211235-87-9Relevant articles and documents
Effect of 3,4-ethylenedioxy-extension of thiophene core on the DNA/RNA binding properties and biological activity of bisbenzimidazole amidines
Stolic, Ivana,Miskovic, Katarina,Magdaleno, Anahi,Silber, Ariel Mariano,Piantanida, Ivo,Bajic, Miroslav,Glavas-Obrovac, Ljubica
, p. 2544 - 2554 (2009)
Novel bisbenzimidazoles (4-6), characterized by 3,4-ethylenedioxy-extension of thiophene core, revealed pronounced affinity and strong thermal stabilization effect toward ds-DNA. They interact within ds-DNA grooves as dimmers or even oligomers and agglome
Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction
Al-jumaili, Mustafa A-jabbar,Woodward, Simon
, p. 5847 - 5852 (2017)
Derivatives of 3,4-ethylenedithiothiophene (EDTT) are reported starting from tetrabromothiophene. Selective 2,5-dilithiation followed by reaction with a range of aldehydes gives diols as mixtures of diastereomers. Only the 2 and 5 positions in thiophene react leaving the 3,4-bromides for further elaboration. The diols are oxidised to their corresponding diketones using activated MnO2. Reaction with 1,2-ethanedithiol, by addition-elimination, provides access to novel monomers for the preparation of conjugated copolymers of 3,4-ethylenedithiothiophene (EDTT). A range of these monomers can be attained by applying the synthesis of a series of ketones applicable to further synthesis of π-extended thiophene-based organic semiconductors. Finally, this new route was compared to 3,4-ethylenedioxythiophene (EDOT) dialdehyde derivatives synthesised by an alternative to literature chemistry.
Synthesis and Optical Properties of New Chalcones Containing a 3,4-Ethylenedioxythiophene Fragment
Ignashevich,Shavrina,Shklyaeva,Abashev
, p. 1920 - 1928 (2021/01/13)
Abstract: A new series of chalcones bearing two or more 3,4-ethylenedioxythiophene fragments were synthesized, and their optical properties were studied. The Stokes shifts (Δλ) and band gaps (Egopt) were calculated on the basis of the absorption and emission spectra. The largest Stokes shift (115 nm) was found for a symmetrical product of the terephthalaldehyde and 3,4-ethylenedioxythiophene-2-carbaldehyde condensation, and the smallest band gap (1.93 eV) is characteristic of a chalcone that contains a 2,2',5',2''-ter(3,4-ethylenedioxythiophene). Correlations were established between the band gap and mutual arrangement of the 3,4-ethylenedioxythiophene fragments in the prepared chalcones.
Azatruxene-Based, Dumbbell-Shaped, Donor–π-Bridge–Donor Hole-Transporting Materials for Perovskite Solar Cells
Illicachi, Luis A.,Urieta-Mora, Javier,Calbo, Joaquín,Aragó, Juan,Igci, Cansu,García-Benito, Inés,Momblona, Cristina,Insuasty, Braulio,Ortiz, Alejandro,Roldán-Carmona, Cristina,Molina-Ontoria, Agustín,Ortí, Enrique,Martín, Nazario,Nazeeruddin, Mohammad Khaja
supporting information, p. 11039 - 11047 (2020/08/03)
Three novel donor–π-bridge–donor (D-π-D) hole-transporting materials (HTMs) featuring triazatruxene electron-donating units bridged by different 3,4-ethylenedioxythiophene (EDOT) π-conjugated linkers have been synthesized, characterized, and implemented in mesoporous perovskite solar cells (PSCs). The optoelectronic properties of the new dumbbell-shaped derivatives (DTTXs) are highly influenced by the chemical structure of the EDOT-based linker. Red-shifted absorption and emission and a stronger donor ability were observed in passing from DTTX-1 to DTTX-2 due to the extended π-conjugation. DTTX-3 featured an intramolecular charge transfer between the external triazatruxene units and the azomethine–EDOT central scaffold, resulting in a more pronounced redshift. The three new derivatives have been tested in combination with the state-of-the-art triple-cation perovskite [(FAPbI3)0.87(MAPbBr3)0.13]0.92[CsPbI3]0.08 in standard mesoporous PSCs. Remarkable power conversion efficiencies of 17.48 percent and 18.30 percent were measured for DTTX-1 and DTTX-2, respectively, close to that measured for the benchmarking HTM spiro-OMeTAD (18.92 percent), under 100 mA cm?2 AM 1.5G solar illumination. PSCs with DTTX-3 reached a PCE value of 12.68 percent, which is attributed to the poorer film formation in comparison to DTTX-1 and DTTX-2. These PCE values are in perfect agreement with the conductivity and hole mobility values determined for the new compounds and spiro-OMeTAD. Steady-state photoluminescence further confirmed the potential of DTTX-1 and DTTX-2 for hole-transport applications as an alternative to spiro-OMeTAD.
Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation
Bao, Yan,Wang, Jian-Yong,Zhang, Ya-Xuan,Li, Yan,Wang, Xi-Sheng
supporting information, p. 3147 - 3150 (2018/07/13)
A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.
Synthesis and mesomorphic properties of novel Schiff base liquid crystalline EDOT derivatives
Gowda, Ashwathanarayana,Roy, Arun,Kumar, Sandeep
, p. 840 - 847 (2016/12/30)
Herein, we reported novel banana liquid crystals derived from ethylenedioxythiophene (EDOT) central unit encompass with Schiff base. Structural charecterization of these compounds was carried out from their spectral and elemental analysis. Physical properties of all the newly synthesized compounds were investigated by polarising optical microscopy, differential scanning calorimetry, thermogravimetric analysis, X-ray diffraction and Raman spectroscopy. EDOT bearing three-ring Schiff base bent-core compounds are non-mesomorphic but all the Schiff bases containing five-rings exhibit enantiotropic mesophase behaviour. The higher homologues show long range nematic phase along with a smectic C phase at lower temperature. While the lower homologues exhibit only N phase. The bent-angle in these compounds is in between of calamitic LCs and banana LCs; therefore, the molecules escape from the polar order packing observed in typical bent core LCs. Detailed XRD investigation endorses the presence of the N phase in lower homologues and Sm C phase in higher homologues.
Carbazole-based π-conjugated polyazomethines: Effects of catenation and comonomer insertion on optoelectronic features
Garbay,Muccioli,Pavlopoulou,Hanifa,Hadziioannou,Brochon,Cloutet
, p. 274 - 284 (2017/05/31)
A series of carbazole-based polyazomethines have been synthesized under micro-wave irradiation and without transition-metal based catalyst. The impact of both the catenation brought by the carbazole subunits and the insertion of a co-monomer, i.e. 3,4 ethylene dioxythiophene (EDOT), on the optical and electrochemical properties have been studied. Among the different polyazomethines synthesized, the best in terms of optical and electrochemical properties has been found to be the one with the azomethine function linked in positions 2,7 of carbazole subunits. Upon the insertion of the EDOT comonomer, an increase of the molecular weight and a red-shift in the absorption spectra has been observed, corresponding to a diminution of the electronic gap.
Low Oxidation Potential Tetrathiafulvalene Analogues Based on 3,4-Dialkoxythiophene π-Conjugating Spacers
Akoudad, Said,Frere, Pierre,Mercier, Nicolas,Roncali, Jean
, p. 4267 - 4272 (2007/10/03)
Tetrathiafulvalene analogues involving dihexyloxythiophene (1), ethylenedioxythiophene (2), and bis(3,4-dihexyloxy-2-thienyl)ethylene (3) as conjugating spacer and diversely substituted at the 1,3-dithiole ring (R) have been synthesized. Electronic absorption spectra show the expected decrease of HOMO-LUMO gap when increasing the electron-releasing power of R or the length of the conjugating spacer. Cyclic voltammetry (CV) shows that whereas compounds 1 and 2 are reversibly oxidized into their cation radical and dication through two one-electron steps, for compounds 3 the dication is formed directly via a two-electron transfer. Comparison of the data for compounds 2 and 3 with those of their respective analogues based on thiophene and dithienylethylene shows that introduction of the electron-donating alkoxy groups at the 3 and 4 positions of the thiophene ring produces a 150-200 mV negative shift of the first redox potential (E°1). On the other hand, CV data for compounds 1 and 2 reveal several unusual features such as E°1 ≈ 0.10 V/SCE ranking among the lowest known to date and a Coulombic repulsion between positive charges in the dication larger than for the analogue π-donors based on unsubstituted thiophene. These results are interpreted by a major reorganization of the electronic distribution in the donor molecule due to alkoxy groups: the highest electron density moving from the 1,3-dithiole moiety toward the central thiophene ring.
Functionalizafion of 3,4-ethylenedioxythiophene
Mohanakrishnan,Hucke, Andre,Lyon, Michael A.,Lakshmikantham,Cava, Michael P.
, p. 11745 - 11754 (2007/10/03)
Syntheses of 3,4-ethylenedioxythiophene-based vinylenes and oligomers are reported.
New conjugated systems with multiple redox states
Raimundo,Akoudad,Brisset,Roncali
, p. 1234 - 1237 (2007/10/03)
New linear π-conjugated systems based on the association of thiophene- based donors and an acceptor group derived from indan-l,3-dione have been synthesized. Electrochemical and optical data are consistent with a small HOMO-LUMO gap and strong electron-acceptor properties.
