Synthesis and ue of ethylendoxythiophene and its substitutes. (Overview)
DOI:
https://doi.org/10.17072/2223-1838-2020-3-300-317Keywords:
3, 4-ethylenedioxythiophene, EDOT, poly(ethylenedioxythiophene), PEDOT, chromophores, electrochemical polymerizationAbstract
This review presents various synthetic approaches to 3,4-ethylenedioxythiophene (EDOT) and its derivatives. EDOT-based polymer (PEDOT) is one of the most widely used electroconducting high molecular weight heterocyclic compounds and it is often referred as the gold standard of electroconducting p-conjugated polymers. It is well known that embedding of substituents of different nature into the structure of any organic compound affects its properties. Thereby it is of undoubted interest to search new synthetic approaches with an aim to obtain EDOT-based monomers for the further preparation of conducting oligomers, polymers, and copolymers as potential materials for creating organic electronic devices.References
Библиографический список
Guha P. C., Iyer B. H. Attempt towards the synthesis of cantharidin// Journal of Indian Institute of Science. 1938. V.21. P. 115-118.
Turbiez M., Frère P., Allain M., Videlot C., Ackermann J., Roncali J. Design of Organic Semiconductors: Tuning the Electronic Properties of π-Conjugated Oligothiophenes with the 3,4-Ethylenedioxythiophene (EDOT) Building Block. Chemistry// A European Journal. 2005. V.11, № 12. P. 3742–3752.
Cansu Ergun E. G., Eroglu D. An electrochemically and optically stable electrochromic polymer film based on EDOT and 1,2,3,4-tetrahydrophenazine// Organic Electronics, 2019. V. 75. P. 105398.
Liu F., Bai J., Yu G., Ma F., Hou Y., Niu H. Synthesis, electrochromic properties and flash memory behaviors of novel D-A-D polyazomethines containing EDOT and thiophene units// Organic Electronics 2019. P. 105538.
Hayashi S., Yamamoto S., Koizumi T. Effects of molecular weight on the optical and electrochemical properties of EDOT-based π-conjugated polymers// Scientific Reports. 2017. V. 7, № 1.
Hu B., Zhang X., Liu J., Chen X., Zhao J., Jin L. Effects of the redox group of carbazole-EDOT derivatives on their electrochemical and spectroelectrochemical properties// Synthetic Metals. 2017. V. 228. P. 70–78.
Shi J., Zhu X., Xu P., Zhu M., Guo Y., He Y., Meng H. A Redox-Dependent Electrochromic Material:Tetri-EDOT Substituted Thieno[3,2-b]thiophene// Macromolecular Rapid Communications, 2016. V. 37, № 16. P. 1344–1351.
Xue Y., Xue Z., Zhang W., Zhang W., Chen S., Lin K., Xu J. Effects on optoelectronic performances of EDOT end-capped oligomers and electrochromic polymers by varying thienothiophene cores// Journal of Electroanalytical Chemistry. 2019. V. 834. P. 150-160.
Singhal S., Patra A. Benzothiadiazole Bridged EDOT Based Donor-Acceptor Polymer with Tunable Optical, Electrochemical, Morphology and Electrochromic Performance: Effect of Solvent and Electrolyte// Physical Chemistry Chemical Physics. 2020.
Parr Z. S., Rashid R. B., Paulsen B. D., Poggi B., Tan E., Freeley M., Nielsen, C. B. Semiconducting Small Molecules as Active Materials for pType Accumulation Mode Organic Electrochemical Transistors// Advanced Electronic Materials, 2020. P. 2000215.
Groenedaal L., Jonas F., Freitag D., Pielartrzik H., Reynolds J. R. Poly(3,4-ethylenedioxythiophene) and Its Derivatives: Past, Present, and Future// Advanced Materials. 2000. V.12, № 7. P. 481-494.
Das S., Dutta P. K., Panda S., Zade S. S. 3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of C-Si Bond// Journal of Organic Chemistry. 2010. V. 75. P. 4868–4871.
Patent; Nippon Karitto Corporation; Koga, Minekaju; Nishiyama, Masaki; Yisikita, Yoshihito; Kiryu, Toshiyuki; Yamaguchi, Yoji; (23 pag.); KR101558628; (2015); (B1) Korean.
