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YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+

Yıl 2015, Cilt: 3 Sayı: 4, 36 - 48, 01.12.2015

Öz

Bu çalışmada; yapısında pirol (Py) ve antrakinonu bir arada bulunduran yeni 1,5-(1-pirolil)-9,10-antrakinon monomeri sentezlenmiştir. Sentezlenen bu yeni monomerin yapısal karakterizasyonu Fourier Transform İnfrared Spektroskopisi (FTIR) ve 1H-NMR Spektroskopisi yöntemleriyle gerçekleştirilmiş, elektrokimyasal davranışı ise dönüşümlü voltametri (CV) yöntemiyle incelenmiştir. 1,5-(1-pirolil)-9,10-antrakinon monomeri TBAPF destek elektroliti içeren nitrobenzen çözücü ortamında sürekli gerilim taraması yapılarak ITO (indiyum kalay oksit) kaplı cam elektrot yüzeyinde elektrokimyasal olarak polimerleştirilmiştir. Üretilen yeni polimer filmin elektrokimyasal karakterizasyonu dönüşümlü voltametri ve kronoamperometri (CA) yöntemleriyle gerçekleştirilmiştir. Polimer filmin iletkenliği dört nokta iletkenlik ölçüm yöntemi ile ölçülmüş, morfolojik yapısı Taramalı Elektron Mikroskopisi (SEM) ile incelenmiştir. FTIR spektroskopisi ve UV görünür bölge absorpsiyon spektroskopisi ile spektroskopik analizler yapılmıştır. Üretilen polimer filmin elektrokromik özelliklerinin incelenmesi amacıyla optokimyasal çalışmalar yapılmıştır. Polimer filmin optik zıtlığı 750 nm’de % 50 olarak bulunmuştur. Polimerin iletkenliği 1.83x10-3 S/cm olarak ölçülmüştür. Polimer filmin rengi yükseltgenme sırasında laciverte, indirgenme sırasında koyu turuncuya yakın renk almıştır.

