3, 4-ethylenedioxythiophene EDOT

The prepolymer 3,4-ethylenedioxythiophene (EDOT) has been made in good yield from a pair of diols (Equation 15) <2002CC2690>. 

Turbiez, M., Frere, P., Blanchard, P., and Roncali, J., Mixed 7t-conjugated oligomers of thiophene and 3,4-ethylenedioxythiophene (EDOT), Tetrahedron Lett., 41, 5521, 2000. 

In a practical and simple synthesis of the valuable 3,4-ethylenedioxythiophene (EDOT) 7, 2,3-dimethoxy-l,3-butadiene 8 underwent transformation to 3,4-dimethoxythiophene 9 upon treatment with sulfur dichloride. Displacement of the methoxy groups with ethylene glycol in the presence of an acid catalyst finally gave the desired compound 7 <04TL6049>. 

The heterocyclic monomers, i.e., pyrrole, aniline and 3, 4-ethylenedioxythiophene (EDOT], with oxidation potentials lower than that of water decomposition can be electrochemically polymerized in aqueous media. However, the solubility of aromatic... 

Caras-Quintero, D., and P. Bauerle. 2004. Synthesis of the first enantiomerically pure and chiral, disubstituted 3,4-ethylenedioxythiophenes (EDOTs) and corresponding stereo- and regioregular PEDOTs. Chem Commun 8 926-927. 

Seshadri, V., L. Wu, and G.A. Sotzing. 2003. Gonjugated polymers via electrochemical polymerization of thieno[3,4-1 ]thiophene (T34bT) and 3,4-ethylenedioxythiophene (EDOT). Langmuir 19 9479. 

Sotzing, G.A., J.L. Reddinger, and J.R. Reynolds. 1997. Redox active electochromic polymers from low oxidation monomers containing 3,4-ethylenedioxythiophene (EDOT). Synth Met 84 199. 

Roncali, J., P. Blanchard, and P. Frere. 2005. 3,4-Ethylenedioxythiophene (EDOT) as a versatile building block for avdanced functional ir-conjugated systems. J Mater Chem 15 1589—1610. Chang, A.-C., R.L. Blankespoor, and L.L. Miller. 1987. Characterization and spectroelectrochemical studies of soluble polymerized 3-methoxythiophene. J Electroanal Chem 236 239-252. 

Blanchard, R, A. Cappon, E. Levillain, Y. Nicolas, P. Frere, and J. Roncali. 2002. Thieno[3,4-b]-l,4-oxathiane An unsymmetrical sulfur analogue of 3,4-ethylenedioxythiophene (EDOT) as a building block for linear pi-conjugated systems. Org Lett 4 607-609. 

Segura, J.L., R. Gomez, E. Reinold, and P. Bauerle. 2005. Synthesis and electropolymerization of a perylenebisimide-functionalized 3,4-ethylenedioxythiophene (EDOT) derivative. Org Lett 7 2345-2348. 

Three-layered nanoparticles containing an hbPG core and cross-linked block copolymers based on N-isopropyl acrylate and N,N-dimethylaminoethyl acrylate as the respective arms were synthesized and proved to be thermoresponsive. ° Chu and co-workers" reported electrically conductive core-shell nanoparticles based on poly(n-butylacrylate-b-polystyrene) multiarm star polymers. The PS segments were converted to poly(p-styrenesulfonate) (PSS), thus generating amphiphilic tmimolecular micelles. Then the oxidative propagation of 3,4-ethylenedioxythiophene (EDOT) on the PSS chains was carried out by counterion-induced polymerization to produce a stable aqueous dispersion of the respective PEDOT complex. 

While a lot of literatures concerning conducting polymer nanoparticle were published, there were limited reports on the fabrication of PEDOT nanoparticle due to the relatively low solubility of the 3,4-ethylenedioxythiophene (EDOT) monomer in aqueous media. Several synthetic methods for the PEDOT nanoparticle have been reported using seed polymerization, emulsion polymerization and dispersion polymerization. 

I. F. Perepichka, E. LevUlain and J. Roncah, Effect of substitution of 3,4-ethylenedioxythiophene (EDOT) on the electronic properties of the derived electrogenerated low handgap conjugated polymers, J. Mater. Chem., 14, 1679-1681 (2004). 

Double substitution of the two -positions of one thiophene ring was also considered for the electrosynthesis of corresponding polymers [10]. In this context, the development of 3,4-ethylenedioxythiophene (EDOT) represented a breakthrough for the optimization of the electrochemical polymerization of thiophene-based n-conjugated systems. 

After the initial work of Jonas and co-workers at the Bayer research laboratories [59], the last decade has witnessed the emergence of 3,4-ethylenedioxythiophene (EDOT) at the forefront of the chemistry of linear K-conjugated systems (Scheme 9.10) [60-62]. 

Early progress in polythiophene chemistry was achieved by the synthesis of mono- and dialkoxy-substituted thiophene derivatives developed by Leclerc s group [6], industrial scientists at Hoechst [7-9] and Japanese researchers [10, 11], However, most polymers of mono- and dialkoxythiophenes exhibited low conductivity in the oxidized, doped state. A breakthrough in this area was the synthesis of polymers of the bicyclic 3,4-ethylenedioxythiophene (EDOT) and its derivatives - electrochemically polymerized by Heinze and co-workers and chemically polymerized by Heywang and Jonas of the Bayer Corporate Research Laboratories [12, 13]. In contrast to the non-bicyclic polymers of mono- and dialkoxythiophenes, poly-3,4-ethylenedioxythiophene (PEDOT) has a very stable and highly conductive cationic doped state. The low HOMO-LUMO bandgap of conductive PEDOT [14] allowed the formation of a tremendously stable, highly conductive ICP. Technical use and commercialization quickly followed today, ICPs based on PEDOT are commercially available in multi-ton quantities. 

K. Zong, L. Madrigal, L. Groenendaal and J. R. Reynolds, 3,4-Alkylenedioxy ring formation via double Mitsunobu reactions an efficient route for the synthesis of 3,4-ethylenedioxythiophene (EDOT) and... 

D. Caras-Quintero and P. BSuerle, Efficient synthesis of 3,4-ethylenedioxythiophenes (EDOT) by Mitsunobu reaction, Chem. Commun. 2690-2691 (2002). 

F. von Kieseritzky, F. Allared, E. Dahlstedt and J. Hellberg, Simple one-step synthesis of 3,4-dimethoxythiophene and its conversion into 3,4-ethylenedioxythiophene (EDOT), Tetrahedron Lett. 45, 6049-6050 (2004). 

Turbiez et al. synthesized a series of co-oligomers of thiophene and 3,4-ethylenedioxythiophene (EDOT) ranging from four to seven rings [72a]. They found that alternating thiophene and EDOT units leads to... 

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