New Insight on Photoisomerization Kinetics of Photo-Switchable Thin Films Based on Azobenzene/Graphene Hybrid Additives in Polyethylene Oxide
Abstract
:1. Introduction
2. Experimental Details
2.1. Materials
2.2. Synthesis of PEO-MR-Graphene Hybrid Composite Thin Films
2.3. Characterization
3. Results and Discussion
3.1. Characterization of PEO-(MR-Graphene) Hybrid Nanocomposite Thin Film
3.2. Kinetics of Photoisomerization Processes
3.3. Investigating the Photoisomerization Cycles
3.4. Atomic Force Microscope (AFM) Studies
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Data Availability
References
- Schneider, V.; Strunskus, T.; Elbahri, M.; Faupel, F.; Elbahri, M. Light-induced conductance switching in azobenzene based near-percolated single wall carbon nanotube/polymer composites. Carbon 2015, 90, 94–101. [Google Scholar] [CrossRef]
- Kim, M.; Safron, N.S.; Huang, C.; Arnold, M.S.; Gopalan, P. Light-Driven Reversible Modulation of Doping in Graphene. Nano Lett. 2012, 12, 182–187. [Google Scholar] [CrossRef]
- Pang, W.; Xue, J.; Pang, H. A High Energy Density Azobenzene/Graphene Oxide Hybrid with Weak Nonbonding Interactions for Solar Thermal Storage. Sci. Rep. 2019, 9, 5224. [Google Scholar] [CrossRef]
- Schuschke, C.; Hohner, C.; Jevric, M.; Petersen, A.U.; Wang, Z.; Schwarz, M.; Kettner, M.; Waidhas, F.; Fromm, L.; Sumby, C.J.; et al. Solar energy storage at an atomically defined organic-oxide hybrid interface. Nat. Commun. 2019, 10, 2384. [Google Scholar] [CrossRef] [Green Version]
- Mansø, M.; Petersen, A.U.; Wang, Z.; Erhart, P.; Nielsen, M.B.; Moth-Poulsen, K. Molecular solar thermal energy storage in photoswitch oligomers increases energy densities and storage times. Nat. Commun. 2018, 9, 1945. [Google Scholar] [CrossRef]
- Wang, Z.; Udmark, J.; Börjesson, K.; Rodrigues, R.; Roffey, A.; Abrahamsson, M.; Nielsen, M.B.; Moth-Poulsen, K. Evaluating Dihydroazulene/Vinylheptafulvene Photoswitches for Solar Energy Storage Applications. ChemSusChem 2017, 10, 3049–3055. [Google Scholar] [CrossRef] [PubMed]
- Alsaad, A.; Al-Bataineh, Q.M.; Telfah, M.; Ahmad, A.A.; AlBataineh, Z.; Telfah, A. Optical properties and photo-isomerization processes of PMMA–BDK–MR nanocomposite thin films doped by silica nanoparticles. Polym. Bull. 2020, 1–17. [Google Scholar] [CrossRef]
- Blinov, L.M.; Kawai, T.; Kozlovsky, M.V.; Kawata, Y.; Ichimura, K.; Seki, T.; Tripathy, S.; Li, L.; Oliveira, O., Jr.; Irie, M. Photoreactive Organic Thin Films; Elsevier: Amsterdam, The Netherlands, 2002. [Google Scholar]
- AlBataineh, Z.; Ahmad, A.A.; Alsaad, A.; Qattan, I.A.; Bani-Salameh, A.A.; Telfah, A. Kinematics of Photoisomerization Processes of PMMA-BDK-MR Polymer Composite Thin Films. Polymers 2020, 12, 1275. [Google Scholar] [CrossRef]
- Ahmad, A.A.; Alsaad, A.M.; Al-Bataineh, Q.M.; Al-Akhras, M.-A.H.; AlBataineh, Z.; Alizzy, K.A.; Daoud, N.S. Synthesis and characterization of ZnO NPs-doped PMMA-BDK-MR polymer-coated thin films with UV curing for optical data storage applications. Polym. Bull. 2020, 1–23. [Google Scholar] [CrossRef]
- Morgenstern, K. Isomerization reactions on single adsorbed molecules. Acc. Chem. Res. 2009, 42, 213–223. [Google Scholar] [CrossRef]
- Henzl, J.; Mehlhorn, M.; Gawronski, H.; Rieder, K.H.; Morgenstern, K. Reversible cis–trans isomerization of a single azobenzene molecule. Angew. Chem. Int. Ed. 2006, 45, 603–606. [Google Scholar] [CrossRef] [PubMed]
- Choi, B.-Y.; Kahng, S.-J.; Kim, S.; Kim, H.; Kim, H.W.; Song, Y.J.; Ihm, J.; Kuk, Y. Conformational Molecular Switch of the Azobenzene Molecule: A Scanning Tunneling Microscopy Study. Phys. Rev. Lett. 2006, 96, 156106. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Georgiou, D.; Melidis, P.; Aivasidis, A.; Gimouhopoulos, K. Degradation of azo-reactive dyes by ultraviolet radiation in the presence of hydrogen peroxide. Dye. Pigment. 2002, 52, 69–78. [Google Scholar] [CrossRef]
