Electrochromic properties of a poly(dithienylfuran) derivative featuring a redox-active dithiin unit

Abstract

A teraryl monomer containing a 1,4-dithiin-furan central unit has been synthesised and characterised by single crystal X-ray crystallography. The di(thienyl)furan monomer 11 was successfully polymerised electrochemically and shown to possess a lower electrochemical band gap than its terthiophene analogue (1.97 eV cf. 2.11 eV). The electrochromic properties of this polymer proved to be superior to PEDOT, with fast switching and reversible colour transformation at high colour contrast (CE = 212 cm(2) C-1 cf. 183 cm(2) C-1 for PEDOT at 95% optical switch)

Poly([1,4]Dithiino[2,3‐c]Furan): The Synthesis, Electrochemistry, and Optoelectronic Properties of a Furan‐Containing Polymer

“…Herein, we report the chemical synthesis of a soluble, modified polyfuran, poly(2,3‐bis(hexylthio)‐[1,4]dithiino[2,3‐c]furan) (hereafter referred to as PBDF), where a dithiin ring has been incorporated onto the backbone of the polymer chain. PBDF differs from our previously reported furan‐dithiin‐containing copolymer, a dithienylfuran polymer, in that it is completely fabricated from an all‐furan backbone. One specific interest in this material is that it is essentially an inverse analog of PEDOT (albeit with a vinylene bridge instead of an ethylene unit), with an oxygen atom in the aromatic ring and sulfurs in the fused heterocycles (see Scheme ).…”

“…Chemical polymerization to afford PBDF was carried out by initial bromination of furan 1 , resulting in compound 2 in 87% yield ( Scheme ). Yamamoto polymerization with nickel(0) resulted in the successful formation of PBDF, which was isolated following Soxhlet extraction with dichloromethane to afford a dark shiny brown powder in moderate yield (43%).…”

Thienopentathiepine: a sulfur containing fused heterocycle for conjugated systems and their electrochemical polymerization

“…5 and S4 †) indicate the formation of singly charged species ( polaron), while the lower energy bands at 1180, 1480, and 1160 nm correspond to the formation of doubly charged species (bipolaron), respectively. 32,33 The deviation in spectroelectrochemical experiments precisely comes at 850 nm ( Fig. 5a and b) which is due to the lamp change (deuterium to tungsten lamp) during the NIR region to VIS region transformation.…”

Biomass-Based Discrete Furan Oligomers as Materials for Electrochromic Devices

“…These furan oligomers were found to be stable and were found to possess remarkable properties, such as higher rigidity, better solubility, tighter packing, and higher fluorescence, compared to their more prominent heterocyclic analogues. − Moreover, furan can be derived from biomass resources and is known to be biodegradable . For instance, our research group has developed a number of ways of deriving furan derivatives from raw biomass. − Regarding the electrochromic properties of furan, several studies have shown that integrating furan into polymeric materials enhances polymer performance. − However, studies involving the use of all-furan-based materials for electrochromic applications remain sparse. The majority of these studies employed the use of polyfurans that were either produced by electrochemical − or synthetic means .…”