3,4-Vinylenedioxythiophene (VDOT): a new building block for thiophene-based π-conjugated systems

Abstract

The synthesis of the title compound and its use as a building block in pi-conjugated systems are presented.

A Dual‐Polymer Electrochromic Device with High Coloration Efficiency and Fast Response Time: Poly(3,4‐(1,4‐butylene‐(2‐ene)dioxy)thiophene)–Polyaniline ECD

“…(see the Supporting Information, Figure S1, Figure S2, and Figure S3) As revealed by the voltammograms, all of the PBueDOT electrodes showed similar curve shapes to that of the PEDOT electrode, thus suggesting that as the potential of the electrode changed, the intrinsic redox reactions of PBueDOT were found to be similar to that of PEDOT. However, upon replacing the alkylene bridge of the EDOT backbone with a butylenes group, positive shifts of two consecutive oxidation (approximately −0.8 V and 0 V) and reduction (approximately −0.9 V and −0.3 V) peak potentials were induced, thereby indicating that PBueDOT has a higher ionization potential than PEDOT, owing to the higher resistance resulting from the large alkylene dioxy rings between the polymer backbones, and that the neutral state should therefore be more stable in air 9e. On the other hand, for all of the PBueDOT electrodes, the absorbance of ππ* transition was essentially similar to that of the PEDOT electrode, as the color changed from an almost transparent sky blue color in the oxidized state to opaque dark blue color in the neutral state 8–9.…”

“…In this regard, the electrochemical polymerization time for the PBueDOT electrode could be optimized as 20 s, with a film thickness of approximately 230 nm, which is in good accordance with the SEM results. Expansion of the alkylenedioxy ring within the EDOT backbone was made in an attempt to improve the optical properties of the conducting polymer ECD, no remarkable enhancement was observed in the CE value when compared to PEDOT or PEDOT‐derived ECDs reported previously 9e. 10a–b,e…”

Oxidative Bond Formation in Dithienyl Polyphenylenes: Optical and Electrochemical Consequences

“…[3,5,6] The propensity of thiophene systems toward the formation of insoluble products along with the difficulty of controlling the properties of the resulting polymers have led to the strategy of using monomers containing multiple thiophene units. [7,8] Substituted bisthienyl-, dithienylethene-, and thiophene-oligomer monomers have given better control over both the band gap and the conductivity of the polymers formed upon oxidation. In all of these systems, the focus has been on the effect of the structural changes to the monomer on the resulting polymer.…”

Helical Carbon and Graphite Films Prepared from Helical Poly(3,4‐ethylenedioxythiophene) Films Synthesized by Electrochemical Polymerization in Chiral Nematic Liquid Crystals

“…The use of bis‐EDOT with a rigid, rod‐like molecular shape and a lower oxidation potential causes a directional polymer growth and the production of polymers with a high conversion rate, resulting in a fibril structure. In fact, the oxidation potential ( E pa ) of the EDOT dimer (0.9 V) is much lower than that of the EDOT monomer (1.5 V) 10. It is considered that the high planarity of EDOT itself also facilitates positive effects for the formation of the PEDOT fibrils.…”