Abstract
Cotton fabrics with photodynamic performance (BP/CuPc-R/F) were prepared via a facile method and used as an effective photocatalytic system for wastewater treatment in this work. C.I. Reactive Blue 21 (a copper phthalocyanine derivative) and one kind of 3,3′,4,4′-benzophenone derivative (BPTCA) were covalently grafted onto cotton fabrics via conventional dyeing and finishing processes. The resultant photosensitive material (BP/CuPc-R/F) exhibited excellent hydroxyl-radical-generating activity under UVA light. Density functional theory calculation was used to investigate the photosensitizing mechanism and synergistic effect of copper phthalocyanine and benzophenone groups. BP/CuPc-R/F showed a stable activity in the decomposition of C.I. Reactive Black 5, and the degradation rate can still reach above 80% after 4 cycles. The degradation efficiency was enhanced in the condition of alkaline and high temperature (99% degradation at 45 °C in 10 min exposure). Furthermore, it also showed photo-induced antibacterial activity toward Staphylococcus aureus with bacterial reduction rate of 99.99% after 60 min of UVA light illumination. The photosensitive textile provides a facile and efficient approach for the removal of hazardous pollutants and microorganisms in water treatment.
Graphical abstract
Similar content being viewed by others
Data availability
The data in this article are reliable and are available from the corresponding author.
References
Ahmad I, Kan CW, Yao Z (2019) Photoactive cotton fabric for UV protection and self-cleaning. RSC Adv 9(32):18106–18114. https://doi.org/10.1039/c9ra02023c
Bhatt I, Tripathi BN (2011) Interaction of engineered nanoparticles with various components of the environment and possible strategies for their risk assessment. Chemosphere 82(3):308–317. https://doi.org/10.1016/j.chemosphere.2010.10.011
Bors W, Michel C, Saran M (1979) On the nature of biochemically generated hydroxyl radicals, Studies using the bleaching of p-nitrosodimethylaniline as a direct assay method. Eur J Biochem 95:621–627. https://doi.org/10.1111/j.1432-1033.1979.tb13003.x
Boyjoo Y, Sun H, Liu J, Pareek VK, Wang S (2016) A review on photocatalysis for air treatment: from catalyst development to reactor design. Chem Eng J 310:537–559. https://doi.org/10.1016/j.cej.2016.06.090
Carducci A, Federigi I, Liu D, Thompson JR, Marco V (2020) Making waves: coronavirus detection, presence and persistence in the water environment: state of the art and knowledge needs for public health. Water Res 179:115907. https://doi.org/10.1016/j.watres.2020.115907
Chen X, Ng D (2021) β-Cyclodextrin-conjugated phthalocyanines as water-soluble and recyclable sensitisers for photocatalytic applications. Chem Comm 57:3567–3570. https://doi.org/10.1039/d1cc00713k
Dingenen F, Blommaerts N, Van Hal M, Borah R, Arenas-Esteban D, Lenaerts S, Bals S, Verbruggen SW (2021) Layer-by-layer-stabilized plasmonic gold-silver nanoparticles on TiO2: towards stable solar active photocatalysts. Nanomaterials 11(10):2624. https://doi.org/10.3390/nano11102624
Dong S, Cui L, Zhang W, Xia L, Zhou S, Russell CK, Fan M, Feng J, Sun J (2020) Double-shelled ZnSnO3 hollow cubes for efficient photocatalytic degradation of antibiotic wastewater. Chem Eng J 384:123279. https://doi.org/10.1016/j.cej.2019.123279
Fessi N, Nsib MF, Chevalier Y, Guillard C, Dappozze F, Houas A, Palmisano L, Parrino F (2019) Photocatalytic degradation enhancement in pickering emulsions stabilized by solid particles of bare TiO2. Langmuir 35(6):2129–2136. https://doi.org/10.1021/acs.langmuir.8b03806
Gao A, Zhang H, Sun G, Xie K, Hou A (2017) Light-induced antibacterial and UV-protective properties of polyamide 56 biomaterial modified with anthraquinone and benzophenone derivatives. Mater Des 130:215–222. https://doi.org/10.1016/j.matdes.2017.05.071
