Abstract
Advanced multifunctional composite materials have been a significant force in the advancement of efficient solar-thermal energy conversion and storage, which is critical to address current energy shortage problems. In this study, novel phase change material (PCM) composite fiber films, composed of Py-CH (one novel pyrene-based aggregation-induced emission luminogen (AIEgen))/polyvinyl pyrrolidone (PVP)/polyethylene glycol (PEG), have been produced by electrospinning technology with PEG as the phase change material. The combination of AIE and twist intermolecular charge transfer (TICT) characteristics of Py-CH together with the water absorption performance of PVP afforded a temperature-dependent fluorescence change. On increasing the temperature from 30 to 160 °C, the APP (pyrene-based AIEgen/PVP/PEG) composites exhibit a blue-shifted emission with a color changed from green-yellow to cyan, from cyan to blue, and finally, to purple. Furthermore, the entanglement of the macromolecular chains and distinctive porous structure between PVP and PEG played a significant role in preventing the leakage and transfer issues of PEG. Therefore, the composite fiber films with a PEG content of 60% exhibited latent heat in the range of 79~89 J/g and were extremely stable for up to 100 heating-cooling cycles. As a result, the application of these APP composites could be further promoted to solar energy conversation and storage, high-temperature warning, and anti-counterfeiting applications. Hence, composite materials containing the pyrene-based AIEgen and phase change materials have opened up new avenues for the possible application of such materials in thermal energy storage.
Graphical Abstract
Similar content being viewed by others
References
Bai H, Li C, Shi G (2011) Functional composite materials based on chemically converted graphene. Adv Mater 23:1089–1115. https://doi.org/10.1002/adma.201003753
Cao Y, Weng M, Mahmoud M et al (2022) Flame-retardant and leakage-proof phase change composites based on MXene/polyimide aerogels toward solar thermal energy harvesting. Adv Compos Hybrid Mater 5:1253–1267. https://doi.org/10.1007/s42114-022-00504-4
Xu D, Huang G, Guo L et al (2022) Enhancement of catalytic combustion and thermolysis for treating polyethylene plastic waste. Adv Compos Hybrid Mater 1–17. https://doi.org/10.1007/s42114-021-00317-x
Liu C, Huang Q, Zheng K et al (2020) Impact of lithium salts on the combustion characteristics of electrolyte under diverse pressures. Energies 13:5373. https://doi.org/10.3390/en13205373
Cao Y, Zeng Z, Huang D et al (2022) Multifunctional phase change composites based on biomass/MXene-derived hybrid scaffolds for excellent electromagnetic interference shielding and superior solar/electro-thermal energy storage. Nano Res 15:8524–8535. https://doi.org/10.1007/s12274-022-4626-6
Huang D, Chen Y, Zhang L et al (2023) Flexible thermoregulatory microcapsule/polyurethane-MXene composite films with multiple thermal management functionalities and excellent EMI shielding performance. J Mater Sci Technol. https://doi.org/10.1016/j.jmst.2023.05.013
Da Cunha JP, Eames P (2016) Thermal energy storage for low and medium temperature applications using phase change materials–a review. Appl Energy 177:227–238. https://doi.org/10.1016/j.apenergy.2016.05.097
Shen R, Weng M, Zhang L et al (2022) Biomass-based carbon aerogel/Fe3O4@ PEG phase change composites with satisfactory electromagnetic interference shielding and multi-source driven thermal management in thermal energy storage. Compos - A: Appl Sci Manuf 163:107248. https://doi.org/10.1016/j.compositesa.2022.107248
Yuan K, Shi J, Aftab W et al (2020) Engineering the thermal conductivity of functional phase-change materials for heat energy conversion, storage, and utilization. Adv Func Mater 30:1904228. https://doi.org/10.1002/adfm.201904228