Kaynakça

  • Ak, M., Gacal, B., Kiskan, B., Yagci, Y., Toppare, L., 2008, ‚Enhancing electrochromic properties of polypyrrole by silsesquioxane nanocages‛, Polymer, Vol. 49, pp. 2201-2210.
  • Al-Omar, M.A., Infrared Spectroscopy, http://faculty.ksu.edu.sa/Alomar/Documents/IR.ppt, ziyaret tarihi: 03 Şubat 2015.
  • Arslan, A., Türkarslan, Ö., Tanyeli, C., Akhmedov, I.M., Toppare, L., 2001, ‚Electrochromic properties of a soluble conducting polymer: Poly(1-(4-fluorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole)‛, Materials Chemistry and Physics, Vol. 104, pp. 410-416.
  • Bagheri, H., Ayazi, Z., Naderi M., 2013, ‚Conductive polymer-based microextraction methods: a review‛, Anal. Chimica A, Vol. 767, pp. 1–13.
  • Bruice, P.Y., 2003, Organic Chemistry, http://wps.prenhall.com/wps/media/objects/724/741576/chapter_14.html, ziyaret tarihi: 3 Ocak 2015.
  • Coelho, E.C.S., Nascimento, V.B., Ribeiro, A.S., Navarro, M., 2014, ‚Electrochemical and optical properties of new electrochromic and fluorescent nitrobenzoyl polypyrrole derivatives‛, Electrochimica Acta, Vol. 123, pp. 441– 449.
  • Çamurlu, P., Gültekin, C., Bicil, Z., 2012, ‚Fast switching, high contrast multichromic polymers from alkyl-derivatized dithienylpyrrole and 3,4-ethylenedioxythiophene‛, Electrochimica Acta, Vol. 61, pp. 50-56.
  • Duan, F., Zhang, Q., Shi, D., Chen, M., 2013, ‚Enhanced visible light photocatalytic activity of Bi2WO6 via Modification with polypyrrole‛, App. Surf. Sci., Vol. 268, pp. 129– 135.
  • Ferrere, S., Zaban, A., Gregg, B.A., 1997, ‚Dye sensitization of nanocrystalline tin oxide by perylene derivatives‛, J. Phys. Chem. B, Vol. 101, pp. 4490-4493.
  • Huang, Y.M., Zhou, F., Deng, Y., Zhai, B., 2008, ‚Effects of 9,10-anthraquione-2sulfonic acid sodium on the conductivity of polypyrrole‛, Solid State Ionics, Vol. 179, pp. 1305-1309.
  • Li, Q., Zhang, C., Li, J., 2011, ‚Photocatalytic and microwave absorbing properties of polypyrrole/Fedoped TiO2 composite by in situ polymerization method‛, J. Alloys. Compd., Vol. 509, pp. 1953– 1957.
  • Li, Q., Zhang, C., Li, J., 2013, ‚Photocatalytic and microwave absorbing properties of polypyrrole/Fedoped TiO2 composite by in situ polymerization method‛, Journal of Alloys and Compounds, Vol. 509, pp. 1953-1957.
  • Liu, H., Zhang, G., Zhou, Y., Gao, M., Yang, F., 2013, ‚One-step potentiodynamic synthesis of poly(1,5- diaminoanthraquinone)/reduced graphene oxide nanohybrid with improved electrocatalytic activity‛, Journal of Materials Chemistry, Vol. 1, pp. 13902.
  • Morales, G.M., Llusa, M., Miras, M.C., Barbera, C., 1997, ‚Effects of high hydrochloric acid concentration on aniline chemical polymerization‛, Polymer, Vol. 38(20), pp. 5247-5250.
  • Paula, S., Domingo, H.V., Cesar, B., Maria, C.M., Artur, S.M., 2004, ‚Effect of electrolyte on the chemical polymerization of aniline‛, European Polymer Journal, Vol. 40, pp. 1445-1450.
  • Shaheen, S.E., Brabec, C.J., Sarıçiftçi, N.S., Padinger, F., Fromherz, T., Hummelen, J.C., 2001, ‚2.5% efficient organic plastic solar cells‛, Appl. Phys. Lett., Vol. 78, pp. 841-843.
  • Shinde, S.S., Gund, G.S., Dubal, D.P., Jambure, S.B., Lokhande, C.D., 2014, ‚Morphological modulation of polypyrrole thin films through oxidizing agents and their concurrent effect on supercapacitor performance‛, Electrochimica Acta, Vol. 119, pp. 1–10.
  • Silva, A.J.C., Nogueria, F.A.R., Tonholo, J., Ribeiro, A.S., 2011, ‚Dual-type electrochromic device based on polypyrrole and polythiophene derivatives‛, Solar Energy and Solar Cells, Vol. 95, pp. 2255-2259.
  • Skompska, M., Chmielewski, M.J., Tarajko, A., 2007, ‚Poly(1,8-diaminocarbazole)-A novel conducting polymer for sensor applications‛, Elektrochemistry Communucations, Vol. 9, pp. 540-544.
  • Sookhakian, M., Amin, Y.M., Baradaran, S., Tajabadi, M.T., Moradi Golsheikh, A., Basirun, W.J., 2014, ‚A layer-by-layer assembled graphene/zinc sulfide/polypyrrole thin-film electrode via electrophoretic deposition for solar cells‛, Thin Sol. Films, Vol. 552, pp. 204–211.
  • Sui, B., Fu, X., 2009, ‚Novel application 1-/2-phenyl substituted 9, 10-anthraquinones in solid electrochromic devices‛, J Solid State Electrochem, Vol. 13, pp. 1889-1895.
  • Tarkuc, S., Sahmetlioglu, E., Tanyeli, C., Akhmedov, I.M., Toppare, L., 2006, ‚A soluble conducting polymer:1-phenyl-2,5-di(2-thienyl)-1H-pyrrole and its electrochromic application‛, Electrochimica Acta, Vol. 51, pp. 5412-5419.
  • Tavoli, F., Alizadeh, N., 2014, ‚In situ UV-vis spectroelectrochemical study of dye doped nanostructure polypyrrole as electrochromic film‛, Journal of Electroanalytical Chemistry, Vol. 720-721, pp.128-133.
  • Wang, G., Fu, X., Huang, J., Wu, L., Du, Q., 2010, ‚Synthesis and spectroelectrochemical properties of two new dithienylpyrroles bearing athraquinone units and their polymer films‛, Electrochimica Acta, Vol. 55, pp. 6933-6940.
  • Yang, J., Dass, A., Rawashdeh, A.M., Sotiriou-Leventis, C., Panzner, M.J., Tyson, D.S., Kinder, J.D., Leventis, N., 2004, ‚Arylethynyl substituted 9,10-anthraquinones: Tunable stokes shifts by substitution and solvent polarity‛, Chem. Mater., Vol. 16, pp. 3457-3468.
  • Zhang, C., Li, Q., Li, J., 2010, ‚Synthesis and characterization of polypyrrole/TiO2 composite by In Situ polymerization method‛, Synth. Met., Vol. 160, pp.1699–1703.
  • Zhang, S., Chen, Q., Wang, Y., Guo, L., 2012, ‚Synthesis and photoactivity of CdS photocatalysts modified by polypyrrole‛, Int. J. Hyd. En., Vol. 37, pp. 13030-13036

