Abstract
Tetrafluoro-λ6-sulfanyl (–SF4–) was synthesized via oxidative fluorination and used as a bridging group to bond perfluoroalkyl to phenylene. As a result, perfluoroalkylphenyltrichlorosilane was prepared by hydrosilylation using perfluoroalkylstyrene as a raw material under platinum catalytic conditions. And the corresponding monolayers produced a coating on silicon surfaces by spontaneous self-assembly from solution. Due to the introduction of –SF4–, it can increase the shielding effect of the fluoroalkyl group and reduce the surface energy of the material on the basis of extending the length of the perfluoroalkyl chain. At the same time, the sulfur–carbon bond formed by the bridge group is more likely to decrease under ultraviolet light. Once the bridge bond is broken, the perfluoroalkyl-terminated carbon chain perfluoroalkyl group is decomposed and detached. Therefore, the fluorine-containing material has good ultraviolet light degradation property, and the obtained fluorine-containing material is environmentally friendly. The self-assembled film containing a perfluoroalkylsilane can effectively reduce the friction properties and adhesion of the substrate, and the substrate modified with the self-assembled film containing a perfluoroalkylsilane has good stability.
Similar content being viewed by others
References
Biegel LB, Hurtt ME, Frame SR, O’Connor JC, Cook JC (2001) Mechanisms of extrahepatic tumor induction by peroxisome proliferators in male CD rats. Toxicol Sci 60(1):44–55. https://doi.org/10.1093/toxsci/60.1.44
Brendel S, Fetter É, Staude C, Vierke L, Biegel-Engler A (2018) Short-chain perfluoroalkyl acids: environmental concerns and a regulatory strategy under REACH. Environ Sci Europe 30(1):9. https://doi.org/10.1186/s12302-018-0134-4
Buck RC, Franklin J, Berger U, Conder JM, Cousins IT, De Voogt P, van Leeuwen SP (2011) Perfluoroalkyl and polyfluoroalkyl substances in the environment: terminology, classification, and origins. Integr Environ Assess Manag 7(4):513–541. https://doi.org/10.1002/ieam.258
Cai L, Li Z (2015) Preparation of fluoroalkylsilyl polymethacrylates and their waterproof application on cotton fabrics. Fibers Polymers 16(10):2094–2105. https://doi.org/10.1007/s12221-015-5505-5
DePalma V, Tillman N (1989) Friction and wear of self-assembled trichlorosilane monolayer films on silicon. Langmuir 5(3):868–872. https://doi.org/10.1021/la00087a049
Ellis DA, Martin JW, De Silva AO, Mabury SA, Hurley MD, Sulbaek Andersen MP, Wallington TJ (2004) Degradation of fluorotelomer alcohols: a likely atmospheric source of perfluorinated carboxylic acids. Environ Sci Technol 38(12):3316–3321. https://doi.org/10.1021/es049860w
Guo J, Resnick P, Efimenko K, Genzer J, DeSimone JM (2008) Alternative fluoropolymers to avoid the challenges associated with perfluorooctanoic acid. Ind Eng Chem Res 47(3):502–508. https://doi.org/10.1021/ie0703179
Honda K, Morita M, Otsuka H, Takahara A (2005) Molecular aggregation structure and surface properties of poly (fluoroalkyl acrylate) thin films. Macromolecules 38(13):5699–5705. https://doi.org/10.1021/ma050394k
Huang JQ, Meng WD, Qing FL (2007) Synthesis and repellent properties of vinylidene fluoride-containing polyacrylates. J Fluor Chem 128(12):1469–1477. https://doi.org/10.1016/j.jfluchem.2007.08.005
Kannan K, Koistinen J, Beckmen K, Evans T, Gorzelany JF, Hansen KJ, Giesy JP (2001) Accumulation of perfluorooctane sulfonate in marine mammals. Environ Sci Technol 35(8):1593–1598. https://doi.org/10.1021/es001873w
Kudo N, Kawashima Y (2003) Toxicity and toxicokinetics of perfluorooctanoic acid in humans and animals. J Toxicol Sci 28(2):49–57. https://doi.org/10.2131/jts.28.49
Lee MT, Hsueh CC, Freund MS, Ferguson GS (1998) Air oxidation of self-assembled monolayers on polycrystalline gold: the role of the gold substrate. Langmuir 14(22):6419–6423. https://doi.org/10.1021/la980724c
Lee YC, Lo SL, Chiueh PT, Chang DG (2009) Efficient decomposition of perfluorocarboxylic acids in aqueous solution using microwave-induced persulfate. Water Res 43(11):2811–2816. https://doi.org/10.1016/j.watres.2009.03.052
Li L, Zheng H, Wang T, Cai M, Wang P (2018) Perfluoroalkyl acids in surface seawater from the North Pacific to the Arctic Ocean: contamination, distribution and transportation. Environ Pollut 238:168–176. https://doi.org/10.1016/j.envpol.2018.03.018
Martin JW, Smithwick MM, Braune BM, Hoekstra PF, Muir DC, Mabury SA (2004) Identification of long-chain perfluorinated acids in biota from the Canadian Arctic. Environ Sci Technol 38(2):373–380. https://doi.org/10.1021/es034727+