Huang X, Alva G, Jia Y et al (2017) Morphological characterization and applications of phase change materials in thermal energy storage: a review. Renew Sustain Energy Rev 72:128–145. https://doi.org/10.1016/j.rser.2017.01.048
Zhu C, Lu X, Wu H et al (2022) Constructing heat conduction path and flexible support skeleton for PEG-based phase change composites through salt template method. Compos Sci Technol 226:109532. https://doi.org/10.1016/j.compscitech.2022.109532
Mohamed NH, Soliman FS, El Maghraby H et al (2017) Thermal conductivity enhancement of treated petroleum waxes, as phase change material, by α nano alumina: energy storage. Renew Sustain Energy Rev 70:1052–1058. https://doi.org/10.1016/j.rser.2016.12.009
Luo R, Wang L, Yu W et al (2023) High energy storage density titanium nitride-pentaerythritol solid–solid composite phase change materials for light-thermal-electric conversion. Appl Energy 331:120377. https://doi.org/10.1016/j.apenergy.2022.120377
Liu Y, Yang H, Wang Y et al (2021) Fluorescent thermochromic wood-based composite phase change materials based on aggregation-induced emission carbon dots for visual solar-thermal energy conversion and storage. Chem Eng J 424:130426. https://doi.org/10.1016/j.cej.2021.130426
Chen C, Wang L, Huang Y (2007) Electrospinning of thermo-regulating ultrafine fibers based on polyethylene glycol/cellulose acetate composite. Polymer 48:5202–5207. https://doi.org/10.1016/j.polymer.2007.06.069
Meng Y, Zhao Y, Zhang Y et al (2020) Induced dipole force driven PEG/PPEGMA form-stable phase change energy storage materials with high latent heat. Chem Eng J 390:124618. https://doi.org/10.1016/j.cej.2020.124618
Gao H, Bing N, Bao Z et al (2023) Sandwich-structured MXene/wood aerogel with waste heat utilization for continuous desalination. Chem Eng J 454:140362. https://doi.org/10.1016/j.cej.2022.140362
Sundararajan S, Samui AB, Kulkarni PS (2017) Versatility of polyethylene glycol (PEG) in designing solid–solid phase change materials (PCMs) for thermal management and their application to innovative technologies. J Mater Chem A 5:18379–18396. https://doi.org/10.1039/C7TA04968D
Wu B, Lao D, Fu R et al (2020) Novel PEG/EP form-stable phase change materials with high thermal conductivity enhanced by 3D ceramics network. Ceram Int 46:25285–25292. https://doi.org/10.1016/j.ceramint.2020.06.321
Ji R, Zhang Q, Zhou F et al (2021) Electrospinning fabricated novel poly (ethylene glycol)/graphene oxide composite phase-change nano-fibers with good shape stability for thermal regulation. J Energy Storage 40:102687. https://doi.org/10.1016/j.est.2021.102687
Huang J, Su J, Xu W et al (2022) High enthalpy efficiency lignin-polyimide porous hybrid aerogel composite phase change material with flame retardancy for superior solar-to-thermal energy conversion and storage. Sol Energy Mater Sol Cells 248:112036. https://doi.org/10.1016/j.solmat.2022.112036
Sheng X, Dong D, Lu X et al (2020) MXene-wrapped bio-based pomelo peel foam/polyethylene glycol composite phase change material with enhanced light-to-thermal conversion efficiency, thermal energy storage capability and thermal conductivity. Compos - A: Appl Sci Manuf 138:106067. https://doi.org/10.1016/j.compositesa.2020.106067
Xia Q, Zhang Y, Li Y et al (2022) A historical review of aggregation-induced emission from 2001 to 2020: a bibliometric analysis. Aggregate 3:e152. https://doi.org/10.1002/agt2.152
Islam MM, Hu Z, Wang Q et al (2019) Pyrene-based aggregation-induced emission luminogens and their applications. Mater Chem Front 3:762–781. https://doi.org/10.1039/C9QM00090A
Xue K, Wang C, Wang J et al (2021) A sensitive and reliable organic fluorescent nanothermometer for noninvasive temperature sensing. J Am Chem Soc 143:14147–14157. https://doi.org/10.1021/jacs.1c04597
Yang Y, Liu S, Zhang G et al (2023) Cellulose nanofiber encapsulated polyethylene glycol phase change composites containing AIE-gen for monitoring leak process. Compos - A: Appl Sci Manuf 107452. https://doi.org/10.1016/j.compositesa.2023.107452