Han J, Zhu Z, Li N, Chen D, Lu J (2021) Metalloporphyrin-based D-A type conjugated organic polymer nanotube for efficient photocatalytic degradation. Appl Catal B-Environ 291:120108. https://doi.org/10.1016/j.apcatb.2021.120108
Hou A, Zhou M, Wang X (2009) Preparation and characterization of durable antibacterial cellulose biomaterials modified with triazine derivatives. Carbohydr Polym 75:328–332. https://doi.org/10.1016/j.carbpol.2008.07.032
Hou A, Chen B, Dai J, Zhang K (2010) Using supercritical carbon dioxide as solvent to replace water in polyethylene terephthalate (PET) fabric dyeing procedures. J Clean Prod 18:1009–1014. https://doi.org/10.1016/j.jclepro.2010.03.001
Hou A, Feng G, Zhuo J, Sun G (2015) UV light-induced generation of reactive oxygen species and antimicrobial properties of cellulose fabric modified by 3,3′,4,4′-benzophenone tetracarboxylic acid. ACS Appl Mater Interfaces 7(50):27918–27924. https://doi.org/10.1021/acsami.5b09993
Hou J, Wang Y, Zhou J, Lu Y, Liu Y, Lv X (2021) Photocatalytic degradation of methylene blue using a ZnO/TiO2 heterojunction nanomesh electrode. Surf Interfaces 22:100889. https://doi.org/10.1016/j.surfin.2020.100889
Hu L, Zhang H, Gao A, Hou A (2018) Functional modification of cellulose fabrics with phthalocyanine derivatives and the UV light-induced antibacterial performance. Carbohydr Polym 201:382–386. https://doi.org/10.1016/j.carbpol.2018.08.087
Hu L, Hou A, Xie K, Gao A (2019) Light-induced production of reactive oxygen species by a novel water-soluble benzophenone derivative containing quaternary ammonium groups and it’s assembly on the protein fiber surface. ACS Appl Mater Interfaces 11(29):26500–26506. https://doi.org/10.1021/acsami.9b07992
Huang S, Xu Y, Liu Q, Zhou T, Zhao Y, Jing L, Xu H, Li H (2017) Enhancing reactive oxygen species generation and photocatalytic performance via adding oxygen reduction reaction catalysts into the photocatalysts. Appl Catal B-Environ 218:174–185. https://doi.org/10.1016/j.apcatb.2017.06.030
Jv X, Zhao X, Ge H, Sun J, Li H, Wang Q, Lu H (2019) Fabrication of a magnetic poly(aspartic acid)-poly(acrylic acid) hydrogel: application for the adsorptive removal of organic dyes from aqueou solution. J Chem Eng Data 64(3):1228–1236. https://doi.org/10.1021/acs.jced.8b01117
Klausen M, Ucuncu M, Bradley M (2020) Design of photosensitizing agents for targeted antimicrobial photodynamic therapy. Molecules 25:5239. https://doi.org/10.3390/molecules25225239
Ma D, Yi H, Lai C, Liu X, Yang L (2021) Critical review of advanced oxidation processes in organic wastewater treatment. Chemosphere 275(3):130104. https://doi.org/10.1016/j.chemosphere.2021.130104
Marin ML, Santos-Juanes L, Arques A, Amat AM, Miranda MA (2012) Organic photocatalysts for the oxidation of pollutants and model compounds. Chem Rev 112(3):1710–1750. https://doi.org/10.1021/cr2000543
Mohyudin S, Farooq R, Jubeen F, Rasheed T, Fatima M, Sher F (2021) Microbial fuel cells a state-of-the-art technology for wastewater treatment and bioelectricity generation. Environ Res 204:112387. https://doi.org/10.1016/j.envres.2021.112387
Mondal B, Bairagi D, Nandi N, Hansda B, Das KS, Edwards-Gayle C, Castelletto V, Hamley IW, Banerjee A (2020) Peptide-based gel in environmental remediation: removal of toxic organic dyes and hazardous Pb2+ and Cd2+ ions from wastewater and oil spill recovery. Langmuir 36(43):12942–12953. https://doi.org/10.1021/acs.langmuir.0c02205
Pan Z, Song C, Li L, Wang H, Pan Y, Wang C, Li J, Wang T, Feng X (2019) Membrane technology coupled with electrochemical advanced oxidation processes for organic wastewater treatment: recent advances and future prospects. Chem Eng J 376:120909. https://doi.org/10.1016/j.cej.2019.01.188
