New monomers for (bi)pyridine-containing polymers

A. P. Krinochkin; M. I. Savchuk; E. S. Starnovskaya; Y. K. Shtaitz; D. S. Kopchuk; I. L. Nikonov; I. S. Kovalev; G. V. Zyryanov; V. L. Rusinov; O. N. Chupakhin

doi:10.15826/chimtech.2020.7.4.13

New monomers for (bi)pyridine-containing polymers

A. P. Krinochkin, M. I. Savchuk, E. S. Starnovskaya, Y. K. Shtaitz, D. S. Kopchuk, I. L. Nikonov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin

Abstract

Convenient methods for the synthesis of three monomers based on functionalized (bi)pyridines with using “1,2,4-triaizine” methodology have been developed.

Keywords

monomers; 1,2,4-triazines; (bi)pyridines; inverse demand Diels-Alder reaction

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References

Li ZR, editor. Organic Light-Emitting Materials and Devices. Boca Raton: CRC Press, 2015. 813 p.

Wang C, Kilitziraki M, MacBride JAH, Bryce MR., Horsburgh LE, Sheridan AK, Monkman AP, Samuel IDW. Tuning the optoelectronic properties of pyridine-containing polymers for light-emitting devices. Adv Mater. 2000;12:217–22. doi:10.1002/(SICI)1521-4095(200002)12:3<217::AID-ADMA217>3.0.CO;2-Y

Sato Y, Kagotani M, Yamamoto T, Souma Y. Novel Effective Poly(2,2′-Bipyridine-5,5′-Diyl)-CuCl2 Catalyst for Synthesis of Dimethyl Carbonate (DMC) by Oxidative Carbonylation of Methanol. Appl Catal A-Gen. 1999;185:219–26. doi:10.1016/S0926-860X(99)00175-1

Xiao L, Zhang H, Jana T, Scanlon E, Chen R, Choe E-W, Ramanathan LS, Yu S, Denicewicz BC. Synthesis and characterization of pyridine-based polybenzimidazoles for high temperature polymer electrolyte membrane fuel cell applicationsx. Fuel cells. 2005;5:287–95. doi:10.1002/fuce.200400067

Yang L, Mihali V-A, Brandell D, Strømme M, Sjödin M. Conjugated Pyridine-Based Poly-mers Characterized as Conductivity Carrying Components in Anode Materials. J Phys Chem C. 2014;118:25956–63. doi:10.1021/jp509606c

Kozhevnikov VN, Kozhevnikov DN, Shabunina OV, Rusinov VL, Chupakhin ON. An effi-cient route to 5-(hetero)aryl-2,4′- and 2,2′-bipyridines through readily available 3-pyridyl-1,2,4-triazines. Tetrahedron Lett. 2005;46:1791–3. doi:10.1016/j.tetlet.2005.01.135

Pabst GR, Sauer J. A new and simple 'LEGO' system for the synthesis of 2,6-oligopyridines. Tetrahedron Lett. 1998;39:6687–90. doi:10.1016/S0040-4039(98)01437-3

Rykowski A, Branowska D, Kielak J. A novel one-pot synthesis of annulated 2,2′-bipyridine ligands by inverse electron demand Diels–Alder reaction of 5,5′-bi-1,2,4-triazines. Tetrahedron Lett. 2000;41:3657–9. doi:10.1016/S0040-4039(00)00436-6

Kozhevnikov VN, Shabunina OV, Kopchuk DS, Ustinova MM, König B, Kozhevnikov DN. Facile synthesis of 6-aryl-3-pyridyl-1,2,4-triazines as a key step toward highly fluorescent 5-substituted bipyridines and their Zn(II) and Ru(II) complexes. Tetrahedron. 2008;64:8963–73. doi:10.1016/j.tet.2008.06.040

Starnovskaya ES, Kopchuk DS, Khasanov AF, Tanya OS, Santra S, Giri K, Rahman M, Ko-valev IS, Zyryanov GV, Majeed A, Charushin VN. Synthesis and photophysics of new unsym-metrically substituted 5,5′-diaryl-2,2′-bypiridine-based “push-pull” fluorophores. Dyes Pigm. 2019;162:324–30. doi:10.1016/j.dyepig.2018.10.040

Kopchuk DS, Chepchugov NV, Starnovskaya ES, Khasanov AF, Krinochkin AP, Santra S, Zyryanov GV, Das P, Majee A, Rusinov VL, Charushin VN. Synthesis and optical properties of new 2-(5-arylpyridine-2-yl)-6-(het)arylquinoline-based “push-pull” fluorophores. Dyes Pigm. 2019;167:151–6. doi 10.1016/j.dyepig.2019.04.029

Kozhevnikov VN, Ustinova MM, Slepukhin PA, Santoro A, Bruce DW, Kozhevnikov DN. From 1,2,4-triazines towards substituted pyridines and their cyclometallated Pt complexes. Tet-rahedron Lett. 2008;49:4096–8. doi:10.1016/j.tetlet.2008.04.138

Saraswathi TV, Srinivasan VR. A novel synthesis of 1,2,4-triazines. Tetrahedron Lett. 1971;12:2315–6. doi:10.1016/S0040-4039(01)96849-2

Saraswathi TV, Srinivasan VR. Syntheses and spectral characteristics of 6-mono-, 3,6-di and 3,5,6-trisubstituted-1,2,4-triazines. Tetrahedron. 1977;33:1043–51. doi:10.1016/0040-4020(77)80223-8

Shtaitz YaK, Savchuk MI, Kopchuk DS, Taniya OS, Santra S, Zyryanov GV, Suvorova AI, Rusinov VL, Chupakhin ON. Efficient Synthesis of Methyl 6-(6-Aryl-1,2,4-triazin-3-yl)pyridine-2-carboxylates. Russ J Org Chem. 2020;56:548–51. doi:10.1134/S1070428020030306

Khan MS, Al-Mandhary MRA, Al-Suti MK. Feeder N, Nahar S, Koehler A, Friend RH, Wil-son PJ, Raithby PR. Synthesis, characterisation and electronic properties of a series of plati-num(II) poly-ynes containing novel thienyl-pyridine linker groups. Dalton Trans. 2002;12:2441–8. doi:10.1039/B201073A

Hu B, Fu S-J, Xu F, Tao T, Zhu H-Y, Cao K-S, Huang W, You X-Z. Linear heterocyclic ar-omatic fluorescence compounds having various donor-acceptor spacers prepared by the combi-nation of carbon-carbon bond and carbon-nitrogen bond cross-coupling reactions. J Org Chem. 2011;76:4444–56. doi:10.1021/jo200065d

DOI: https://doi.org/10.15826/chimtech.2020.7.4.13

Copyright (c) 2020 Krinochkin A.P., Savchuk M.I., Starnovskaya E.S., Shtaitz Y.K., Kopchuk D.S., Nikonov I.L., Kovalev I.S., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Chimica Techno Acta, 2014-2024
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