Abstract
Novel monomers based on (2Z)-2-(benzylidene)-6-hydroxy-1-benzofuran-3 (2H)-one with different substituents were synthesized by reaction of acylation with methacryloyl chloride. Kinetic of homopolymerization was investigated by dylatometric method. The synthesis of copolymers based on novel aurone containing monomers and methylmethacrylate was conducted in 10% dimethylformamide solution with 2,2ˊ-azobisisobutyronitrile as radical initiator at 80 °C (argon atmosphere). All structures of novel monomers were identified by 1H NMR and MS. The photochemical properties of synthesized aurone containing polymers have been investigated by UV VIS spectroscopy. It was found that aurone moiety in the side chain of polymer has been shown ability to Z-E-isomerization under irradiation with wavelength 365 nm. The half-reaction periods for Z-isomers of aurone containing polymers were calculated.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Celest S, Thierry V, Andre P (2000) Second-order non-linear optical polymers. Macromol Rapid Comm 21(1):1. https://doi.org/10.1002/(SICI)1521-3927(20000101)21:1%3c1::AID-MARC1%3e3.0.CO;2-X
Prasad PN et al (1991) Introduction to nonlinear optical effects in molecules and polymers. Wiley, New York
Che P, He Y, Wang X (2005) Hyperbranched Azo-polymers synthesized by Azo-coupling reaction of an AB2 monomer and postpolymerization modification. Macromolecules 38(21):8657. https://doi.org/10.1021/ma0511393
Derouiche Y, Koynov K et al (2012) Optical, electro-optical, and dielectric properties of acrylic tripropyleneglycol based polymer network systems including LCs. Mol Cryst Liq Cryst 561(1):124–135. https://doi.org/10.1080/15421406.2012.687149
Palessonga D, et al (2015). Tuning of microwave and optical properties of the electro-optic polymer PMMA-DR1 by loading with SiC nanoparticles for optimization of photonic microwave components. In: 23rd Telecommunications Forum Telfor (TELFOR), Belgrade, pp. 532–535. https://doi.org/10.1109/TELFOR.2015.7377523
Najjar R, Bigdeli E (2018) Synthesis of novel core-shells of PMMA with coumarin based liquid crystalline side chains and PMMA shell as electro-optical materials. Eur Polymer J 104:36–146. https://doi.org/10.1016/j.eurpolymj.2018.05.012
Kent ME, Rapp RP, Smith KM (2006) Antibiotic beads and osteomyelitis: here today, what’s coming tomorrow. Orthopedics 29(7):599–603. https://doi.org/10.3928/01477447-20060701-02
Wentao Z, Lei G, Liu Y, Wang W, Song T, Fan J (2017) Approach to osteomyelitis treatment with antibiotic loaded PMMA. Microb Pathog 102:42–44. https://doi.org/10.1016/j.micpath.2016.11.016
Soper SA, et al (2002) Contact conductivity detection in poly (methyl methacylate)-based microfluidic devices for analysis of mono-and polyanionic molecules. Anal Chem 74(10):2407–2415. https://doi.org/10.1021/ac011058e
Boone TD, et al (2002) The devices debuted in silicon and glass, but plastic fabrication may make them hugely successful in biotechnology applications. Anal Chem 74(3):78 A–86 A. https://doi.org/10.1021/ac021943c
Becker H, Locascio LE (2002) Polymer microfluidic devices. Talanta 56:267–287. https://doi.org/10.1016/s0039-9140(01)00594-x
Espinosa-Bustos C et al (2017) Fluorescence properties of aurone derivatives: an experimental and theoretical study with some preliminary biological applications. Photochem Photobiol Sci 16:1268–1276. https://doi.org/10.1039/C7PP00078B
Smokal V, Kharchenko O, Karabets Y, Iukhymenko N, Kysil A, Krupka O, Kolendo A (2018) Photochemical activities of polymers with aurone fragment. Mol Cryst Liq Cryst 672(1):11–17. https://doi.org/10.1080/15421406.2018.1542102
Zwick V et al (2014) Aurones as histone deacetylase inhibitors: Identification of key features. Bioorg Med Chem Lett 24:5497–5501. https://doi.org/10.1016/j.bmcl.2014.10.019
Detsi A et al (2009) Natural and synthetic 2’-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. Bioorg Med Chem 17:8073–8085. https://doi.org/10.1016/j.bmc.2009.10.002
Hadjeri M, Beney C, Boumendjel A (2003) Recent advances in the synthesis of conveniently substituted flavones, quinolones, chalcones and aurones: Potential biologically active molecules. Curr Org Chem 7(7):679–689. https://doi.org/10.2174/1385272033486765
Bhasker N, Reddy MK (2011) Synthesis and antibacterial activity of prenyloxy chalcones and prenyloxy aurones, Indian. J Heterocy Ch 21:49–52
Kim JM et al (2013) Suppression of TPA-induced tumor cell invasion by sulfuretin via inhibition of NF-kappaB-dependent MMP-9 expression. Oncol Rep 29:1231–1237. https://doi.org/10.3892/or.2012.2218
Kumar KS, Kumaresan R (2011) A quantum chemical study on the antioxidant properties of Aureusidin and Bracteatin. Int J Quantum Chem 111:4483–4496. https://doi.org/10.1002/qua.22964
Siddaiah V et al (2007) Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata. Bioorg Med Chem Lett 17:1288–1290. https://doi.org/10.1016/j.bmcl.2006.12.008
Shanker N et al (2011) Aurones: small molecule visible range fluorescent probes suitable for biomacromolecules. J Fluoresc 21:2173. https://doi.org/10.1007/s10895-011-0919-y
Popova A et al (2019) Aurones: synthesis and properties. Chem Heterocycl Compd 55(4/5):285. https://doi.org/10.1007/s10593-019-02457-x
Popova AV et al (2018) Efficient synthesis of aurone Mannich bases and evaluation of their antineoplastic activity in PC-3 prostate cancer cells. Chem Pap 72:2443–2456. https://doi.org/10.1007/s11696-018-0485-8
Guichaoua D et al (2019) UV irradiation induce NLO modulation in photochromic styrylquinoline-based polymers: computational and experimental studies. Org Electron 66:175–182. https://doi.org/10.1016/j.orgel.2018.12.022
Olyaei A, Javarsineh S, Sadeghpour M (2018) Green synthesis and Z/E-Isomerization of novel coumarin enamines induced by organic solvents. Chem Heterocycl Comp 54:934–939. https://doi.org/10.1007/s10593-018-2376-x
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2021 The Author(s), under exclusive license to Springer Nature Switzerland AG
About this paper
Cite this paper
Kharchenko, O. et al. (2021). Photochemical Properties of Side Chain Aurone Polymers. In: Fesenko, O., Yatsenko, L. (eds) Nanooptics and Photonics, Nanochemistry and Nanobiotechnology, and Their Applications . NANO 2020. Springer Proceedings in Physics, vol 264. Springer, Cham. https://doi.org/10.1007/978-3-030-74800-5_21
Download citation
DOI: https://doi.org/10.1007/978-3-030-74800-5_21
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-74799-2
Online ISBN: 978-3-030-74800-5
eBook Packages: Physics and AstronomyPhysics and Astronomy (R0)