Synthesis and Characterization A Novel Thermally Stable Schiff Base Oligomer: Investigation of Conductivity Properties

This paper presents design of a novel Schiff base, 2,2'-{[1,2-di(pyridin-2-yl)ethane-1,2-diylidene]bis(azanylylidene)}diphenol (2,2-DBD), and its oligophenol, Oligo-(2,2'-{[1,2-di(pyridin-2-yl)ethane-1,2-diylidene]bis(azanylylidene)}diphenol) O(2,2-DBD), synthesized with NaOCl and O2 oxidants in aqueous alkaline medium by oxidative polycondensation reaction. The effects of oxidant type, polymerization temperature and time on oligomer yield were determined. Characterization of the structures of the synthesized (2,2-DBD) and O(2,2-DBD) were done by UV-Vis, FTIR and 1HNMR techniques. Also, thermal degradations of the monomer and oligomer were investigated TG-DTG analysis and it was determined that the oligomer thermally stable up to 1200 ˚C. Additionally, electrical conductivity of the oligomer was improved by doping with iodine at 20 ˚C and the conductivity of the oligomer reached to 9x10-4 S/cm by increasing 107 at the end of the 48 h doping time fold according to its undoped form.

Keywords:

Conductivity, oxidative polycondensation oligophenols,

PDF

___

1. Spiliopoulos IK, Mikroyannidis JA. Soluble, Rigid-Rod Polyamide, Polyimides, and Polyazomethine with Phenyl Pendent Groups Derived from 4,4‘‘-Diamino-3,5,3‘‘,5‘‘-tetraphenyl-p-terphenyl. Macromolecules. 1996;29(16):5313-9. DOI: 10.1021/ma9602233.
2. Aly KI, Khalaf AA. New polymer syntheses. IX. Synthesis and properties of new conducting polyazomethine polymers containing main chain cycloalkanone and pyridine moieties. Journal of Applied Polymer Science. 2000;77(6):1218-29. DOI:10.1002/1097-4628(20000808)77:6<1218::AID-APP6>3.0.CO;2-G.
3. Jae-Wook K, Jang-Joo K, Jinkyu K, Xiangdan L, Myong-Hoon L. Low-loss and thermally stable TE-mode selective polymer waveguide using photosensitive fluorinated polyimide. IEEE Photonics Technology Letters. 2002;14(9):1297-9. DOI: 10.1109/LPT.2002.801088
4. Iwan A, Boharewicz B, Tazbir I, Malinowski M, Filapek M, Kłąb T, et al. New environmentally friendly polyazomethines with thiophene rings for polymer solar cells. Solar Energy. 2015;117:246-59. DOI: 10.1016/j.solener.2015.03.051.
5. Niu H, Huang Y, Bai X, Li X, Zhang G. Study on crystallization, thermal stability and hole transport properties of conjugated polyazomethine materials containing 4,4′-bisamine-triphenylamine. Materials Chemistry and Physics. 2004;86(1):33-7. DOI: 10.1016/j.matchemphys.2004.01.023.
6. Iwan A, Palewicz M, Chuchmala A, Sikora A, Gorecki L, Sek D. Opto(electrical) properties of triphenylamine-based polyazomethine and its blend with 6,6 -phenyl C-61 butyric acid methyl ester. High Perform Polym. 2013;25(7):832-42. DOI: 10.1177/0954008313486818.
7. Kamacı M, Kaya İ. 2,4-Diamino-6-Hydroxypyrimidine Based Poly(azomethine-Urethane): Synthesis and Application as a Fluorescent Probe for Detection of Cu2+ in Aqueous Solution. Journal of Fluorescence. 2015;25(5):1339-49. DOI: 10.1007/s10895-015-1624-z.
8. Marin L, Cozan V, Bruma M, Grigoras VC. Synthesis and thermal behaviour of new poly(azomethine-ether). European Polymer Journal. 2006;42(5):1173-82. DOI: 10.1016/j.eurpolymj.2005.11.010.
9. Sȩk D. Liquid crystalline properties of new poly(azomethine esters). European Polymer Journal. 1984;20(9):923-6. DOI: 10.1016/0014-3057(84)90174-5.
10. Cozan V, Butuc E, Stoleriu A, Rusa M, Rusu M, Ni Y, et al. Poly(Azomethine Sulfones) with Thermotropic Liquid Crystalline Behavior. Journal of Macromolecular Science, Part A. 1995;32(7):1243-62. DOI: 10.1080/10601329508009352.
11. Yılmaz Baran N, Demir HÖ, Kostekçi S, Sacak M. Poly-2-[(4-methylbenzylidene)amino]phenol: Investigation of thermal degradation and antimicrobial properties. Journal of Applied Polymer Science. 2015;132(14):n/a-n/a. DOI: 10.1002/app.41758
