3,4-Ethylenedioxythiophenes: methods of construction and postmodification (microreview)
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Dedicated to Professor Vasiliy A. Bakulev on the occasion of his 70th birthday
3,4-Ethylenedioxythiophenes: methods of construction and postmodification (microreview) Elena L. Klimareva1, Grigory V. Zyryanov1,2* 1
Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia; е-mail: [email protected] 2 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg 620108, Russia Submitted April 17, 2020 Accepted May 15, 2020
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1158–1160
This microreview represents approaches to the synthesis of 3,4-ethylenedioxythiophenes, their postmodification, as well as to the synthesis of π-extended analogs of 3,4-ethylenedioxythiophenes and oligomers of the donor-acceptor type. Microreview covers literature from 1997 to 2019.
Introduction Poly(3,4-ethylenedioxythiophene) (PEDOT), one of the most stable and promising conducting polymers (CPs) available, has been employed for chemo/biosensors because of its high electrical conductivity, low band gap, and outstanding environmental stability.1 3,4-Ethylenedioxythiophene (2,3-dihydrothieno[3,4-b][1.4]dioxine, EDOT) is a promising building block for the synthesis of functionally substituted π-conjugated systems (i.e., PEDOT), including copolymers for dual-band and broadly absorbing chromophores with useful photovoltaic and electrochromic properties, as well as for studying the formation factors of
surface nanostructures and nanotubes by the electropolymerization method.2 It can also be used for the synthesis of semiconductor polymers for molecular electronics devices, electrolytic capacitors, electrochromic devices, and antistatic coatings.3 The main disadvantage of EDOT and PEDOT is their low solubility in water and organic solvents.1a Therefore, methods for the transformation of 1,4-dioxane and/or thiophene rings of these compounds have been of great interest. We will consider some ways of modifying the EDOT structure in this microreview.
Construction of the EDOT unit and its postmodification The most common method for constructing the ethylene fragment of EDOT, for example, in compound 3, is to replace the 3,4-dimethoxy group of thiophene 1 with ethylene glycol or glycerol (2) residues with the following cyclization.4
Elena L. Klimareva earned her BSc (Chemical Technology and Biotechnology) and MSc (Chemical Technology and Polymer Chemistry) from the Ural Federal University. At present she is a PhD student at the Ural Federal University under supervision of Professor G. V. Zyryanov. Her research interests are synthetic chemistry, polymer chemistry, and chemistry of materials. 0009-3122/20/56(9)-1158©2020 Springer Science+Business Media, LLC
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Grigory V. Zyryanov, Professor of the Russian Academy of Sciences, earned his PhD (Organic Chemistry) in 2000, and Dr. Sc. (Organic Chemistry) in 2012 from the Ural Federal University. His current research interests in
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