- Ashter, S.A. Introduction to Bioplastics Engineering; Elsevier: Amsterdam, The Netherlands, 2016. [Google Scholar]
- Ashter, S.A. 7-processing biodegradable polymers. In Introduction to Bioplastics Engineering; William Andrew Publishing: Oxford, UK, 2016; pp. 179–209. [Google Scholar]
- Izdebska, J. Aging and Degradation of Printed Materials. Print. Polym. 2016, 353–370. [Google Scholar] [CrossRef]
- Ebrahimi, H.R.; Modrek, M. Photocatalytic Decomposition of Methyl Red Dye by Using Nanosized Zinc Oxide Deposited on Glass Beads in Various pH and Various Atmosphere. J. Chem. 2013, 2013, 151034. [Google Scholar] [CrossRef] [Green Version]
- Yaqoob, A.A.; Serrà, A.; Ibrahim, M.N.M. Advances and Challenges in Developing Efficient Graphene Oxide-Based ZnO Photocatalysts for Dye Photo-Oxidation. Nanomaterials 2020, 10, 932. [Google Scholar] [CrossRef]
- Zrnčić, M.; Ljubas, D.; Ćurković, L.; Škorić, I.; Babić, S. Kinetics and degradation pathways of photolytic and photocatalytic oxidation of the anthelmintic drug praziquantel. J. Hazard. Mater. 2017, 323, 500–512. [Google Scholar]
- Anwer, H.; Mahmood, A.; Lee, J.; Kim, K.-H.; Park, J.-W.; Yip, A.C.K. Photocatalysts for degradation of dyes in industrial effluents: Opportunities and challenges. Nano Res. 2019, 12, 955–972. [Google Scholar] [CrossRef]
- Shi, Y.; Steier, W.H.; Yu, L.; Chen, M.; Dalton, L.R. Large stable photoinduced refractive index change in a nonlinear optical polyester polymer with disperse red side groups. Appl. Phys. Lett. 1991, 58, 1131–1133. [Google Scholar] [CrossRef]
- Sekkat, Z.; Morichère, D.; Dumont, M.; Loucif-Saïbi, R.; Delaire, J.A. Photoisomerization of azobenzene derivatives in polymeric thin films. J. Appl. Phys. 1992, 71, 1543–1545. [Google Scholar] [CrossRef]
- Zhang, X.; Feng, Y.; Huang, D.; Li, Y.; Feng, W. Investigation of optical modulated conductance effects based on a graphene oxide–azobenzene hybrid. Carbon 2010, 48, 3236–3241. [Google Scholar] [CrossRef]
- Coelho, P.J.; Sousa, C.M.; Castro, M.C.R.; Fonseca, A.M.C.; Raposo, M.M.M. Fast thermal cis–trans isomerization of heterocyclic azo dyes in PMMA polymers. Opt. Mater. 2013, 35, 1167–1172. [Google Scholar] [CrossRef] [Green Version]
- Feringa, B.; Jager, W.F.; De Lange, B. Organic materials for reversible optical data storage. Tetrahedron 1993, 49, 8267–8310. [Google Scholar] [CrossRef]
- Karmakar, A.; Ghosh, A. Charge carrier dynamics and relaxation in (polyethylene oxide-lithium-salt)-based polymer electrolyte containing 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide as ionic liquid. Phys. Rev. E 2011, 84, 051802. [Google Scholar] [CrossRef] [PubMed]
- Morsi, M.; Rajeh, A.; Al-Muntaser, A. Reinforcement of the optical, thermal and electrical properties of PEO based on MWCNTs/Au hybrid fillers: Nanodielectric materials for organoelectronic devices. Compos. Part B Eng. 2019, 173, 106957. [Google Scholar] [CrossRef]
- Abutalib, M.; Rajeh, A. Influence of ZnO/Ag nanoparticles doping on the structural, thermal, optical and electrical properties of PAM/PEO composite. Phys. B Condens. Matter 2020, 578, 411796. [Google Scholar] [CrossRef]
- Hadi, A.; Hashim, A.; Al-Khafaji, Y. Structural, Optical and Electrical Properties of PVA/PEO/SnO2 New Nanocomposites for Flexible Devices. Trans. Electr. Electron. Mater. 2020, 21, 283–292. [Google Scholar] [CrossRef]