A Novel Electrochromic Polymer: Poly[1,5-(1-Pyrrolyl)-9,10-Anthraquinone]

Yıl 2015, Cilt: 3 Sayı: 4, 36 - 48, 01.12.2015

Öz

In this study; a novel monomer 1,5-(1-pyrrolyl)-9,10-anthraquinone which contains pyrrole (Py) and anthraquinone was synthesized. The structure of the synthesized novel monomer was characterized by Fourier Transform Infrared Spectroscopy (FTIR) and 1H-NMR Spectroscopy methods; electrochemical behavior of the monomer was investigated by cyclic voltammetry (CV) method. Electropolymerization of 1,5-(1-pyrrolyl)-9,10-anthraquinone monomer in nitrobenzene solvent medium that contains supporting electrolyte TBAPF was carried out on ITO-coated glass electrode surface through continuous scanning of operating voltage. The produced novel polymer film’s electrochemical characterization was performed with cyclic voltammetry and chronoamperometry (CA) methods. The electrical conductivity of the polymer was measured by four-point conductivity method; the morphology of the polymer was analyzed by scanning electron microscopy (SEM). Spectroscopic analysis was carried out by FTIR spectroscopy and UV-Vis absorption spectroscopy. Some optoelectrochemical studies were done to investigate polymer film’s electrochromic properties. Optic contrast of the polymer film was found % 50 at 750 nm. Polymer conductivity was measured range of 1.83x10-3 S/cm. Polymer film’s color was close to dark orange when the polymer was reduced and color of the polymer film was dark blue tone while the polymer was oxidizing.

