Design, Synthesis, and Potential Applications of a Novel Hydrophilic Fluorinated Monomer

Authors

  • Lin Huang
  • Yiwen Ren
  • Junjie Wang
  • Wenhui Chen
  • Wenjie Yu
  • Xiaoyan Ma
  • Xianrong Cai

DOI:

https://doi.org/10.6911/WSRJ.202408_10(8).0007

Keywords:

Catechol; Trifluorochloroethylene; Synthesis; Hydrophilicity; Fluorinated monomer.

Abstract

Catechol and trifluorochloroethylene are two compounds with unique properties and advantages in applications. In this study, a novel hydrophilic fluorinated monomer was successfully synthesized by coupling a catechol derivative and trifluorochloroethylene, and the structure of the monomer was characterized. From the perspective of the monomer structure, it shows potential applications as pharmaceutical intermediates and biomedical polymers in hydrophilic drug design and biomedical materials. This article aims to explore the synthesis process, chemical structure, and possible application pathways of this new monomer.

Downloads

Download data is not yet available.

References

J. L. Rodriguez, S. Z. Trooskin, R. S. Greco, et al. Reduced bacterial adherence to surfactant-coated catheters, Current Surgery, vol. 43 (1986), 423-425.

S. Jo, K. Park. Surface modification using silanated poly (ethylene glycol) s, Biomaterials, vol. 21 (2000), 605-616.

J. Saiz-Poseu, J. Faraudo, A Figueras, et al. Switchable Self-Assembly of a Bioinspired Alkyl Catechol at a Solid/Liquid Interface: Competitive Interfacial, Noncovalent, and Solvent Interactions, Chemistry-A European Journal, vol, 18 (2012), 3056-3063.

L. Wang, D. Wang, Z. Dong, et al. Interface chemistry engineering for stable cycling of reduced GO/SnO2 nanocomposites for lithiumion battery, Nano Letters, vol 13 (2013), 1711-171.

M. Krogsgaard, A.M. Behrens, J.S Pedersen, et al. Self-Healing Mussel-Inspired Multi-pH-Responsive Hydrogels, Biomacromolecules, vol. 14 (2013), 297-301.

J. Sedó, J. Saiz-Poseu, F. Busqué, et al. Catechol-Based Biomimetic Functional Materials, Advanced Materials, vol. 25(2013), 653-701.

H. Fan, J.P. Gong. Bioinspired Underwater Adhesives, Advanced Materials, vol. 33 (2021), 2102983.

J.J. Wilker. Biomaterials: Redox and adhesion on the rocks, Nature Chemical Biology, vol. 7 (2011), 579-580.

N. Patil, C. Jérôme, C. Detrembleur. Recent Advances in the Synthesis of Catechol-Derived (Bio)Polymers for Applications in Energy Storage and Environment, Progress in Polymer Science, vol. 82 (2018), 34-91.

Q. Ye, F. Zhou, W. Liu. Bioinspired catecholic chemistry for surface modification, Chemical Society Reviews, vol. 40 (2011), 4244-4258.

H. Meng, P.K. Forooshani, P.U. Joshi, et al. Biomimetic recyclable microgels for on-demand generation of hydrogen peroxide and antipathogenic application, Acta Biomaterialia, vol. 83 (2019), 109-118.

P. Kord Forooshani, E. Polega, K. Thomson, et al. Antibacterial Properties of Mussel-Inspired Polydopamine Coatings Prepared by a Simple Two-Step Shaking-Assisted Method, Frontiers in Chemistry, vol. 7 (2019), 631.

W. Zhang, R. Wang, Z.M. Sun, et al. Catechol-functionalized hydrogels: biomimetic design, adhesion mechanism, and biomedical applications, Chemical Society Reviews, vol. 49 (2020), 433-464.

B. Liu, C. Zhou, Z. Zhang, et al. Antimicrobial Property of Halogenated Catechols, Chemical Engineering Journal, vol. 403 (2021), 126340.

H. Lee, B.P. Lee, P.B. Messersmith. A reversible wet/dry adhesive inspired by mussels and geckos, Nature, vol. 448 (2007), 338-341.

H. Lee, K.D. Lee, K.B. Pyo, et al. Catechol-Grafted Poly(ethylene glycol) for PEGylation on Versatile Substrates, Langmuir, vol. 26 (2010), 3790-3793.

J. Lv, Y. Cheng. Fluoropolymers in biomedical applications: state-of-the-art and future perspectives, Chemical Society Reviews, vol. 50 (2021), 5435-5467.

A. Vitale, R. Bongiovanni, B. Ameduri. Fluorinated Oligomers and Polymers in Photopolymerization, Chemical Reviews, vol. 115 (2015), 8835-8866.