Figueira-Duarte TM, Mullen K (2011) Pyrene-based materials for organic electronics. Chem Rev 111:7260–7314. https://doi.org/10.1021/cr100428a
Feng X, Hu JY, Redshaw C et al (2016) Functionalization of pyrene to prepare luminescent materials—typical examples of synthetic methodology. Chem–A Euro J 22:11898–11916. https://doi.org/10.1002/chem.201600465
Trattnig R, Pevzner L, Jäger M et al (2013) Bright blue solution processed triple-layer polymer light-emitting diodes realized by thermal layer stabilization and orthogonal solvents. Adv Func Mater 23:4897–4905. https://doi.org/10.1002/adfm.201300360
Ni XL, Zeng X, Redshaw C et al (2011) Ratiometric fluorescent receptors for both Zn2+ and H2PO4– ions based on a pyrenyl-linked triazole-modified homooxacalix[3]arene: a potential molecular traffic signal with an RS latch logic circuit. J Org Chem 76:5696–5702. https://doi.org/10.1021/jo2007303
Wang X, Wang L, Mao X et al (2021) Pyrene-based aggregation-induced emission luminogens (AIEgens) with less colour migration for anti-counterfeiting applications. J Mater Chem C 9:12828–12838. https://doi.org/10.1039/D1TC03022A
Liu Q, Yue S, Yan Z et al (2022) Cyano and isocyano-substituted tetraphenylethylene with AIE behavior and mechanoresponsive behavior. Chin J Struct Chem 41:2204075–2204082. https://doi.org/10.14102/j.cnki.0254-5861.2021-0049
Teo WE, Ramakrishna S (2006) A review on electrospinning design and nanofibre assemblies. Nanotechnology 17:R89. https://doi.org/10.1088/0957-4484/17/14/R01
Niu L, Li X, Zhang Y et al (2022) Electrospun lignin-based phase-change nanofiber films for solar energy storage. ACS Sustain Chem Eng 10:13081–13090. https://doi.org/10.1021/acssuschemeng.2c03462
Crawford AG, Liu Z, Mkhalid IA et al (2012) Synthesis of 2-and 2, 7-functionalized pyrene derivatives: an application of selective c h borylation. Chem–A Euro J 18:5022–5035. https://doi.org/10.1002/chem.201103774
Sreenivasulu C, Satyanarayana G (2018) Zinc-chloride-promoted domino reaction of phenols with terminal alkynes under solvent-free conditions: an efficient synthesis of chromenes. Eur J Org Chem 2018:2846–2857. https://doi.org/10.1002/ejoc.201800391
Crawford AG, Dwyer AD, Liu Z et al (2011) Experimental and theoretical studies of the photophysical properties of 2-and 2, 7-functionalized pyrene derivatives. J Am Chem Soc 133:13349–13362. https://doi.org/10.1021/ja2006862
McRae EG, Kasha M (1958) Enhancement of phosphorescence ability upon aggregation of dye molecules. J Chem Phys 28:721–722. https://doi.org/10.1063/1.1744225
Sasaki S, Suzuki S, Sameera W et al (2016) Highly twisted N, N-dialkylamines as a design strategy to tune simple aromatic hydrocarbons as steric environment-sensitive fluorophores. J Am Chem Soc 138:8194–8206. https://doi.org/10.1021/jacs.6b03749
Sasaki S, Suzuki S, Igawa K et al (2017) The K-region in pyrenes as a key position to activate aggregation-induced emission: effects of introducing highly twisted n, n-dimethylamines. J Org Chem 82:6865–6873. https://doi.org/10.1021/acs.joc.7b00996
Wang E, Lam J, Hu R et al (2014) Twisted intramolecular charge transfer, aggregation-induced emission, supramolecular self-assembly and the optical waveguide of barbituric acid-functionalized tetraphenylethene. J Mater Chem C 2:1801–1807. https://doi.org/10.1039/c3tc32161d
Kéri O, Bárdos P, Boyadjiev S et al (2019) Thermal properties of electrospun polyvinylpyrrolidone/titanium tetraisopropoxide composite nanofibers. J Therm Anal Calorim 137:1249–1254. https://doi.org/10.1007/s10973-019-08030-0
MacKenzie AP, Rasmussen DH (1972) Interactions in the water-polyvinylpyrrolidone system at low temperatures. In: Jellinek HHG (ed) Water structure at the water-polymer interface, Springer. https://doi.org/10.1007/978-1-4615-8681-4_12
Borrmann D, Danzer A, Sadowski G (2022) Water sorption in glassy polyvinylpyrrolidone-based polymers. Membranes 12:434. https://doi.org/10.3390/membranes12040434