Pazdzior K, Bilinska L, Ledakowicz S (2019) A review of the existing and emerging technologies in the combination of AOPs and biological processes in industrial textile wastewater treatment. Chem Eng J 376:120597. https://doi.org/10.1016/j.cej.2018.12.057
Qi L, Gong Y, Fang M, Jia Z, Cheng N, Yu L (2020) Surface-active ionic-liquid-encapsulated polyoxometalate nanospheres: construction, self-assembly, adsorption behavior, and application for dye removal. ACS Appl Nano Mater 3(1):375–383. https://doi.org/10.1021/acsanm.9b02012
Ren A, Zahid A, Fan D, Yang X, Imran MA, Alomainy A, Abbasi QH (2019) State-of-the-art in terahertz sensing for food and water security-a comprehensive review. Trends Food Sci Tech 85:241–251. https://doi.org/10.1016/j.tifs.2019.01.019
Sathe SM, Chakraborty I, Dubey BK, Ghangrekar MM (2022) Microbial fuel cell coupled Fenton oxidation for the cathodic degradation of emerging contaminants from wastewater: applications and challenges. Environ Res 204:112135. https://doi.org/10.1016/j.envres.2021.112135
Shen J, Steinbach R, Tobin J, Nakata MM, Bower M, Mccoustra M, Bridle H, Arrighi V, Vilela F (2016) Photoactive and metal-free polyamide-based polymers for water and wastewater treatment under visible light irradiation. Appl Catal B- Environ 193:226–233. https://doi.org/10.1016/j.apcatb.2016.04.015
Shi T, Li H, Ding L, You F, Ge L, Liu Q, Wang K (2019) Facile preparation of unsubstituted iron(II) phthalocyanine/carbon nitride nanocomposites: a multipurpose catalyst with reciprocally enhanced photo/electrocatalytic activity. ACS Sustain Chem Eng 7(3):3319–3328. https://doi.org/10.1021/acssuschemeng.8b05366
Shkrob IA Jr, Sauer MC (2004) Hole scavenging and photo-stimulated recombination of electron-hole pairs in aqueous TiO2 nanoparticles. J Phys Chem B 108(33):12497–12511. https://doi.org/10.1021/jp047736t
Song J, Deng Q, Huang M, Kong Z (2022) Carbon nanotube enhanced membrane distillation for salty and dyeing wastewater treatment by electrospinning technology. Environ Res 204:111892. https://doi.org/10.1016/j.envres.2021.111892
Sun H, Tian X, Wang J, Zhang J, Yuan Y, Sun Z (2011) Theoretical studies on molecular and structures of mono- and binuclear chromium carbazole derivatives for optoelectronics. J Phys Chem A 115(50):14495–14501. https://doi.org/10.1021/jp2066452
Sun M, An J, Pan Z, Feng G, Fan X, Song C, Wang T (2021) Enhanced organic wastewater treatment performance in electrochemical filtration process of coal-based carbon membrane via the simple Fe2+ addition. Sep Purif Tech 276:119418. https://doi.org/10.1016/j.seppur.2021.119418
Wang J, Wang S (2020) Reactive species in advanced oxidation processes: formation, identification and reaction. Chem Eng J 401:126158. https://doi.org/10.1016/j.cej.2020.126158
Wang X, Li Z, Zhang Y, Li Q, Du H, Liu F, Zhang X, Mu H, Duan J (2022) Enhanced photocatalytic antibacterial and degradation performance by p-n-p type CoFe2O4/CoFe2S4/MgBi2O6 photocatalyst under visible light irradiation. Chem Eng J 429:132270. https://doi.org/10.1016/j.cej.2021.132270
Wu B, Li Y, Su K, Tan L, Liu X, Cui Z, Yang X, Liang Y, Li Z, Zhu S (2019) The enhanced photocatalytic properties of MnO2/g-C3N4 heterostructure for rapid sterilization under visible light. J Hazard Mater 377:227–236. https://doi.org/10.1016/j.jhazmat.2019.05.074
Xie K, Yu Y, Shi Y (2009) Synthesis and characterization of cellulose/silica hybrid materials with chemical crosslinking. Carbohydr Polym 78:799–805. https://doi.org/10.1016/j.carbpol.2009.06.019
Xie K, Zhao W, He X (2011) Adsorption properties of nano-cellulose hybrid containing polyhedral oligomeric silsesquioxane and removal of reactive dyes from aqueous solution. Carbohydr Polym 83:1516–1520. https://doi.org/10.1016/j.carbpol.2010.09.064