Kaynakça

  • Ak, M., Gacal, B., Kiskan, B., Yagci, Y., Toppare, L., 2008, ‚Enhancing electrochromic properties of polypyrrole by silsesquioxane nanocages‛, Polymer, Vol. 49, pp. 2201-2210.
  • Al-Omar, M.A., Infrared Spectroscopy, http://faculty.ksu.edu.sa/Alomar/Documents/IR.ppt, ziyaret tarihi: 03 Şubat 2015.
  • Arslan, A., Türkarslan, Ö., Tanyeli, C., Akhmedov, I.M., Toppare, L., 2001, ‚Electrochromic properties of a soluble conducting polymer: Poly(1-(4-fluorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole)‛, Materials Chemistry and Physics, Vol. 104, pp. 410-416.
  • Bagheri, H., Ayazi, Z., Naderi M., 2013, ‚Conductive polymer-based microextraction methods: a review‛, Anal. Chimica A, Vol. 767, pp. 1–13.
  • Bruice, P.Y., 2003, Organic Chemistry, http://wps.prenhall.com/wps/media/objects/724/741576/chapter_14.html, ziyaret tarihi: 3 Ocak 2015.
  • Coelho, E.C.S., Nascimento, V.B., Ribeiro, A.S., Navarro, M., 2014, ‚Electrochemical and optical properties of new electrochromic and fluorescent nitrobenzoyl polypyrrole derivatives‛, Electrochimica Acta, Vol. 123, pp. 441– 449.
  • Çamurlu, P., Gültekin, C., Bicil, Z., 2012, ‚Fast switching, high contrast multichromic polymers from alkyl-derivatized dithienylpyrrole and 3,4-ethylenedioxythiophene‛, Electrochimica Acta, Vol. 61, pp. 50-56.
  • Duan, F., Zhang, Q., Shi, D., Chen, M., 2013, ‚Enhanced visible light photocatalytic activity of Bi2WO6 via Modification with polypyrrole‛, App. Surf. Sci., Vol. 268, pp. 129– 135.
  • Ferrere, S., Zaban, A., Gregg, B.A., 1997, ‚Dye sensitization of nanocrystalline tin oxide by perylene derivatives‛, J. Phys. Chem. B, Vol. 101, pp. 4490-4493.
  • Huang, Y.M., Zhou, F., Deng, Y., Zhai, B., 2008, ‚Effects of 9,10-anthraquione-2sulfonic acid sodium on the conductivity of polypyrrole‛, Solid State Ionics, Vol. 179, pp. 1305-1309.
  • Li, Q., Zhang, C., Li, J., 2011, ‚Photocatalytic and microwave absorbing properties of polypyrrole/Fedoped TiO2 composite by in situ polymerization method‛, J. Alloys. Compd., Vol. 509, pp. 1953– 1957.
  • Li, Q., Zhang, C., Li, J., 2013, ‚Photocatalytic and microwave absorbing properties of polypyrrole/Fedoped TiO2 composite by in situ polymerization method‛, Journal of Alloys and Compounds, Vol. 509, pp. 1953-1957.
  • Liu, H., Zhang, G., Zhou, Y., Gao, M., Yang, F., 2013, ‚One-step potentiodynamic synthesis of poly(1,5- diaminoanthraquinone)/reduced graphene oxide nanohybrid with improved electrocatalytic activity‛, Journal of Materials Chemistry, Vol. 1, pp. 13902.
  • Morales, G.M., Llusa, M., Miras, M.C., Barbera, C., 1997, ‚Effects of high hydrochloric acid concentration on aniline chemical polymerization‛, Polymer, Vol. 38(20), pp. 5247-5250.
  • Paula, S., Domingo, H.V., Cesar, B., Maria, C.M., Artur, S.M., 2004, ‚Effect of electrolyte on the chemical polymerization of aniline‛, European Polymer Journal, Vol. 40, pp. 1445-1450.
  • Shaheen, S.E., Brabec, C.J., Sarıçiftçi, N.S., Padinger, F., Fromherz, T., Hummelen, J.C., 2001, ‚2.5% efficient organic plastic solar cells‛, Appl. Phys. Lett., Vol. 78, pp. 841-843.
  • Shinde, S.S., Gund, G.S., Dubal, D.P., Jambure, S.B., Lokhande, C.D., 2014, ‚Morphological modulation of polypyrrole thin films through oxidizing agents and their concurrent effect on supercapacitor performance‛, Electrochimica Acta, Vol. 119, pp. 1–10.
  • Silva, A.J.C., Nogueria, F.A.R., Tonholo, J., Ribeiro, A.S., 2011, ‚Dual-type electrochromic device based on polypyrrole and polythiophene derivatives‛, Solar Energy and Solar Cells, Vol. 95, pp. 2255-2259.
  • Skompska, M., Chmielewski, M.J., Tarajko, A., 2007, ‚Poly(1,8-diaminocarbazole)-A novel conducting polymer for sensor applications‛, Elektrochemistry Communucations, Vol. 9, pp. 540-544.
  • Sookhakian, M., Amin, Y.M., Baradaran, S., Tajabadi, M.T., Moradi Golsheikh, A., Basirun, W.J., 2014, ‚A layer-by-layer assembled graphene/zinc sulfide/polypyrrole thin-film electrode via electrophoretic deposition for solar cells‛, Thin Sol. Films, Vol. 552, pp. 204–211.
  • Sui, B., Fu, X., 2009, ‚Novel application 1-/2-phenyl substituted 9, 10-anthraquinones in solid electrochromic devices‛, J Solid State Electrochem, Vol. 13, pp. 1889-1895.
  • Tarkuc, S., Sahmetlioglu, E., Tanyeli, C., Akhmedov, I.M., Toppare, L., 2006, ‚A soluble conducting polymer:1-phenyl-2,5-di(2-thienyl)-1H-pyrrole and its electrochromic application‛, Electrochimica Acta, Vol. 51, pp. 5412-5419.
  • Tavoli, F., Alizadeh, N., 2014, ‚In situ UV-vis spectroelectrochemical study of dye doped nanostructure polypyrrole as electrochromic film‛, Journal of Electroanalytical Chemistry, Vol. 720-721, pp.128-133.
  • Wang, G., Fu, X., Huang, J., Wu, L., Du, Q., 2010, ‚Synthesis and spectroelectrochemical properties of two new dithienylpyrroles bearing athraquinone units and their polymer films‛, Electrochimica Acta, Vol. 55, pp. 6933-6940.
  • Yang, J., Dass, A., Rawashdeh, A.M., Sotiriou-Leventis, C., Panzner, M.J., Tyson, D.S., Kinder, J.D., Leventis, N., 2004, ‚Arylethynyl substituted 9,10-anthraquinones: Tunable stokes shifts by substitution and solvent polarity‛, Chem. Mater., Vol. 16, pp. 3457-3468.
  • Zhang, C., Li, Q., Li, J., 2010, ‚Synthesis and characterization of polypyrrole/TiO2 composite by In Situ polymerization method‛, Synth. Met., Vol. 160, pp.1699–1703.
  • Zhang, S., Chen, Q., Wang, Y., Guo, L., 2012, ‚Synthesis and photoactivity of CdS photocatalysts modified by polypyrrole‛, Int. J. Hyd. En., Vol. 37, pp. 13030-13036
Toplam 27 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Diğer ID JA47AJ52VU
Bölüm Makaleler
Yazarlar

