Abstract
A novel organic molecule of 9H-carbazole-9-carbothioic methacrylic thioanhydride (CzCS2metac) was synthesized by incorporating CS2 and methacrylate groups into the carbazole monomer structure. CzCS2metac was characterized by FTIR, 1H-NMR and 13C-NMR spectroscopy. CzCS2metac was electropolymerized in 0.1 M tetraethylammonium tetrafluoroborate (TEABF4)/acetonitrile (CH3CN) on glassy carbon electrode (GCE). The characterization of the electrocoated P(CzCS2metac)/CFME thin film was studied by various techniques, such as cyclic voltammetry, scanning electron microscopy–energy-dispersive X-ray analysis and electrochemical impedance spectroscopy. The specific capacitance (C sp) of P(CzCS2metac)/MWCNT/GCE in the scan rate of 20 mV s−1 (C sp = 38.48 F g−1 from area formula, C sp = 38.52 F g−1 from charge formula) was increased ~15.66 and ~15.64 times in area and charge formulas compared to P(CzCS2metac)/GCE (C sp = 2.46 F g−1 from area and charge formulas). The same results were also obtained from Nyquist graphs. The specific capacitance value of composite film (C sp = 1.09 × 10−3 F) is ~15.66 times higher than the polymer film (C sp = 6.92 × 10−5 F). The composite film may be used as supercapacitor electrode material in energy storage devices.
Similar content being viewed by others
References
McGrath JE, Rasmussen L, Shultz AR, Shobha HK, Sankarapandian M, Glass T, Long TE, Pasquale AJ (2006) Novel carbazole phenoxy-based methacrylates to produce high-refractive index polymers. Polymer 47:4042–4057
Roncali J (1992) Conjugated poly(thiophenes)-synthesis, functionalization, and applications. Chem Rev 92(4):711–738
Li XG, Huang MR, Duan W, Yang YL (2002) Novel multifunctional polymers from aromatic diamines by oxidative polymerizations. Chem Rev 102(9):2925–3030
Zhao M, Zhang HT, Ma FN, Zhang Y, Guo XZ, Zhang HQ (2013) Efficient synthesis of monodisperse, highly crosslinked, and “living” functional polymer microspheres by the ambient temperature iniferter- induced “living” radical precipitation polymerization. J Polym Sci Part A Polym Chem 51(9):1983–1998
Sarac AS, Parlak EA, Serhatli E, Cakir T (2007) Microcomposite electrochemical capacitor: electrocoating of poly[N-hydroxymethylcarbazole] onto carbon fiber, surface morphology, spectroscopic surface characterization, electrochemical impedance spectroscopy. J Appl Polym Sci 104(1):238–246
Ates M, Uludag N (2010) Synthesis and electropolymerization of 9-(4-vinylbenzyl)-9H-carbazole on carbon fiber microelectrode: capacitive behavior of poly(9-(4-vinylbenzyl)-9H-carbazole). Fibers Polym 11(3):331–337
Lmimouni K, Legrand C, Chapoton A (1998) Optical and electrical characterizations of poly(N-alkylcarbazole) light-emitting diodes, Interpretations of electrical behavior. Synth Met 97:151–155
Uludag N, Ates M, Tercan B, Ermis E, Hökelek T (2010) 9-Benzyl-9H-carbazole. Acta Cryst Sect E 66:U94–O17077
Ates M, Uludag N, Sarac AS (2011) Synthesis and electropolymerization of 9-tosyl-9H-carbazole, Electrochemical impedance spectroscopic study and circuit modelling. Fibers Polym 12:8–14
Ates M, Sarac AS (2009) Capacitive behavior of polycarbazole and poly(N-vinylcarbazole)-coated carbon fiber microelectrodes in various solutions. J Appl Electrochem 39(10):2043–2048
Ates M, Uludag N (2013) 6-(3,6-di(thiophene-2-yl)-9H-carbazole-9-yl)-hexanoic acid, alternating copolymer formation, characterization and impedance evaluations. Des Monomers Polym 16(4):398–406
Sun XF, Xu YL, Wang J (2012) Electrpolymerized composite film of polypyrrole and functionalized multi-walled carbon nanotubes: effect of functionalization time on capacitive performance. J Solid State Electrochem 16(5):1781–1789
Mylnikov VS (1994) Photoconducting polymers. Adv Polym Sci 115:1–88