Yamaguchi M, Abe H, Ma T, Tadaki D, Niwano M (2020) Bactericidal activity of TiO2 nanotube thin films on Si by photocatalytic generation of active oxygen species. Langmuir 36(42):12668–12677. https://doi.org/10.1021/acs.langmuir.0c02225
Yang W, Zhao J, Sonn C, Escudero D, Karatay A, Yaglioglu H, Küçüköz B, Hayvali M, Li C, Jacquemin D (2016) Efficient intersystem crossing in heavy-atom-free perylenebisimide derivatives. J Phys Chem C 120(19):10162–10175. https://doi.org/10.1021/acs.jpcc.6b01584
Yang H, Liu Z, Wang K, Pu S, Yang S, Yang L (2017) A facile synthesis of TiO2-CdS heterostructures with enhanced photocatalytic activity. Catal Letters 147:2581–2591. https://doi.org/10.1007/s10562-017-2151-0
Yi S, Zou Y, Sun S, Dai F, Si Y, Sun G (2018) Rechargeable photoactive silk-derived nanofibrous membranes for degradation of Reactive Red 195. ACS Sustain Chem Eng 7(1):986–993. https://doi.org/10.1021/acssuschemeng.8b04646
Yi S, Sun S, Fan Y, Zou Y, Dai F, Si Y (2020a) Scalable fabrication of rechargeable photoactive cellulose nanofibrous membranes for efficient degradation of dyes. Cellulose 27(9):5285–5296. https://doi.org/10.1007/s10570-020-03168-9
Yi S, Wu Y, Zhang Y, Zou Y, Dai F, Si Y (2020b) Antibacterial activity of photoactive silk fibroin/cellulose acetate blend nanofibrous membranes against Escherichia coli. ACS Sustain Chem Eng 8:16775–16780. https://doi.org/10.1021/acssuschemeng.0c04276
Zhang M, Shao C, Guo Z, Zhang Z, Mu J (2011) Hierarchical nanostructures of copper(II) phthalocyanine on electrospun TiO2 nanofibers: controllable solvothermal-fabrication and enhanced visible photocatalytic properties. ACS Appl Mater Interfaces 3(2):369–377. https://doi.org/10.1021/am100989a
Zhang H, Wang J, Xie K, Pei L, Hou A (2020a) Synthesis of novel green reactive dyes and relationship between their structures and printing properties. Dyes Pigm 174:108079. https://doi.org/10.1016/j.dyepig.2019.108079
Zhang X, Li Z, Lin S, Théato P (2020b) Fibrous materials based on polymeric salicyl active esters as efficient adsorbents for selective removal of anionic dye. ACS Appl Mater Interfaces 12(18):21100–21113. https://doi.org/10.1021/acsami.0c03039
Zhao Y, Li Y, Sun L (2021) Recent advances in photocatalytic decomposition of water and pollutants for sustainable application. Chemosphere 276:130201. https://doi.org/10.1016/j.chemosphere.2021.130201
Funding
This work was supported by National Natural Science Foundation of China (Grant No. 22208310); Opening Project of Key Laboratory of Clean Dyeing and Finishing Technology of Zhejiang Province (Grant No. QJRZ2202 and QJRZ2204); Research Start-up Funding of Zhejiang Sci-Tech University (Grant No. 21202301-Y); and Postdoctoral Fellowship of Zhejiang Province (Grant No. ZJ2021109).
Author information
Authors and Affiliations
Contributions
LH: Methodology, Software, Investigation, Writing-Original Draft, Funding acquisition; ML: Methodology, Project administration, Funding acquisition; XS: Software, Data curation; KX: Writing-Review & Editing, Data Curation; AH: Methodology, Writing—Review & Editing, Resources.
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no known competing financial interests or personal relationships that had appeared to influence the work reported in this paper.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Hu, L., Song, X., Li, M. et al. Scalable fabrication of benzophenone/phthalocyanine-decorated photodynamic cotton fabrics for enhanced dye degradation and antibacterial performance. Cellulose 30, 4683–4696 (2023). https://doi.org/10.1007/s10570-023-05141-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-023-05141-8