Thermostable fluorinated aromatic polyethers as materials for modern microelectronics and light-responsive elements

According to the materials of report at the meeting of the Presidium of the NAS of Ukraine, May 3, 2023

Authors

DOI:

https://doi.org/10.15407/visn2023.07.072

Keywords:

fluorinated poly(arylene ether)s, dielectric properties, 5G technology, light-responsive polymers, azobenzene, azomethine group, reversible photoisomerization, photoinduced birefringence

Abstract

We propose a strategy for the synthesis of fluorinated poly(arylene ether)s (FPAEs) of linear and cross-linked hybrid organic-inorganic macromolecular structures, which are characterized by high thermal stability. The synthesized polymers could afford flexible and strong films with a low dielectric constant (1.86—2.75 at 10 kHz) and dissipation factor (0.0013—0.0037 at 10 kHz). This allows their use as interlayer dielectrics in integrated circuits for modern micro- and nanoelectronics, in particular in the fabrication of printed circuit boards for 5G communication technology. The 5G mobile network is envisioned to be the communication standard to effectively support diverse operations and applications of unmanned aerial vehicles or autonomous demining robots. Next, we developed a synthetic route for new meta-linked FPAEs having both azobenzene and azomethine optically active groups. Because of their unique chemical structures, the obtained light-sensitive FPAEs exhibited good solubility in polar aprotic solvents and the ability to form mechanically stable free-standing films in which trans-cis photoisomerization of azo/azomethine groups occurred under UV irradiation. Polymers were capable of photoinduced birefringence by lasers of different wavelengths (in particular, 405 or 532 nm) and recording of polarization gratings. The azo-azomethine polymers are promising as thermostable optically active components in various sensors, photo-orienting surfaces, in the creation of tactile holograms, electro-optical converters/modules, in medicine, etc. The resulting systems can be used in soft robotics and for vehicles (unmanned aerial vehicles, robots for demining).

References

Tsui G.Ch., Hu J. Organofluorine Chemistry. Asian Journal of Organic Chemistry. 2019. 8(5): 566—567. https://doi.org/10.1002/ajoc.201900271

Wang J., Sanchez-Rosello M., Acena J.L., del Pozo C., Sorochinsky A.E., Fustero S., Soloshonok V.A., Liu H. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001—2011). Chemical Reviews. 2014. 114(4): 2432—2506. https://doi.org/10.1021/cr4002879

Fujiwara T., O’Hagan D. Successful fluorine-containing herbicide agrochemicals. Journal of Fluorine Chemistry. 2014. 167: 16—29. https://doi.org/10.1016/j.jfluchem.2014.06.014

Purser S., Moore P.R., Swallow S., Gouverneu V. Fluorine in medicinal chemistry. Chemical Society Reviews. 2008. 37(2): 320—330. https://doi.org/10.1039/B610213C

Pagliaro M., Ciriminna R. New fluorinated functional materials. Journal of Materials Chemistry. 2005. 15(47): 4981—4991. https://doi.org/10.1039/B507583C

Uneyama K. Organofluorine chemistry. John Wiley & Sons, 2008. https://doi.org/10.1002/9780470988589

Hideki A., Uneyama K. C-F bond activation in organic synthesis. Chemical Reviews. 2009. 109(5): 2119—2183. https://doi.org/10.1021/cr800388c

Liu J., Ni Ch., Li Ya, Zhang L., Wang G., Hu J. Facile preparation of difluoromethyl- and monofluoromethyl-containing amides via Ritter reaction. Tetrahedron Letters. 2006. 47(38): 6753—6756. https://doi.org/10.1016/j.tetlet.2006.07.079

Zhou Ye. Material foundation for future 5G technology. Accounts of Materials Research. 2021. 2(5): 306—310. https://doi.org/10.1021/accountsmr.0c00087

Berger R. et al. Organic fluorine compounds: a great opportunity for enhanced materials properties. Chemical Society Reviews. 2011. 40(7): 3496—3508. https://doi.org/10.1039/C0CS00221F

Sun J. et al. Azobenzene‐Based Photomechanical Biomaterials. Advanced NanoBiomed Research. 2021. 1(9): 2100020. https://doi.org/10.1002/anbr.202100020

Belowich M.E., Stoddart J.F. Dynamic imine chemistry. Chemical Society Reviews. 2012. 41(6): 2003—2024. https://doi.org/10.1039/C2CS15305J

Kovalchuk A.I. et al. Photoactive fluorinated poly(azomethine)s with azo groups in the main chain for optical storage applications and controlling liquid crystal orientation. ACS Applied Polymer Materials. 2019. 2(2): 455—463. https://doi.org/10.1021/acsapm.9b00906

Leigh D.A. Genesis of the nanomachines: the 2016 Nobel prize in chemistry. Angewandte Chemie International Edition. 2016. 55(47): 14506—14508. https://doi.org/10.1002/anie.201609841

Published

2023-07-21