Patent; TOSOH CORPORATION; YANO, HIROKAZU; (11 pg.); JP5663871; (2015); (B2) Japanese
Shimizu M., Hachiya I., Matsumoto T., Inagaki T., Takahashi A. Synthesis of 3,4-Ethylenedioxythiophene (EDOT) from (Z)-But-2-ene-1,4-diol or But-2-yne-1,4-diol// Heterocycles. 2010. V. 82, № 1. P. 449-460.
Shimizu M., Hachiya I., Yamamoto T., Inagaki T., Matsumoto T., Takahashi A., Mizota I. Two-Step Synthesis of 3,4-Ethylenedioxythiophene (EDOT) from 2,3-Butanedione// Heterocycles. 2014.V. 88, №1. P. 607-612.
Wu J. Morphology of Poly(3,4-ethylenedioxythiophene) (PEDOT) Thin Films, Crystals, Cubic Phases, Fibers and Tubes// Material Science. 2011.
Shi W., Zhao T., Xi J., Wang D., Shuai Z. Unravelling Doping Effects on PEDOT at the Molecular Level: From Geometry to Thermoelectric Transport Properties// Journal of the American Chemical Society. 2015. V. 137. P. 12929-12938.
Kumar A., Welsh D. M., Morvant M. C., Piroux F., Abboud K. A., Reynolds J. R. Conducting Poly(3,4-alkylenedioxythiophene) Derivatives as Fast Electrochromics with High-Contrast Ratios// Chemistry of Materials, 1998. V. 10, № 3. P. 896–902.
Zong K., Madridal L., Groendendaal L. B., Reynolds J.R. 3,4-Alkylenedioxy ring formation via double Mitsunobu reaction: an efficient route for the systhesis of 3,4-ethylenedioxythiophene (EDOT) and 3,4-propylenedioxythiophene (ProDOT) derivatives as monomers for electron-rich conducting polymers// Chemical Communications. 2002. V. 21. P. 2498-2499.
Roquet S., Leriche P., Perepichka I., Jousselme B., Levillain E., Frère P., Roncali J. 3,4-Phenylenedioxythiophene (PheDOT): a novel platform for the synthesis of planar substituted π–donor conjugated systems// Journal of Materials Chemistry. 2004. V. 14, № 9. P. 1396–1400.
Ponder J. F., Schmatz B., Hernandez J. L., Reynolds J. R. Soluble phenylenedioxythiophene copolymers via direct (hetero)arylation polymerization: a revived monomer for organic electronics// Journal of Materials Chemistry C. 2018. V. 6, № 5. P. 1064–1070.
Ng S. C., Chan H. S. O., Yu W.-L. Synthesis and characterization of electrically conducting copolymers of ethylenedioxythiophene and 1,3-propylenedioxythiophene with functional substituents// Journal of Materials Science Letters. 1997. V. 16, №10. P. 809–811.
Besbes M., Trippé G., Leviallain E., Mazari M., Le Derf F., Perepichka I. F., Roncali J. Rapid and Efficient Post-Polymerization Functionalization of Poly(3,4-ethylenedioxythiophene) (PEDOT) Derivatives on an Electrode Surface// Advanced Materials. 2001. V. 13, № 16. P. 1249–1252.
Krishnamoorthy K., Kanungo M., Contractor A. Q., Kumar A. Electrochromic polymer based on a rigid cyanobiphenyl substituted 3,4-ethylenedioxythiophene// Synthetic Metals, 2001. V. 124, № 2-3. P. 471–475.
Krishnamoorthy K., Ambade A. V., Mishra S. P., Kanungo M., Contractor A., Kumar A. Dendronized electrochromic polymer based on poly(3,4-ethylenedioxythiophene)// Polymer. 2002. V. 43, № 24. P. 6465–6470.
Zhang L., Wen Y., Yao Y., Duan X., Xu J., Wang X. Electrosynthesis, Characterization, and Application of Poly(3,4-ethylenedioxythiophene) Derivative with a Chloromethyl Functionality// Journal of Applied Polymer Science. 2013. V.130, № 4. P. 39478.