Y. Cao, H.Wu, S.I. Allec, et al. A Highly Stretchy, Transparent Elastomer with the Capability to Automatically Self-Heal Underwater, Advanced Materials, vol. 30 (2018), 1804602.

A.J. Dias, T.J. McCarthy. Introduction of carboxylic acid, aldehyde, and alcohol functional groups onto the surface of poly(chlorotrifluoroethylene), Macromolecules, vol. 20 (1987), 2068-2076.

M.S. Shoichet, T.J. McCarthy. Convenient syntheses of carboxylic acid functionalized fluoropolymer surfaces, Macromolecules, vol. 24 (1991), 98-986.

T.G. Bee, T.J. McCarthy. Surface modification of poly(chlorotrifluoroethylene): introduction of reactive carboxylic acid functionality, Macromolecules, vol. 25 (1992), 2093-2098.

N.D. Danielson, R.T. Taylor, J.A. Huth. Reactivity of Kel-F polymers with organolithium and organomagnesium compounds, Industrial & Engineering Chemistry Product Research and Development, vol. 22 (1983), 303-307.

R.W. Siergiej, N.D. Danielson. Phenyl-modified Kel-F as a column packing for liquid chromatography, Analytical Chemistry, vol. 55 (1983), 17-22.

L.G. Beaver, N.D. Danielson. Reactivity of poly(chlorotrifluoroethylene) (PCTFE) oil and PCTFE derivatives with phenyllithium and phenyl Grignard reagents, Polymer Bulletin, vol. 30 (1993), 47-54.

M. Kruempelman, N.D. Danielson. Liquid chromatographic characterization of picolyl Kel-F as a reverse-phase, weak anion-exchange column packing, Analytical Chemistry, vol. 57 (1985), 340-346.

R.T. Taylor, M.W. Pelter. The reaction of chlorofluoropolymers with sulfur nucleophiles, Journal of Polymer Science Part C: Polymer Letters, vol. 25 (1987), 215-217.

T. Yamamoto, T. Yamakawa. Pd-Catalyzed Arylation of Chlorotrifluoroethylene Using Arylboronic Acids, Organic Letters, vol. 14 (2012), 3454-3457.

T. Imae. Fluorinated polymers, Current Opinion in Colloid & Interface Science, vol. 8 (2003), 307-314.

E. Leivo, T. Wilenius, T. Kinos, et al. Properties of thermally sprayed fluoropolymer PVDF, ECTFE, PFA and FEP coatings, Progress in Organic Coatings, vol. 49 (2004), 69-73.

X. Yao, S.S. Dunn, P. Kim. Fluorogel Elastomers with Tunable Transparency, Elasticity, Shape-Memory, and Antifouling Properties, Angewandte Chemie International Edition, vol. 53 (2014), 4418-4422.

Y.S. Lee, G. Collins, T.L. Arinzeh. Neurite extension of primary neurons on electrospun piezoelectric scaffolds, Acta Biomaterialia, vol. 7 (2016), 3877-3886.

V.F. Cardoso, D.M. Correia, C. Ribeiro, et al. Fluorinated Polymers as Smart Materials for Advanced Biomedical Applications, Polymers, vol. 10 (2015), 161.

F. Boschet, B. Ameduri. (Co)polymers of Chlorotrifluoroethylene: Synthesis, Properties, and Applications, Chemical Reviews, vol. 114 (2011), 927-980.

S.H. Ku, J. Ryu, S.K. Hong, et al. General functionalization route for cell adhesion on non-wetting surfaces, Biomaterials, vol. 31 (2018), 2535-2541.

A.C. Cave, A.C. Brewer., A Narayanapanicker., et al. NADPH Oxidases in Cardiovascular Health and Disease, Antioxidants & Redox Signaling, vol. 8(2014), 691-728.

H. Watanabe, A. Fujimoto, J. Nishida, et al. Bio-based Polymer Coating Using Catechol Derivative Urushiol, Langmuir, vol. 32 (2010), 4619-4623.

P.S. Yavvari, A. Srivastava. Robust, self-healing hydrogels synthesised from catechol rich polymers, Journal of Materials Chemistry B, vol. 3 (2006), 899-910.

Downloads

Published

2024-07-24

Issue

Section

Articles

How to Cite

Huang, Lin, Yiwen Ren, Junjie Wang, Wenhui Chen, Wenjie Yu, Xiaoyan Ma, and Xianrong Cai. 2024. “Design, Synthesis, and Potential Applications of a Novel Hydrophilic Fluorinated Monomer”. World Scientific Research Journal 10 (8): 44-58. https://doi.org/10.6911/WSRJ.202408_10(8).0007.