Reaction Conditions, Photophysical, Electrochemical, Conductivity, and Thermal Properties of Polyazomethines

İsmet Kaya; Mehmet Gökpınar; Musa Kamacı

Macromolecular Research, Vol.25, No.7, 739-748, July, 2017

DOI10.1007/s13233-017-5072-2 Export Citation

Reaction Conditions, Photophysical, Electrochemical, Conductivity, and Thermal Properties of Polyazomethines

İsmet Kaya^{1, †}, Mehmet Gökpınar¹, and Musa Kamacı^{1, 2}

¹Polymer Synthesis and Analysis Lab., Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, 17020, Çanakkale, Turkey
²Department of Chemistry, Faculty of Sciences and Arts, Piri Reis University, 34940 Tuzla, Istanbul, Turkey

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In this paper, a series of Schiff bases and their polyazomethine derivatives were synthesized via condensation and oxidative polycondensation reactions of 4- aminophenol with 4-isopropylbenzaldehyde or 4-t-butylbenzaldehyde. Polymerization reaction conditions for polymerization yield of polyazomethines were investigated by changing some experimental parameters such as time and temperature using different oxidants like alkaline NaOCl (30%) and air. The structural characterizations of Schiff bases and polymers were performed using FT-IR, 1H NMR, 13C NMR and SEC techniques. Photophysical properties were studied UV-vis and photoluminescence spectroscopies. Electrochemical properties were also investigated cyclic voltammetry (CV) and electrochemical band gaps determined in the range 1.73 to 2.63 eV. Thermal properties of the compounds were investigated using TG-DTA and DSC techniques and char residue at 1000 °C determined between 3-6% and 39-34% for Schiff bases and polyazomethines, respectively. Moreover, conductivity measurements were done using four-point probe technique at both doped with iodine vapor and un-doped state.

Keywords:polyazomethine;schiff base;reaction conditions;conductivity;thermal properties

[References]

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Barik S, Bishop S, Skene WG, Mater. Chem. Phys., 129(1-2), 529 (2011)
Kaya I, Yıldırım M, Avcı A, Synth. Met., 160, 911 (2010)
Kim HJ, Lee JH, Lee M, Lee TS, React. Funct. Polym., 68(12), 1696 (2008)
Zaltariov MF, Cazacu M, Racles C, Musteata V, Vlad A, Airine A, J. Appl. Polym. Sci., 132, 41361 (2015)
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Ma H, Yip HL, Huang F, Jen AKY, Adv. Funct. Mater., 20(9), 1371 (2010)
Mallet C, Borgne ML, Starck M, Skene WG, Polym. Chem., 4, 250 (2013)
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Dineshkumar S, Muthusamy A, Chandrasekaran J, J. Mol. Struct., 1128, 730 (2017)
Senol D, Kolcu F, Kaya I, J. Fluoresc., 26, 1579 (2016)
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Baran NY, Karakisla M, Demir HO, Sacak M, J. Mol. Struct., 1123, 153 (2016)
Kaya I, Bilici A, Sacak M, Synth. Met., 159, 1414 (2009)
Dineshkumar S, Muthusamy A, Chitra P, Anand S, J. Adhes. Sci. Technol., 29(23), 2605 (2015)
Jarzabek B, Kaczmarczyk B, Jurusik J, Siwy M, Weszka J, J. Non-Cryst. Solids, 375, 13 (2013)
Grigoras M, Catanescu CO, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., 44, 131 (2004)
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Dufresne S, Skene WG, J. Phys. Org. Chem., 25, 211 (2012)
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Kamacı M, Avcı A, Kaya I, Prog. Org. Coat., 88, 325 (2015)
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Kaya I, Yıldırım M, Avcı A, Synth. Met., 160, 911 (2010)
Yildirim M, Kaya I, Polym. Bull., 71(12), 3067 (2014)
Kamacı M, Kaya I, J. Fluoresc., 25, 1339 (2015)
Kamacı M, Kaya I, J. Inorg. Organomet. Polym., 25, 1250 (2015)
Afzal S, Gul A, Akhter Z, J. Inorg. Organomet. Polym., 24, 321 (2014)
Senol D, Kolcu F, Kaya I, J. Fluoresc., 26, 1579 (2016)

[1] Sek D, Iwan A, Jarzabek B, Kaczmarczyk B, Kasperczyk J, Mazurak Z, Domanski M, Karon K, Lapkowski M, Macromolecules, 41(18), 6653 (2008)

[2] Barik S, Bishop S, Skene WG, Mater. Chem. Phys., 129(1-2), 529 (2011)

[3] Kaya I, Yıldırım M, Avcı A, Synth. Met., 160, 911 (2010)

[4] Kim HJ, Lee JH, Lee M, Lee TS, React. Funct. Polym., 68(12), 1696 (2008)