Bu H.-B., Götz G., Reinold E., Vogt A., Schmid, S. Segura J. L., Bäuerle P. Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via “click”-reaction// Tetrahedron. 2011. V. 67, № 6. P. 1114–1125.
Wang Z., Xu J., Lu B., Zhang S., Qin L., Mo D., Zhen S. Poly(thieno[3,4-b]-1,4-oxathiane): Medium Effect on Electropolymerization and Electrochromic Performance// Langmuir. 2014. V. 30, № 51. P. 15581–15589.
. Darmanin T., Laugier J.-P., Orange F., Guittard F. Influence of the monomer structure and electrochemical parameters on the formation of nanotubes with parahydrophobic properties (high water adhesion) by a templateless electropolymerization process// Journal of Colloid and Interface Science. 2016. V. 466. P. 413–424.
Blanchard P., Cappon A., Levillain E., Nicolas Y., Frère P., Roncali, J. Thieno[3,4-b]-1,4-oxathiane: An Unsymmetrical Sulfur Analogue of 3,4-Ethylenedioxythiophene (EDOT) as a Building Block for Linear π-Conjugated Systems// Organic Letters. 2002. V. 4, №4. P. 607–609.
Li M., Sheynin Y., Patra A., Bendikov M. Tuning the Electrochromic Properties of Poly(alkyl-3,4-ethylenedioxyselenophenes) Having High Contrast Ratio and Coloration Efficiency// Chemistry of Materials. 2009.V. 21, № 12. P. 2482–2488.
Wijsboom Y. H., Patra A., Zade S. S., Sheynin Y., Li M., Shimon L. J. W., Bendikov M. Controlling Rigidity and Planarity in Conjugated Polymers: Poly(3,4-ethylenedithioselenophene)// Angewandte Chemie, 2009. V. 121, № 30. P. 5551–5555.
Modarresi M., Mehandzhiyski A., Fahlman M., Tybrandt K., Zozoulenko I. Microscopic Understanding of the Granular Structure and the Swelling of PEDOT:PSS// Macromolecules. 2020. V. 53. P. 6267−6278.
References
Guha, P. C. and Iyer, B. H. (1938), “Attempt towards the synthesis of cantharidin”, Journal of Indian Institute of Science. Vol.21. pp. 115-118.
Turbiez, M., Frère, P., Allain, M., Videlot, C., Ackermann, J. and Roncali, J. (2005), “Design of Organic Semiconductors: Tuning the Electronic Properties of π-Conjugated Oligothiophenes with the 3,4-Ethylenedioxythiophene (EDOT) Building Block. Chemistry”, A European Journal. Vol.11, no 12. pp. 3742–3752.
Cansu Ergun, E. G. and Eroglu, D. (2019), “An electrochemically and optically stable electrochromic polymer film based on EDOT and 1,2,3,4-tetrahydrophenazine”, Organic Electronics. Vol. 75. pp. 105398.
Liu, F., Bai, J., Yu, G., Ma, F., Hou, Y. and Niu, H. (2019), “Synthesis, electrochromic properties and flash memory behaviors of novel D-A-D polyazomethines containing EDOT and thiophene units”, Organic Electronics. Vol. 77. pp. 105538.
Hayashi, S., Yamamoto, S. and Koizumi, T. (2017), “Effects of molecular weight on the optical and electrochemical properties of EDOT-based π-conjugated polymers”, Scientific Reports. Vol. 7, no 1. pp. 1078.
Hu, B., Zhang, X., Liu, J., Chen, X., Zhao, J. and Jin, L. (2017), “Effects of the redox group of carbazole-EDOT derivatives on their electrochemical and spectroelectrochemical propertie”, Synthetic Metals. Vol. 228, pp. 70–78.
Shi, J., Zhu, X., Xu, P., Zhu, M., Guo, Y., He, Y. and Meng, H. (2016), “A Redox-Dependent Electrochromic Material:Tetri-EDOT Substituted Thieno[3,2-b]thiophene”, Macromolecular Rapid Communications. Vol. 37, no 16. pp. 1344–1351.
