(5), 1703646. https://doi.org/10.1002/adma.201703646
Liu, X., Huang, D., Lai, C., Zeng, G., Qin, L., Wang, H., & Chen, S. (2019). Recent advances in covalent organic frameworks (COFs) as a smart sensing material. Chemical Society Reviews, 48(20), 5266–5302. https://doi.org/10.1039/C9CS00299E
Luo, X., Zaitoon, A., & Lim, L. T. (2022). A review on colorimetric indicators for monitoring product freshness in intelligent food packaging: Indicator dyes, preparation methods, and applications. Comprehensive Reviews in Food Science and Food Safety, 21(3), 2489–2519. https://doi.org/10.1111/1541-4337.12942
Mataragas, M., Bikouli, V. C., Korre, M., Sterioti, A., & Skandamis, P. N. (2019). Development of a microbial time temperature indicator for monitoring the shelf life of meat. Innovative Food Science & Emerging Technologies, 52, 89–99. https://doi.org/10.1016/j.ifset.2018.11.003
Navrotskaya, A., Aleksandrova, D., Chekini, M., Yakavets, I., Kheiri, S., Krivoshapkina, E., & Kumacheva, E. (2022). Nanostructured temperature indicator for cold chain logistics. ACS Nano, 16(6), 8641–8650. https://doi.org/10.1021/acsnano.1c11421
Pawde, S. V., Chaudhari, S. R., & Matche, R. S. (2023). Micro perforation based smart label to guide freshness of pasteurized milk packet. Food Control, 151, 109783. https://doi.org/10.1016/j.foodcont.2023.109783
Rigg, D. J., Grabovac, I., Russo, S., Mestan, S. A., Pearce, P. J., Davidson, R. G., & Morris, C. E. M. (1987). A possible in-situ thermal history indicator for uncured film adhesives. The Journal of Adhesion, 22(1), 23–38. https://doi.org/10.1080/00218468708074984
Saenjaiban, A., Singtisan, T., Suppakul, P., Jantanasakulwong, K., Punyodom, W., & Rachtanapun, P. (2020). Novel color change film as a time-temperature indicator using polydiacetylene/silver nanoparticles embedded in carboxymethyl cellulose. Polymers, 12(10), 2306. https://doi.org/10.3390/polym12102306
Sakai, K., Lee, J. H., Kocharunchitt, C., Ross, T., Jenson, I., Koyama, K., & Koseki, S. (2020). Development of a Maillard reaction-based time-temperature integrator/indicator (TTI) for visual monitoring of chilled beef during long-term storage and distribution. Food and Bioprocess Technology, 13, 2094–2103. https://doi.org/10.1007/s11947-020-02549-z
Schilter, D. (2017). Thiol oxidation: A slippery slope. Nature Reviews Chemistry, 1(2), 0013. https://doi.org/10.1038/s41570-016-0013
Shou, W., Wang, Y., Yao, Y., Chen, L., Lin, B., Lin, Z., & Guoa, L. (2023). A two-dimensional disposable full-history time-temperature indicator for cold chain logistics. Analytica Chimica Acta, 1237, 340618. https://doi.org/10.1016/j.aca.2022.340618
Suppakul, P., Kim, D. Y., Yang, J. H., Lee, S. B., & Lee, S. J. (2018). Practical design of a diffusion-type time-temperature indicator with intrinsic low temperature dependency. Journal of Food Engineering, 223, 22–31. https://doi.org/10.1016/j.jfoodeng.2017.11.026
Tang, B., Wang, W., Hou, H., Liu, Y., Liu, Z., Geng, L., & Luo, A. (2022). A β-cyclodextrin covalent organic framework used as a chiral stationary phase for chiral separation in gas chromatography. Chinese Chemical Letters, 33(2), 898–902. https://doi.org/10.1016/j.cclet.2021.06.089
Wang, J., Feng, J., Lian, Y., Sun, X., Wang, M., & Sun, M. (2023). Advances of the functionalized covalent organic frameworks for sample preparation in food field. Food Chemistry, 405, 134818. https://doi.org/10.1016/j.foodchem.2022.134818
Wang, Q., Wu, Y., Guo, W., Zhang, F., & Zhang, F. (2022). A magnetic covalent organic framework as selective adsorbent for preconcentration of multi strobilurin fungicides in foods. Food Chemistry, 392, 133190. https://doi.org/10.1016/j.foodchem.2022.133190
Wang, Y. C., Lu, L., & Gunasekaran, S. (2017). Biopolymer/gold nanoparticles composite plasmonic thermal history indicator to monitor quality and safety of perishable bioproducts. Biosensors and Bioelectronics, 92, 109–116. https://doi.org/10.1016/j.bios.2017.01.047