Zhang J, Zhang H, Lam JW et al (2021) Restriction of intramolecular motion (RIM): investigating AIE mechanism from experimental and theoretical studies. Chem Res Chin Univ 37:1–15. https://doi.org/10.1007/s40242-021-0381-6
Wang P, Zhang W, Wang L et al (2021) Synthesis of superabsorbent polymer hydrogels with rapid swelling: effect of reaction medium dosage and polyvinylpyrrolidone on water absorption rate. Langmuir 37:14614–14621. https://doi.org/10.1021/acs.langmuir.1c02295
Zhang W, Wang P, Deng Y et al (2021) Preparation of superabsorbent polymer gel based on PVPP and its application in water-holding in sandy soil. J Environ Chemi Eng 9:106760. https://doi.org/10.1016/j.jece.2021.106760
Xu D, Huang Q, Yang L et al (2023) Experimental design of composite films with thermal management and electromagnetic shielding properties based on polyethylene glycol and MXene. Carbon 202:1–12. https://doi.org/10.1016/j.carbon.2022.11.010
Li W, Zhai D, Gu Y et al (2022) 3D zirconium phosphate/polyvinyl alcohol composite aerogels for form-stable phase change materials with brilliant thermal energy storage capability. Sol Energy Mater Sol Cells 239:111681. https://doi.org/10.1016/j.solmat.2022.111681
Weng M, Su J, Lin J et al (2023) Intrinsically lighting absorptive PANI/MXene aerogel encapsulated PEG to construct PCMs with efficient photothermal energy storage and stable reusability. Sol Energy Mater Sol Cells 254:112282. https://doi.org/10.1016/j.solmat.2023.112282
Wang J, He J, Ma L et al (2020) Multifunctional conductive cellulose fabric with flexibility, superamphiphobicity and flame-retardancy for all-weather wearable smart electronic textiles and high-temperature warning device. Chem Eng J 390:124508. https://doi.org/10.1016/j.cej.2020.124508
Fu T, Zhao X, Chen L et al (2019) Bioinspired color changing molecular sensor toward early fire detection based on transformation of phthalonitrile to phthalocyanine. Adv Func Mater 29:1806586. https://doi.org/10.1002/adfm.201806586
Qi Q, Liu Y, Fang X et al (2013) AIE (AIEE) and mechanofluorochromic performances of TPE-methoxylates: effects of single molecular conformations. RSC Adv 3:7996–8002. https://doi.org/10.1039/C3RA40734A
Liu S, Cheng Y, Li Y et al (2020) Manipulating solid-state intramolecular motion toward controlled fluorescence patterns. ACS Nano 14:2090–2098. https://doi.org/10.1021/acsnano.9b08761
Funding
This research was funded by the National Natural Science Foundation of China (grant nos. 52003111, 21975054, and U20A20340), National Key R&D Program of China (2020YFB0408100), the Program for Guangdong Introducing Innovative and Entrepreneurial Team (2016ZT06C412), and Foshan Science and Technology Innovation Team Project (1920001000108). CR thanks the University of Hull for support.
Author information
Authors and Affiliations
Contributions
Jintao Huang: methodology, writing—original draft, and conceptualization; Yiwei Liu: data curation and investigation; Jiahui Lin: validation and writing—original draft; Jingtao Su: software; Carl Redshaw: writing—review and editing; Xing Feng: supervision and funding acquisition; Yonggang Min: funding acquisition. Jintao Huang and Yiwei Liu contributed equally to this work.
Corresponding authors
Ethics declarations
Competing interests
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Jintao Huang and Yiwei Liu contributed equally to this work.
Supplementary Information
Below is the link to the electronic supplementary material.
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
Huang, J., Liu, Y., Lin, J. et al. Novel pyrene-based aggregation-induced emission luminogen (AIEgen) composite phase change fibers with satisfactory fluorescence anti-counterfeiting, temperature sensing, and high-temperature warning functions for solar-thermal energy storage. Adv Compos Hybrid Mater 6, 126 (2023). https://doi.org/10.1007/s42114-023-00706-4
Received:
Revised:
Accepted:
Published:
DOI: https://doi.org/10.1007/s42114-023-00706-4