Xue, Y., Xue, Z., Zhang, W., Zhang, W., Chen, S., Lin, K. and Xu, J. (2019), “Effects on optoelectronic performances of EDOT end-capped oligomers and electrochromic polymers by varying thienothiophene cores”, Journal of Electroanalytical Chemistry. Vol. 834, pp. 150-160.
Singhal, S. and Patra, A. (2020) “Benzothiadiazole Bridged EDOT Based Donor-Acceptor Polymer with Tunable Optical, Electrochemical, Morphology and Electrochromic Performance: Effect of Solvent and Electrolyte”, Physical Chemistry Chemical Physics. Vol.22, pp.14527-14536.
Parr, Z. S., Rashid, R. B., Paulsen, B. D., Poggi, B., Tan, E., Freeley, M. and Nielsen, C. B. (2020), “Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors”, Advanced Electronic Material., pp. 2000215.
Groenedaal, L., Jonas, F., Freitag, D., Pielartrzik, H. and Reynolds, J. R. (2000), “Poly(3,4-ethylenedioxythiophene) and Its Derivatives: Past, Present, and Future”, Advanced Materials. Vol.12, no 7. pp. 481-494.
Das S., Dutta P. K., Panda S. and Zade S. S. (2010), “3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of C-Si Bond”, Journal of Organic Chemistry. Vol. 75, pp. 4868–4871.
Patent; Nippon Karitto Corporation; Koga, Minekaju; Nishiyama, Masaki; Yisikita, Yoshihito; Kiryu, Toshiyuki; Yamaguchi, Yoji; (23 pag.); KR101558628; (2015); (B1) Korean.
Patent; TOSOH CORPORATION; YANO, HIROKAZU; (11 pg.); JP5663871; (2015); (B2) Japanese
Shimizu, M., Hachiya, I., Matsumoto, T., Inagaki, T. and Takahashi, A. (2010), “Synthesis of 3,4-Ethylenedioxythiophene (EDOT) from (Z)-But-2-ene-1,4-diol or But-2-yne-1,4-diol”, Heterocycles. Vol. 82, no 1. pp. 449-460.
Shimizu, M., Hachiya, I., Yamamoto, T., Inagaki, T., Matsumoto, T., Takahashi, A. and Mizota, I. (2014), “Two-Step Synthesis of 3,4-Ethylenedioxythiophene (EDOT) from 2,3-Butanedione”, Heterocycles. Vol. 88, no 1. pp. 607-612.
Wu, J. (2011), “Morphology of Poly(3,4-ethylenedioxythiophene) (PEDOT) Thin Films, Crystals, Cubic Phases, Fibers and Tubes”, Material Science.
Shi, W., Zhao, T., Xi, J., Wang, D. and Shuai, Z. (2015), “Unravelling Doping Effects on PEDOT at the Molecular Level: From Geometry to Thermoelectric Transport Properties” Journal of the American Chemical Society, Vol. 137, pp. 12929-12938.
Kumar, A., Welsh, D. M., Morvant, M. C., Piroux, F., Abboud, K. A. and Reynolds, J. R. (1998), “Conducting Poly(3,4-alkylenedioxythiophene) Derivatives as Fast Electrochromics with High-Contrast Ratios”, Chemistry of Materials. Vol. 10, no 3. pp. 896–902.
Zong K., Madridal L., Groendendaal L. B. and Reynolds J. (2002), “3,4-Alkylenedioxy ring formation via double Mitsunobu reaction: an efficient route for the synthesis of 3,4-ethylenedioxythiophene (EDOT) and 3,4-propylenedioxythiophene (ProDOT) derivatives as monomers for electron-rich conducting polymers”, Chemical Communications. Vol. 21, pp. 2498-2499.
Roquet, S., Leriche, P., Perepichka, I., Jousselme, B., Levillain, E., Frère, P. and Roncali, J. (2004), “3,4-Phenylenedioxythiophene (PheDOT): a novel platform for the synthesis of planar substituted π–donor conjugated systems”, Journal of Materials Chemistry. Vol. 14, no 9. pp. 1396–1400.