[5] Zaltariov MF, Cazacu M, Racles C, Musteata V, Vlad A, Airine A, J. Appl. Polym. Sci., 132, 41361 (2015)

[6] Zaltariov MF, Cazacu M, Shova S, Varganici CD, Vacareanu L, Musteata V, Airinei A, Des. Monomers Polym., 17, 668 (2014)

[7] Kamaci M, Kaya I, J. Taiwan Inst. Chem. Eng., 59, 536 (2016)

[8] Sicard L, Navarathne D, Skalski T, Skene WG, Adv. Funct. Mater., 23, 3549 (2013)

[9] Iwan A, Boharewicz B, Tazbir I, Malinowski M, Filapek M, Klab T, Luszczynska B, Glowacki I, Korona KP, Kaminska M, Wojtkiewicz J, Lewandowska M, Hreniak A, Sol. Energy, 117, 246 (2015)

[10] Bednarski H, G¡siorowski J, Domaski M, Hajduk B, Jurusik J, Jarz¡bek B, Weszka J, Acta Phys. Polym. A, 122, 1083 (2012)

[11] Ma H, Yip HL, Huang F, Jen AKY, Adv. Funct. Mater., 20(9), 1371 (2010)

[12] Mallet C, Borgne ML, Starck M, Skene WG, Polym. Chem., 4, 250 (2013)

[13] Guarin SAP, Bourgeaux M, Dufresne S, Skene WG, J. Org. Chem., 72, 2631 (2007)

[14] Barik S, Skene WG, Polym. Chem., 2, 1091 (2011)

[15] Guarin SAP, Skene WG, Mater. Lett., 61, 5102 (2007)

[16] Dineshkumar S, Muthusamy A, Chandrasekaran J, J. Mol. Struct., 1128, 730 (2017)

[17] Senol D, Kolcu F, Kaya I, J. Fluoresc., 26, 1579 (2016)

[18] Kaya I, Yıldırım M, Eur. Polym. J., 43, 127 (2007)

[19] Baran NY, Karakisla M, Demir HO, Sacak M, J. Mol. Struct., 1123, 153 (2016)

[20] Kaya I, Bilici A, Sacak M, Synth. Met., 159, 1414 (2009)

[21] Dineshkumar S, Muthusamy A, Chitra P, Anand S, J. Adhes. Sci. Technol., 29(23), 2605 (2015)

[22] Jarzabek B, Kaczmarczyk B, Jurusik J, Siwy M, Weszka J, J. Non-Cryst. Solids, 375, 13 (2013)

[23] Grigoras M, Catanescu CO, J. Macromol. Sci.-Rev. Macromol. Chem. Phys., 44, 131 (2004)

[24] Iwan A, Sek D, Prog. Polym. Sci, 33, 289 (2008)

[25] Dufresne S, Skene WG, J. Phys. Org. Chem., 25, 211 (2012)

[26] Ciechanowicz SG, Korona KP, Wolos A, Drabinska A, Iwan A, Tazbir I, Wojtkiewicz J, Kaminska M, J. Phys. Chem. C, 120, 11415 (2016)

[27] Bronnikov S, Kostromin S, Mustea V, Cozan V, Liq. Cryst., 42, 1102 (2015)

[28] Culhaoglu S, Kaya I, Polym. Korea, 39(2), 225 (2015)

[29] Kamacı M, Kaya I, J. Inorg. Organomet. Polym., 24, 803 (2014)

[30] Kaya I, Yıldırım M, Kamacı M, Eur. Polym. J., 45, 1586 (2009)

[31] Avci A, Kamaci M, Kaya I, Yildirim M, Mater. Chem. Phys., 163, 301 (2015)

[32] Kamacı M, Avcı A, Kaya I, Prog. Org. Coat., 88, 325 (2015)

[33] Navarchian AM, Hasanzadeh Z, Joulazadeh M, Adv. Polym. Technol., 32, 21356 (2013)

[34] Matyushov DV, Schmid R, Ladanyi BM, J. Phys. Chem. B, 101(6), 1035 (1997)

[35] Hein CD, Liu XM, Wang D, Pharm. Res., 25, 2216 (2008)

[36] Kamaci M, Kaya I, Polym. Eng. Sci., 54(7), 1664 (2014)

[37] Kaya I, Yıldırım M, Avcı A, Synth. Met., 160, 911 (2010)

[38] Yildirim M, Kaya I, Polym. Bull., 71(12), 3067 (2014)

[39] Kamacı M, Kaya I, J. Fluoresc., 25, 1339 (2015)

[40] Kamacı M, Kaya I, J. Inorg. Organomet. Polym., 25, 1250 (2015)

[41] Afzal S, Gul A, Akhter Z, J. Inorg. Organomet. Polym., 24, 321 (2014)

[42] Senol D, Kolcu F, Kaya I, J. Fluoresc., 26, 1579 (2016)