Synthesis and characterization of poly(S-2-mercaptoethyl 2-(thiophen-3-yl)ethanethioate) by electrochemical polymerization
Nguyen, Ha Tran; Nguyen, Le-Thu Thi
http://dx.doi.org/10.1590/0104-1428.2208
Polímeros: Ciência e Tecnologia, vol.25, n5, p.503-507, 2015
Abstract
A novel monomer of S-2-mercaptoethyl 2-(thiophen-3-yl)ethanethioate (MTE) were synthesized via esterification reaction between 2-(thiophen-3-yl)acetic and ethane-1,2-dithiol in the presence of dicyclohexyl-carbodiimide (DCC) and N,N’-dimethylpyridin-4-amine (4-DMAP) as catalytic system. The structure of monomer was characterized via MS, 1H-NMR and 13C-NMR spectroscopies. The electrochemical polymerization of MTE monomer was performed in acetonitrile using lithium perchlorate (LiClO4) as electrolyte agent. The obtained polymer film (PMTE) was characterized via cyclic voltammetry and it exhibited the main oxidation peaks centered at +2V.
Keywords
polythiophene, electrochemical polymerization, cyclic voltammograms.
References
1. McCullough, R. D., Tristram-Nagle, S., Williams, S. P., Lowe, R. D., & Jayaraman, M. (1993). Self-orienting head-to-tail poly(3-alkylthiophenes): new insights on structure-property relationships in conducting polymers. Journal of the American Chemical Society, 115(11), 4910-4911. http://dx.doi.org/10.1021/ja00064a070.
2. Chen, T. A., Wu, X., & Rieke, R. D. (1995). Regiocontrolled synthesis of Poly(3-alkylthiophenes) mediated by rieke zinc: their characterization and solid-state properties. Journal of the American Chemical Society, 117(1), 233-244. http://dx.doi.org/10.1021/ja00106a027.
3. Bao, Z., Dodabalapur, A., & Lovinger, A. J. (1996). Soluble and processable regioregular poly(3-hexylthiophene) for thin film field-effect transistor applications with high mobility. Applied Physics Letters, 69(26), 4108-4110. http://dx.doi.org/10.1063/1.117834.
4. Greene, R. L., Street, G. B., & Suter, L. J. (1975). Superconductivity in polysulfur nitride (SN)x. Physical Review Letters, 34(10), 577-579. http://dx.doi.org/10.1103/PhysRevLett.34.577.
5. MacDiarmid, A. G. (2001). Nobel lecture: “synthetic metals”: a novel role for organic polymers. Reviews of Modern Physics, 73(3), 701-712. http://dx.doi.org/10.1103/RevModPhys.73.701. PMid:11458347.
6. Roncali, J. (1992). Conjugated poly(thiophenes): synthesis, functionalization, and application. Chemical Reviews, 92(4), 711-738. http://dx.doi.org/10.1021/cr00012a009.
7. Yu, G., Wang, J., McElvain, J., & Heeger, A. J. (1998). Large-area, full-color image sensors made with semiconducting polymers. Advanced Materials, 10(17), 1431-1434. http://dx.doi.org/10.1002/(SICI)1521-4095(199812)10:17<1431::AID-ADMA1431>3.0.CO;2-4.
8. Welzel, H. P., Kossmehl, G., Schneider, J., & Plieth, W. (1995). Reactive groups on polymer-covered electrodes. 2. functionalized thiophene polymers by electrochemical polymerization and their application as polymeric reagents. Macromolecules, 28(16), 5575-5580. http://dx.doi.org/10.1021/ma00120a023.
9. Tsumura, A., Koezuka, H., & Ando, T. (1986). Macromolecular electronic device: field-effect transistor with a polythiophene thin film. Applied Physics Letters, 49(18), 1210-1212. http://dx.doi.org/10.1063/1.97417.
10. Argun, A. A., Cirpan, C., & Reynolds, J. R. (2003). The first truly all-polymer electrochromic devices. Advanced Materials, 10(16), 1338-1341. http://dx.doi.org/10.1002/adma.200305038.
11. Huynh, W. U., Dittmer, J. J., & Alivisatos, A. P. (2002). Hybrid nanorod-polymer solar cells. Science, 295(5564), 2425-2427. http://dx.doi.org/10.1126/science.1069156. PMid:11923531.