Nixon PG, Winter R, Castner DG, Holcomb NR, Grainger DW, Gard GL (2000) Pentafluoro-λ6-sulfanyl-terminated chlorosilanes: new SF5-Containing films and polysiloxane materials. Chem Mater 12(10):3108–3112. https://doi.org/10.1021/cm000339k
Petrovykh DY, Kimura-Suda H, Opdahl A, Richter LJ, Tarlov MJ, Whitman LJ (2006) Alkanethiols on platinum: multicomponent self-assembled monolayers. Langmuir 22(6):2578–2587. https://doi.org/10.1021/la050928a
Saidi S, Guittard F, Guimon C, Géribaldi S (2005) Fluorinated comblike homopolymers: the effect of spacer lengths on surface properties. J Polym Sci, Part A: Polym Chem 43(17):3737–3747. https://doi.org/10.1002/pola.20851
Sohlenius AK, Eriksson AM, Högström C, Kimland M, DePierre JW (2010) Perfluorooctane sulfonic acid is a potent inducer of peroxisomal fatty acid β-oxidation and other activities known to be affected by peroxisome proliferators in mouse liver. Pharmacol Toxicol 72(2):90–93. https://doi.org/10.1111/j.1600-0773.1993.tb00296.x
Upham BL, Deocampo ND, Wurl B, Trosko JE (1998) Inhibition of gap junctional intercellular communication by perfluorinated fatty acids is dependent on the chain length of the fluorinated tail. Int J Cancer 78(4):491–495. https://doi.org/10.1002/(SICI)1097-0215(19981109)78:4%3C491:AID-IJC16%3E3.0.CO;2-9
Wang Q, Zhang Q, Zhan X, Chen F (2010) Structure and surface properties of polyacrylates with short fluorocarbon side chain: role of the main chain and spacer group. J Polym Sci, Part A: Polym Chem 48(12):2584–2593. https://doi.org/10.1002/pola.24038
Wang XT, Chen L, Li ZX (2019) Perfluoroalkylstyrene and application thereof, CN 110294699 A
Wen W, Xia X, Hu D, Zhou D, Wang H, Zhai Y, Lin H (2017) Long-chain perfluoroalkyl acids (PFAAs) affect the bioconcentration and tissue distribution of short-chain PFAAs in zebrafish (Danio rerio). Environ Sci Technol 51(21):12358–12368. https://doi.org/10.1021/acs.est.7b03647
Willey TM, Vance AL, Van Buuren T, Bostedt C, Terminello LJ, Fadley CS (2005) Rapid degradation of alkanethiol-based self-assembled monolayers on gold in ambient laboratory conditions. Surf Sci 576(1–3):188–196. https://doi.org/10.1016/j.susc.2004.12.022
Winter R, Nixon PG, Gard GL, Castner DG, Holcomb NR, Hu YH, Grainger DW (1999) Photopolymerized acrylate copolymer films with surfaces enriched in sulfur pentafluoride (−SF5) chemistry. Chem Mater 11(11):3044–3049. https://doi.org/10.1021/cm981102f
Winter R, Nixon PG, Gard GL, Graham DJ, Castner DG, Holcomb NR, Grainger DW (2004) Self-assembled organic monolayers terminated in perfluoroalkyl pentafluoro-λ6-sulfanyl (-SF5) chemistry on gold. Langmuir 20(14):5776–5781. https://doi.org/10.1021/la040011w
Wu L, Cai L, Liu A, Wang W, Yuan Y, Li Z (2015) Self-assembled monolayers of perfluoroalkylsilane on plasma-hydroxylated silicon substrates. Appl Surf Sci 349:683–694. https://doi.org/10.1016/j.apsusc.2015.05.073
Wu Y, Chen L, Li P (2019) Perfluoroalkyltetrafluorothiomethylene styrene copolymer and application thereof, CN 110256623 A
Yang W, Chen Y, Han D, Zhu L (2013) Synthesis and characterization of the fluorinated acrylic latex: effect of fluorine-containing surfactant on properties of the latex film. J Fluor Chem 149:8–12. https://doi.org/10.1016/j.jfluchem.2013.02.005
Ye T, McArthur EA, Borguet E (2005) Mechanism of UV photoreactivity of alkylsiloxane self-assembled monolayers. J Phys Chem B 109(20):9927–9938. https://doi.org/10.1021/jp0474273
Yoshino N, Sasaki A, Seto T (1995) Synthesis of a silane coupling agent containing a 4-(perfluoroalkyl)phenyl group and its application to the surface modification of glass. J Fluor Chem 71(1):21–29. https://doi.org/10.1016/0022-1139(94)03165-V
Zang X, Cai L, Li Z (2016) Fluoroalkylation of poly (cyclopentadienyl) siloxane and the surface properties of poly (fluorocyclopentenyl) siloxane films. Phosphorus Sulfur Silicon Related Elements 191(9):1204–1208. https://doi.org/10.1080/10426507.2014.996645
Zhou Z, Liang Y, Shi Y, Xu L, Cai Y (2013) Occurrence and transport of perfluoroalkyl acids (PFAAs), including short-chain PFAAs in Tangxun Lake, China. Environ Sci Technol 47(16):9249–9257. https://doi.org/10.1021/es402120y
Acknowledgements
We would like to express our sincere gratitude to the support of the National Natural Science Foundation of China (51673137) and the priority academic program development project of higher education institutions in Jiangsu Province.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wang, F., Chen, L., Xu, D. et al. UV-degradable perfluoroalkyl bridged bonding with tetrafluoro-λ6-sulfanyl. Chem. Pap. 74, 4125–4133 (2020). https://doi.org/10.1007/s11696-020-01233-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-020-01233-y