Lee JH, Park JW, Kim SH, Kim HK, Chang YW, Choi SK (1996) Novel polymeric diparhyl derivatives containing a carbazole moiety via palladium-catalyzed polycondensation: synthesis and characterization. J Polym Sci Part A Polym Chem 34:1617–1621
Chen GZ, Shaffer MSP, Coleby D, Dixan G, Zhou WZ, Fray DJ, Windle AH (2000) Carbon nanotube and polypyrrole composites: coating and doping. Adv Mater 12(7):522–526
Ago H, Petritch K, Shaffer MSP, Windle AH, Friend RH (1999) Composites of carbon nanotubes and conjugated polymers for photovoltaic devices. Adv Mater 11(15):1281–1285
Zhang FH, Ni JJ, Yu YJ (2013) High power factor AC-DC Led driver with film capacitors. IEEE Trans Power Electron 28(10):4831–4840
Dhibar S, Sahoo S, Das CK (2013) Fabrication of transition method doped polypyrrole/multiwalled carbon nanotubes nanocomposites for supercapacitor applications. J Appl Polym Sci 130(1):554–562
Liu J, Li M, Zhang YQ, Yang LL, Yao JS (2013) Preparation and enhanced electrochemical properties of Ag/polypyrrole composites electrode materials. J Appl Polym Sci 129(6):3787–3792
Chaudhari S, Sharma Y, Archana PS, Jose R, Ramakrishna S, Mhaisalkar S (2013) Electrospun polyaniline nanofibers web electrodes for supercapacitors. J Appl Polym Sci 129(4):1660–1668
Tran C, Kalra V (2013) Fabrication of porous carbon nanofibers with adjustable pore sizes as electrodes for supercapacitors. J Power Sources 235:289–296
Zhang XT, Zhang J, Liu ZF (2005) Conducting polymer/carbon nanotube composite films made by in situ electropolymerization using an ionic surfactant as the supporting electrolyte. Carbon 43:2186–2191
Fu CP, Zhou HH, Liu R, Huang ZY, Chen JH, Kuang YF (2012) Supercapacitor based on electropolymerized polythiophene and multi-walled carbon nanotubes. Mater Chem Phys 132:596–600
Zhou D, Zhu XL, Zhu J, Yin HS (2005) Influence of the chemical structure of the dithiocarbamates with different N-groups on the reversible addition-fragmentation chain transfer polymerization of styrene. J Polym Sci Part A Polym Chem 43(20):4849–4856
Xue XQ, Zhu JA, Zhang ZB, Cheng ZP, Tu YF, Zhu XL (2010) Synthesis and characterization of azobenzene-functionalized poly(styrene)-b-poly(vinyl acetate) via the combination of RAFT and ‘’click’’ chemistry. Polymer 51:3083–3090
Kundu S, Snyder BER, Walsh AP, Brennessel WW (2013) C=S bond activation of thio ethers using (dippe) Pt (NBE)(2). Polyhedron 58:99–105
Sarac AS, Ates M, Parlak EA (2006) Electrolyte and solvent effects of electrocoated polycarbazole thin films on carbon fiber microelectrode. J Appl Electrochem 36:889–898
Rusling FJ, Suib SL (1994) Characterizing materials with cyclic voltammetry. Adv Mater 6:922–930
Vorotyntsev MA, Daikhin LI, Levi MD (1994) Modeling the impedance properties of electrodes coated with electroactive polymer films. J Electroanal Chem 364(1–2):37–49
Ates M, Uludag N, Sarac AS (2011) Synthesis of 2-(9H-Carbazole-9-yl)ethyl Methacrylate: electrochemical Impedance Spectroscopic Study of Poly(2-(9H-carbazole-9-yl)ethyl methacrylate) on Carbon fiber. J Appl Polym Sci 121:3475–3482
Appetecchi GB, Croce F, Scrosati B (1997) High performance electrolyte membranes for plastic lithium batteries. J Power Sources 66:77–82
Novak P, Muller K, Santharam KSV, Haas O (1997) Electrochemically active polymers for rechargeable batteries. Chem Rev 97(1):207–281
Acknowledgments
This work supported by The Scientific & Technological Council of Turkey (TUBITAK)-TBAG-110T791 Project.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ates, M., Uludag, N. & Arican, F. Synthesis of 9H-carbazole-9-carbothioic methacrylic thioanhydride, electropolymerization, characterization and supercapacitor applications. Polym. Bull. 71, 1557–1573 (2014). https://doi.org/10.1007/s00289-014-1141-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-014-1141-2