12. Arias, A. C., MacKenzie, J. D., McCulloch, I., Rivnay, J., & Salleo, A. (2010). Materials and applications for large area electronics: solution-based approaches. Chemical Reviews, 110(1), 3-24. http://dx.doi.org/10.1021/cr900150b. PMid:20070114.
13. Ertas, M., Cırpan, A., & Toppare, L. (2004). Synthesis and characterization of conducting copolymers of succinic acid bis-(4-pyrrol-1-yl-phenyl) ester and their electrochromic properties. Synthetic Metals, 143(1), 49-58. http://dx.doi.org/10.1016/j.synthmet.2003.10.018.
14. Pang, Y., Li, X., Ding, H., Shi, G., & Jin, L. (2007). Electropolymerization of high quality electrochromic poly(3-alkyl-thiophene)s via a room temperature ionic liquid. Electrochimica Acta, 52(20), 6172-6177. http://dx.doi.org/10.1016/j.electacta.2007.04.015.
15. Groenendaal, L., Jonas, F., Freitag, D., Pielartzik, H., & Reynolds, J. R. (2000). Poly(3,4-ethylenedioxythiophene) and its derivatives: past, present, and future. Advanced Materials, 12(7), 481-494. http://dx.doi.org/10.1002/(SICI)1521-4095(200004)12:7<481::AID-ADMA481>3.0.CO;2-C.
16. Novak, J. P., Brousseau, L. C., Vance, F. W., Johnson, R. C., Lemon, B. I., Hupp, J. T., & Feldheim, D. L. (2000). Nonlinear optical properties of molecularly bridged gold nanoparticle arrays. Journal of the American Chemical Society, 122(48), 12029-12030. http://dx.doi.org/10.1021/ja003129h.
17. Vericat, C., Vela, M. E., Benitez, G., Carro, P., & Salvarezza, R. C. (2010). Self-assembled monolayers of thiols and dithiols on gold: new challenges for a well-known system. Chemical Society Reviews, 39(5), 1805-1834. http://dx.doi.org/10.1039/b907301a. PMid:20419220.
18. Nakamura, T., Kondoh, H., Matsumoto, M., & Nozoye, H. (1999). Recognition properties of the nano-ordered structures of bis(mercaptomethyl)terthiophene monolayers on Au (111). Synthetic Metals, 103(1-3), 2143-2144. http://dx.doi.org/10.1016/S0379-6779(98)00602-X.
19. Muglali, M. I., Erbe, A., Chen, Y., Barth, C., Koelsch, P., & Rohwerder, M. (2013). Modulation of electrochemical hydrogen evolution rate by araliphatic thiol monolayers on gold. Electrochimica Acta, 90, 17-26. http://dx.doi.org/10.1016/j.electacta.2012.11.116. PMid:24235778.
20. Civit, L., Fragoso, A., & O’Sullivan, C. K. (2010). Thermal stability of diazonium derived and thiol-derived layers on gold for application in genosensors. Electrochemistry Communications, 12(8), 1045-1048. http://dx.doi.org/10.1016/j.elecom.2010.05.020.
2. Chen, T. A., Wu, X., & Rieke, R. D. (1995). Regiocontrolled synthesis of Poly(3-alkylthiophenes) mediated by rieke zinc: their characterization and solid-state properties. Journal of the American Chemical Society, 117(1), 233-244. http://dx.doi.org/10.1021/ja00106a027.
3. Bao, Z., Dodabalapur, A., & Lovinger, A. J. (1996). Soluble and processable regioregular poly(3-hexylthiophene) for thin film field-effect transistor applications with high mobility. Applied Physics Letters, 69(26), 4108-4110. http://dx.doi.org/10.1063/1.117834.
4. Greene, R. L., Street, G. B., & Suter, L. J. (1975). Superconductivity in polysulfur nitride (SN)x. Physical Review Letters, 34(10), 577-579. http://dx.doi.org/10.1103/PhysRevLett.34.577.
5. MacDiarmid, A. G. (2001). Nobel lecture: “synthetic metals”: a novel role for organic polymers. Reviews of Modern Physics, 73(3), 701-712. http://dx.doi.org/10.1103/RevModPhys.73.701. PMid:11458347.
6. Roncali, J. (1992). Conjugated poly(thiophenes): synthesis, functionalization, and application. Chemical Reviews, 92(4), 711-738. http://dx.doi.org/10.1021/cr00012a009.