Wu, J., Li, L., Cao, L., Liu, X., Li, R., & Ji, Y. (2023). Chirality-controlled mercapto-β-cyclodextrin covalent organic frameworks for selective adsorption and chromatographic enantioseparation. ACS Applied Materials & Interfaces, 15(22), 27214–27222. https://doi.org/10.1021/acsami.3c04066
Xia, T., Wu, Z., Liang, Y., Wang, W., Li, Y., Tian, X., & Chen, Q. (2023). Sulfonic acid functionalized covalent organic frameworks for lithium-sulfur battery separator and oxygen evolution electrocatalyst. Journal of Colloid and Interface Science, 645, 146–153. https://doi.org/10.1016/j.jcis.2023.04.115
Xin, J., Wang, X., Li, N., Liu, L., Lian, Y., Wang, M., & Zhao, R. S. (2020). Recent applications of covalent organic frameworks and their multifunctional composites for food contaminant analysis. Food Chemistry, 330, 127255. https://doi.org/10.1016/j.foodchem.2020.127255
Yang, Q., Luo, M., Liu, K., Cao, H., & Yan, H. (2020). Covalent organic frameworks for photocatalytic applications. Applied Catalysis B: Environmental, 276, 119174. https://doi.org/10.1016/j.apcatb.2020.119174
Yao, L., Rodriguez-Camargo, A., Xia, M., Mücke, D., Guntermann, R., Liu, Y., & Lotsch, B. V. (2022). Covalent organic framework nanoplates enable solution-processed crystalline nanofilms for photoelectrochemical hydrogen evolution. Journal of the American Chemical Society, 144(23), 10291–10300. https://doi.org/10.1021/jacs.2c01433
Ye, B., Chen, J., Ye, H., Zhang, Y., Yang, Q., Yu, H., & Wang, Y. (2022). Development of a time-temperature indicator based on Maillard reaction for visually monitoring the freshness of mackerel. Food Chemistry, 373, 131448. https://doi.org/10.1016/j.foodchem.2021.131448
Yu, Z., Jung, D., Park, S., Hu, Y., Huang, K., Rasco, B. A., & Chen, J. (2022). Smart traceability for food safety. Critical Reviews in Food Science and Nutrition, 62(4), 905–916. https://doi.org/10.1080/10408398.2020.1830262
Yue, C., Wang, J., Wu, D., Wang, Z., & Wang, G. (2023). Immobilization of phospholipase A1 on polyvinyl alcohol microspheres to develop a time-temperature indicator for freshness monitoring of pork. Journal of Food Engineering, 357, 111640. https://doi.org/10.1016/j.jfoodeng.2023.111640
Zhang, X., Sun, G., Xiao, X., Liu, Y., & Zheng, X. (2016). Application of microbial TTIs as smart label for food quality: Response mechanism, application and research trends. Trends in Food Science & Technology, 51, 12–23. https://doi.org/10.1016/j.tifs.2016.02.006
Zheng, Q., Huang, J., He, Y., Huang, H., Ji, Y., Zhang, Y., & Lin, Z. (2022). Single-crystalline covalent organic frameworks as high-performance liquid chromatographic stationary phases for positional isomer separation. ACS Applied Materials & Interfaces, 14(7), 9754–9762. https://doi.org/10.1021/acsami.1c20989
Zou, Y., Wu, J., Liu, G., Piron, M., Fedele, A., Antonio, S., & Manzardo, A. (2022). Examining the trade-offs in potential retail benefits of different expiration date modes: Insights into multidimensional scenarios. Resources, Conservation and Recycling, 186, 106511. https://doi.org/10.1021/acsami.1c20989
Funding
This work was supported by the National Natural Science Foundation of China under project no. 2190080961 and the Ministry of Science and Technology of China under project no. 2016YFD0401101.
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Hailin Xu: investigation, design of work, formal analysis, experiment, software, and writing the original draft; Yaru Guo: conceptualization, validation, supervision, and writing—review and editing; Shufang Zhou: formal analysis; Jiayi Wang: project administration and writing—review and editing; Futai Lu: supervision and funding acquisition; Shuo Wang: writing—review and editing; Qiliang Deng: conceptualization, writing—review and editing, funding acquisition, and supervision.
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Xu, H., Guo, Y., Zhou, S. et al. Colorimetric Covalent Organic Framework Gel as Thermal History Indicators for Food Freshness Monitoring. Food Bioprocess Technol (2024). https://doi.org/10.1007/s11947-024-03426-9
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DOI: https://doi.org/10.1007/s11947-024-03426-9