- Li, Y.; Chen, Z. XH/π (X = C, Si) interactions in graphene and silicene: Weak in strength, strong in tuning band structures. J. Phys. Chem. Lett. 2013, 4, 269–275. [Google Scholar] [CrossRef]
- Dutta, P.; Nandi, D.; Datta, S.; Chakraborty, S.; Das, N.; Chatterjee, S.; Ghosh, U.C.; Halder, A. Excitation wavelength dependent UV fluorescence of dispersed modified graphene oxide: Effect of pH. J. Lumin. 2015, 168, 269–275. [Google Scholar] [CrossRef]
- Wang, D.; Ye, G.; Wang, X.; Wang, X. Graphene Functionalized with Azo Polymer Brushes: Surface-Initiated Polymerization and Photoresponsive Properties. Adv. Mater. 2011, 23, 1122–1125. [Google Scholar] [CrossRef]
- Saladaga, I.A.; Janthasit, S.; de Luna, M.D.G.; Grisdanurak, N.; Tantrawong, S.; Paoprasert, P. Poly (oligoethylene Glycol Methacrylate): A Promising Electrolyte Polymer. Chiang Mai J. Sci. 2015, 42, 868–876. [Google Scholar]
- Saeed, K.; Ishaq, M.; Ilyas, M. Preparation, morphology, and thermomechanical properties of coal ash/polyethylene oxide composites. Turk. J. Chem. 2011, 35, 237–243. [Google Scholar]
- Kucharski, T.J.; Tian, Y.; Akbulatov, S.; Boulatov, R. Chemical solutions for the closed-cycle storage of solar energy. Energy Environ. Sci. 2011, 4, 4449. [Google Scholar] [CrossRef]
- Feng, Y.; Liu, H.; Luo, W.; Liu, E.; Zhao, N.; Yoshino, K.; Feng, W. Covalent functionalization of graphene by azobenzene with molecular hydrogen bonds for long-term solar thermal storage. Sci. Rep. 2013, 3, 3260. [Google Scholar] [CrossRef]
- Shin, K.-H.; Shin, E.J. Photoresponsive Azobenzene-modified Gold Nanoparticle. Bull. Korean Chem. Soc. 2008, 29, 1259–1262. [Google Scholar]
- Yang, Y.; Hughes, R.P.; Aprahamian, I. Visible Light Switching of a BF2-Coordinated Azo Compound. J. Am. Chem. Soc. 2012, 134, 15221–15224. [Google Scholar] [CrossRef]
- Reichardt, C. Solvatochromic Dyes as Solvent Polarity Indicators. Chem. Rev. 1994, 94, 2319–2358. [Google Scholar] [CrossRef]
- Ozen, A.S.; Doruker, P.; Aviyente, V. Effect of Cooperative Hydrogen Bonding in Azo−Hydrazone Tautomerism of Azo Dyes. J. Phys. Chem. A 2007, 111, 13506–13514. [Google Scholar] [CrossRef]
- Ruzza, P.; Hussain, R.; Biondi, B.; Calderan, A.; Tessari, I.; Bubacco, L.; Siligardi, G. Effects of Trehalose on Thermodynamic Properties of Alpha-synuclein Revealed through Synchrotron Radiation Circular Dichroism. Biomolecules 2015, 5, 724–734. [Google Scholar] [CrossRef] [Green Version]
- Lee, G.J.; Kim, N.; Lee, M. Photophysical properties and photoisomerization processes of Methyl Red embedded in rigid polymer. Appl. Opt. 1995, 34, 138–143. [Google Scholar] [CrossRef]
- Airinei, A.; Buruiana, E.C. Photoisomerization of AZO Aromatic Chromophobes in Polyvinyl Chloride. J. Macromol. Sci. Part A 1994, 31, 1233–1239. [Google Scholar] [CrossRef]
AZO–Graphene | 3.822 × 10−3 | 3.022 | 2.012 | 1.634 × 10−4 | 70.692 | 2.093 |
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Al-Bataineh, Q.M.; Ahmad, A.A.; Alsaad, A.M.; Telfah, A. New Insight on Photoisomerization Kinetics of Photo-Switchable Thin Films Based on Azobenzene/Graphene Hybrid Additives in Polyethylene Oxide. Polymers 2020, 12, 2954. https://doi.org/10.3390/polym12122954
Al-Bataineh QM, Ahmad AA, Alsaad AM, Telfah A. New Insight on Photoisomerization Kinetics of Photo-Switchable Thin Films Based on Azobenzene/Graphene Hybrid Additives in Polyethylene Oxide. Polymers. 2020; 12(12):2954. https://doi.org/10.3390/polym12122954
Chicago/Turabian StyleAl-Bataineh, Qais M., Ahmad A. Ahmad, Ahmad M. Alsaad, and Ahmad Telfah. 2020. "New Insight on Photoisomerization Kinetics of Photo-Switchable Thin Films Based on Azobenzene/Graphene Hybrid Additives in Polyethylene Oxide" Polymers 12, no. 12: 2954. https://doi.org/10.3390/polym12122954