12. Demir HÖ. Ketimine substituted polyphenol: Synthesis, characterization and investigation of its thermal and electrochemical properties. Journal of Applied Polymer Science. 2013;127(6):5037-44. DOI: 10.1002/app.38122.
13. Demetgül C, Delikanlı A, Sarıbıyık OY, Karakaplan M, Serin S. Schiff Base Polymers Obtained by Oxidative Polycondensation and Their Co(II), Mn(II) and Ru(III) Complexes: Synthesis, Characterization and Catalytic Activity in Epoxidation of Styrene. Designed Monomers and Polymers. 2012;15(1):75-91. DOI: 10.1163/156855511X606164.
14. Kaya İ, Yıldırım M, Avcı A. Synthesis and characterization of fluorescent polyphenol species derived from methyl substituted aminopyridine based Schiff bases: The effect of substituent position on optical, electrical, electrochemical, and fluorescence properties. Synthetic Metals. 2010;160(9–10):911-20. DOI: 10.1016/j.synthmet.2010.01.044.
15. Yıldırım M, Kaya İ. Synthesis and characterizations of poly(ether)/poly(phenol)s including azomethine coupled benzothiazole side chains: the effect of reaction conditions on the structure, optical, electrochemical, electrical and thermal properties. Polymer Bulletin. 2014;71(12):3067-84. DOI: 10.1007/s00289-014-1238-7.
16. Kaya, Emdi D, Saçak M. Synthesis, Characterization and Antimicrobial Properties of Oligomer and Monomer/Oligomer–Metal Complexes of 2-[(Pyridine-3-yl-methylene)amino]phenol. J Inorg Organomet Polym. 2009;19(3):286-97. DOI: 10.1007/s10904-009-9270-z.
17. Kaya İ, Aydın A. A new approach for synthesis of electroactive phenol based polymer: 4-(2,5-Di(thiophen-2-yl)-1H-pyrrol-1-yl)phenol and its oxidative polymer. Progress in Organic Coatings. 2012;73(2):239-49. DOI: 10.1016/j.porgcoat.2011.11.008.
18. Eker B, Zagorevski D, Zhu G, Linhardt RJ, Dordick JS. Enzymatic polymerization of phenols in room-temperature ionic liquids. Journal of Molecular Catalysis B: Enzymatic. 2009;59(1):177-84. DOI: 10.1016/j.molcatb.2009.02.018.
19. Mart H. Oxidative polycondensation reaction. Designed Monomers and Polymers. 2006;9(6):551-88. DOI: 10.1163/156855506778944055.
20. Yılmaz Baran N, Saçak M. Synthesis, characterization and molecular weight monitoring of a novel Schiff base polymer containing phenol group: Thermal stability, conductivity and antimicrobial properties. Journal of Molecular Structure. 2017;1146(Supplement C):104-12. DOI: 10.1016/j.molstruc.2017.05.120.
21. Yılmaz Baran N, Karakışla M, Demir HÖ, Saçak M. Synthesis, characterization, conductivity and antimicrobial study of a novel thermally stable polyphenol containing azomethine group. Journal of Molecular Structure. 2016;1123:153-61. DOI: 10.1016/j.molstruc.2016.06.028.
22. Özbülbül A, Mart H, Tunçel M, Serin S. A new soluble Schiff base polymer with a double azomethine group synthesized by oxidative polycondensation. Designed Monomers and Polymers. 2006;9(2):169-79. DOI: 10.1163/156855506776382655
23. Cazacu M, Marcu M, Vlad A, Rusu GI, Avadanei M. Chelate polymers. VI. New copolymers of the some siloxane containing bis(2,4-dihydroxybenzaldehyd-imine)Me2+ with bis(p-carboxyphenyl)diphenylsilane. Journal of Organometallic Chemistry. 2004;689(19):3005-11. DOI: 10.1016/j.jorganchem.2004.05.051.
24. Diaz FR, Moreno J, Tagle LH, East GA, Radic D. Synthesis, characterization and electrical properties of polyimines derived from selenophene. Synthetic Metals. 1999;100(2):187-93. DOI: 10.1016/S0379-6779(98)01484-2.
25. Kaya I, Bilici A, Sacak M. New conjugated azomethine oligomers obtained from bis-(hydroxyphenyl)methylenediamine via oxidative polycondensation and their complexes with metals. Synthetic Metals. 2009;159(14):1414-21. DOI: 10.1016/j.synthmet.2009.03.014.