Ponder, J. F., Schmatz, B., Hernandez, J. L. and Reynolds, J. R. (2018), “Soluble phenylenedioxythiophene copolymers via direct (hetero)arylation polymerization: a revived monomer for organic electronics”, Journal of Materials Chemistry C. Vol. 6, no 5. pp. 1064–1070.
Ng, S. C., Chan, H. S. O. and Yu, W.-L. (1997), “Synthesis and characterization of electrically conducting copolymers of ethylenedioxythiophene and 1,3-propylenedioxythiophene with functional substituents”, Journal of Materials Science Letters. Vol. 16, no 10. pp. 809–811.
Besbes, M., Trippé, G., Leviallain, E., Mazari, M., Le Derf, F., Perepichka, I. F. and Roncali, J. (2001), “Rapid and Efficient Post-Polymerization Functionalization of Poly(3,4-ethylenedioxythiophene) (PEDOT) Derivatives on an Electrode Surface”, Advanced Materials. Vol. 13, no 16. pp. 1249–1252.
Krishnamoorthy, K., Kanungo, M., Contractor, A. Q. and Kumar, A. (2001), “Electrochromic polymer based on a rigid cyanobiphenyl substituted 3,4-ethylenedioxythiophene”, Synthetic Metals. Vol. 124, no 2-3. pp. 471–475.
Krishnamoorthy, K., Ambade, A. V., Mishra, S. P., Kanungo, M., Contractor, A. and Kumar, A. (2002), “Dendronized electrochromic polymer based on poly(3,4-ethylenedioxythiophene)”, Polymer. Vol. 43, no 24. pp. 6465–6470.
Zhang, L., Wen, Y., Yao, Y., Duan, X., Xu, J. and Wang, X. (2013), “Electrosynthesis, Characterization, and Application of Poly(3,4-ethylenedioxythiophene) Derivative with a Chloromethyl Functionality”, Journal of Applied Polymer Science, Vol. 130, no 4. pp. 39478.
Bu, H.-B., Götz, G., Reinold, E., Vogt, A., Schmid, S., Segura, J. L. and Bäuerle, P. (2011), “Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via “click”-reaction”, Tetrahedron. Vol. 67, no 6. pp. 1114–1125.
Wang, Z., Xu, J., Lu, B., Zhang, S., Qin, L., Mo, D., and Zhen, S. (2014), “Poly(thieno[3,4-b]-1,4-oxathiane): Medium Effect on Electropolymerization and Electrochromic Performance”, Langmuir. Vol. 30, no 51. pp. 15581–15589.
. Darmanin, T., Laugier, J.-P., Orange, F. and Guittard, F. (2016), “Influence of the monomer structure and electrochemical parameters on the formation of nanotubes with parahydrophobic properties (high water adhesion) by a templateless electropolymerization process”, Journal of Colloid and Interface Science. Vol. 466, pp. 413–424.
Blanchard, P., Cappon, A., Levillain, E., Nicolas, Y., Frère, P. and Roncali, J. (2002), “Thieno[3,4-b]-1,4-oxathiane: An Unsymmetrical Sulfur Analogue of 3,4-Ethylenedioxythiophene (EDOT) as a Building Block for Linear π-Conjugated Systems”, Organic Letters. Vol. 4, no 4. pp. 607–609.
Li, M., Sheynin, Y., Patra, A. and Bendikov, M. (2009), “Tuning the Electrochromic Properties of Poly(alkyl-3,4-ethylenedioxyselenophenes) Having High Contrast Ratio and Coloration Efficiency”, Chemistry of Materials. Vol. 21, no 12. pp. 2482–2488.
Wijsboom, Y. H., Patra, A., Zade, S. S., Sheynin, Y., Li, M., Shimon, L. J. W. and Bendikov, M. (2009), “Controlling Rigidity and Planarity in Conjugated Polymers: Poly(3,4-ethylenedithioselenophene)”, Angewandte Chemie. Vol. 121, no 30. pp. 5551–5555.
Modarresi, M., Mehandzhiyski, A., Fahlman, M., Tybrandt, K. and Zozoulenko, I. (2020), “Microscopic Understanding of the Granular Structure and the Swelling of PEDOT:PSS”, Macromolecules. Vol. 53, pp. 6267−6278.