7. Yu, G., Wang, J., McElvain, J., & Heeger, A. J. (1998). Large-area, full-color image sensors made with semiconducting polymers. Advanced Materials, 10(17), 1431-1434. http://dx.doi.org/10.1002/(SICI)1521-4095(199812)10:17<1431::AID-ADMA1431>3.0.CO;2-4.
8. Welzel, H. P., Kossmehl, G., Schneider, J., & Plieth, W. (1995). Reactive groups on polymer-covered electrodes. 2. functionalized thiophene polymers by electrochemical polymerization and their application as polymeric reagents. Macromolecules, 28(16), 5575-5580. http://dx.doi.org/10.1021/ma00120a023.
9. Tsumura, A., Koezuka, H., & Ando, T. (1986). Macromolecular electronic device: field-effect transistor with a polythiophene thin film. Applied Physics Letters, 49(18), 1210-1212. http://dx.doi.org/10.1063/1.97417.
10. Argun, A. A., Cirpan, C., & Reynolds, J. R. (2003). The first truly all-polymer electrochromic devices. Advanced Materials, 10(16), 1338-1341. http://dx.doi.org/10.1002/adma.200305038.
11. Huynh, W. U., Dittmer, J. J., & Alivisatos, A. P. (2002). Hybrid nanorod-polymer solar cells. Science, 295(5564), 2425-2427. http://dx.doi.org/10.1126/science.1069156. PMid:11923531.
12. Arias, A. C., MacKenzie, J. D., McCulloch, I., Rivnay, J., & Salleo, A. (2010). Materials and applications for large area electronics: solution-based approaches. Chemical Reviews, 110(1), 3-24. http://dx.doi.org/10.1021/cr900150b. PMid:20070114.
13. Ertas, M., Cırpan, A., & Toppare, L. (2004). Synthesis and characterization of conducting copolymers of succinic acid bis-(4-pyrrol-1-yl-phenyl) ester and their electrochromic properties. Synthetic Metals, 143(1), 49-58. http://dx.doi.org/10.1016/j.synthmet.2003.10.018.
14. Pang, Y., Li, X., Ding, H., Shi, G., & Jin, L. (2007). Electropolymerization of high quality electrochromic poly(3-alkyl-thiophene)s via a room temperature ionic liquid. Electrochimica Acta, 52(20), 6172-6177. http://dx.doi.org/10.1016/j.electacta.2007.04.015.
15. Groenendaal, L., Jonas, F., Freitag, D., Pielartzik, H., & Reynolds, J. R. (2000). Poly(3,4-ethylenedioxythiophene) and its derivatives: past, present, and future. Advanced Materials, 12(7), 481-494. http://dx.doi.org/10.1002/(SICI)1521-4095(200004)12:7<481::AID-ADMA481>3.0.CO;2-C.
16. Novak, J. P., Brousseau, L. C., Vance, F. W., Johnson, R. C., Lemon, B. I., Hupp, J. T., & Feldheim, D. L. (2000). Nonlinear optical properties of molecularly bridged gold nanoparticle arrays. Journal of the American Chemical Society, 122(48), 12029-12030. http://dx.doi.org/10.1021/ja003129h.
17. Vericat, C., Vela, M. E., Benitez, G., Carro, P., & Salvarezza, R. C. (2010). Self-assembled monolayers of thiols and dithiols on gold: new challenges for a well-known system. Chemical Society Reviews, 39(5), 1805-1834. http://dx.doi.org/10.1039/b907301a. PMid:20419220.
18. Nakamura, T., Kondoh, H., Matsumoto, M., & Nozoye, H. (1999). Recognition properties of the nano-ordered structures of bis(mercaptomethyl)terthiophene monolayers on Au (111). Synthetic Metals, 103(1-3), 2143-2144. http://dx.doi.org/10.1016/S0379-6779(98)00602-X.
19. Muglali, M. I., Erbe, A., Chen, Y., Barth, C., Koelsch, P., & Rohwerder, M. (2013). Modulation of electrochemical hydrogen evolution rate by araliphatic thiol monolayers on gold. Electrochimica Acta, 90, 17-26. http://dx.doi.org/10.1016/j.electacta.2012.11.116. PMid:24235778.
20. Civit, L., Fragoso, A., & O’Sullivan, C. K. (2010). Thermal stability of diazonium derived and thiol-derived layers on gold for application in genosensors. Electrochemistry Communications, 12(8), 1045-1048. http://dx.doi.org/10.1016/j.elecom.2010.05.020.
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