Sultan Şule Doğu Bu kişi benim

Handan Kamış Bu kişi benim

Bircan Haspulat Bu kişi benim

Yayımlanma Tarihi 1 Aralık 2015
Yayımlandığı Sayı Yıl 2015 Cilt: 3 Sayı: 4

Kaynak Göster

APA Doğu, S. Ş., Kamış, H., & Haspulat, B. (2015). YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+. Selçuk Üniversitesi Mühendislik, Bilim Ve Teknoloji Dergisi, 3(4), 36-48.
AMA Doğu SŞ, Kamış H, Haspulat B. YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+. sujest. Aralık 2015;3(4):36-48.
Chicago Doğu, Sultan Şule, Handan Kamış, ve Bircan Haspulat. “YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+”. Selçuk Üniversitesi Mühendislik, Bilim Ve Teknoloji Dergisi 3, sy. 4 (Aralık 2015): 36-48.
EndNote Doğu SŞ, Kamış H, Haspulat B (01 Aralık 2015) YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+. Selçuk Üniversitesi Mühendislik, Bilim Ve Teknoloji Dergisi 3 4 36–48.
IEEE S. Ş. Doğu, H. Kamış, ve B. Haspulat, “YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+”, sujest, c. 3, sy. 4, ss. 36–48, 2015.
ISNAD Doğu, Sultan Şule vd. “YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+”. Selçuk Üniversitesi Mühendislik, Bilim Ve Teknoloji Dergisi 3/4 (Aralık 2015), 36-48.
JAMA Doğu SŞ, Kamış H, Haspulat B. YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+. sujest. 2015;3:36–48.
MLA Doğu, Sultan Şule vd. “YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+”. Selçuk Üniversitesi Mühendislik, Bilim Ve Teknoloji Dergisi, c. 3, sy. 4, 2015, ss. 36-48.
Vancouver Doğu SŞ, Kamış H, Haspulat B. YENİ BİR ELEKTROKROMİK POLİMER: POLİ*1,5-(1-PİROLİL)-9,10-ANTRAKİNON+. sujest. 2015;3(4):36-48.

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