3141-26-2Relevant articles and documents
New copolymers with thieno[3,2-b]thiophene or dithieno[3,2-b:2′,3′-d]thiophene units possessing electron-withdrawing 4-cyanophenyl groups: Synthesis and photophysical, electrochemical, and electroluminescent properties
Vyprachticky, Drahomír,Demirtas, Ilknur,Dzhabarov, Vagif,Pokorná, Veronika,Ertas, Erdal,Ozturk, Turan,Cimrová, Věra
, p. 2629 - 2638 (2017)
New monomers containing 4-cyanophenyl (–PhCN) groups attached to a thieno[3,2-b]thiophene (TT) or dithieno[3,2-b:2′,3′-d]thiophene (DTT) structure were synthesized and characterized as 4-(2,5-dibromothieno[3,2-b]thiophen-3-yl)benzonitrile (Br–TT–PhCN) or 4,4′-(2,6-dibromodithieno[3,2-b:2′,3′-d]thiophene-3,5-diyl)dibenzonitrile (Br–DTT–PhCN). The Suzuki coupling of 9,9-dioctylfluorene-2,7-diboronic acid bis(1,3-propanediol)ester and the Br–TT–PhCN or Br–DTT–PhCN monomer was utilized for the syntheses of novel copolymers poly{9,9-dioctylfluorene-2,7-diyl-alt-3-(4′-cyanophenyl)thieno[3,2-b]thiophene-2,5-diyl} (PFTT–PhCN) and poly{9,9-dioctylfluorene-2,7-diyl-alt-3,5-bis(4′-cyanophenyl)dithieno[3,2-b:2′,3′-d]thiophene-2,6-diyl} (PFDTT–PhCN), respectively. The photophysical, electrochemical, and electroluminescent (EL) properties of these novel copolymers were studied. Their photoluminescence (PL) exhibited the same emission maximum for both copolymers in solution. Red-shifted PL emissions were observed in the thin films. The PL emission maximum of PFTT–PhCN was more significantly redshifted than that of PFDTT–PhCN, indicating more pronounced excimer or aggregate formation in PFTT–PhCN. The ionization potential (HOMO level) and electron affinity (LUMO level) values were 5.54 and 2.81 eV, respectively, for PFTT–PhCN and were 5.57 and 2.92 eV, respectively, for PFDTT–PhCN. Polymer light-emitting diodes (LEDs) with copolymer active layers were fabricated and studied. Anomalous behavior and memory effects were observed from the current–voltage characteristics of the LEDs for both copolymers.
Synthesis, electropolymerization and characterization of a cross-linked PEDOT derivative
Arias-Pardilla, Joaquin,Gimenez-Gomez, Pablo A.,De La Pena, Alejandro,Segura, Jose L.,Otero, Toribio F.
, p. 4944 - 4952 (2012)
The synthesis of a novel electropolymerizable monomer, 2,2′,3, 3′-tetrahydro-2,2′-bithieno[3,4-b][1,4]dioxine (THBTD), based on two 3,4-ethylenedioxythiophene (EDOT) moieties connected through the ethylenedioxy bridge is reported. The new monomer paves the way for the development of cross-linked networks based on the EDOT moiety. Polymer films were electrogenerated from monomeric solutions by consecutive potential sweeps or by flow of constant anodic currents and the polymer structure was studied using FTIR. The relationship between the mass of the electrogenerated polymer (after reduction) and the polymerization charge gives the productivity of the consumed charge (mg C-1) while the charge stored and delivered by the films was determined by cyclic voltammetry getting the specific charge (C g -1). Simultaneously with the electroinitiated polymerization a chemical polymerization occurs around the electrode by monomer protonation giving protonated and no electroactive polymer chains. This chemical polymerization was followed in solution by UV-Vis spectroscopy using different conditions. Productivities and specific charges change with the conditions of synthesis in opposite directions. The voltammetric control presents a main redox couple (0.54/0.50 V) and a strong reduction process at -2.89 V that only can be reoxidized at more anodic potentials than 0.3 V as usual for charge trapping effects. EQCM studies indicate a remarkable difference between PEDOT and poly(THBTD). While poly(THBTD) shows a predominantly reversible anionic exchange during oxidation from the neutral state, the parent pristine PEDOT presents a mixed anionic and cationic exchange. Electrochromic color changes from an intense blue color of the oxidized film to a clear orange color in the reduced films as observed by in situ UV-Vis spectroscopy. Interestingly, the electrochromic changes in poly(THBTD) are opposed to those of PEDOT. Both thiophene derivative polymers present a similar thermal degradation at 305 and 314 °C, respectively.
Synthesis and characterization of monomeric and polymeric Cu(II) complexes of 3,4-ethylenedioxythiophene-functionalized with cyclam ligand
Velauthamurty, Kuhamoorthy,Higgins, Simon J.,Rajapakse, R.M. Gamini,Bandara,Shimomura, Masaru
, p. 326 - 332 (2010)
A functionalized EDOT derivative with 1,4,8,11-tetraazacyclotetradecane (cyclam) ligand pendant to the ethylene bridge (4) and its complexes [M(4)(BF4)2], where M(II) = Cu(II), was prepared and characterized. Their electrochemical copolymerization with EDOT was studied. The electro-co-polymerized films were characterized by electrochemical methods, X-ray photoelectron spectroscopy and by X-ray fluorescence spectroscopy. The co-polymerization method was found to afford a good control of the metal concentration in the polymer matrix and represents a good technique for preparing electronically conductive polymers containing redox-active metal complexes.
Selective Debromination of Thiophene Derivatives by Electrochemical Reduction
Dapperheld, S.,Feldhues, M.,Litterer, H.,Sistig, F.,Wegener, P.
, p. 403 - 405 (1990)
The debromination of polybrominated derivatives is achieved by electrochemical reduction with good yields and high selectivity.
Isomeric effect of fluorene-based fused-ring electron acceptors to achieve high-efficiency organic solar cells
Cao, Fong-Yi,Cheng, Yen-Ju,Huang, Po-Kai,Su, Yen-Chen,Xue, Yung-Jing
supporting information, p. 5315 - 5322 (2020/03/19)
Acceptor-donor-acceptor (A-D-A) non-fullerene electron acceptors (NFEAs) using ladder-type donor structures have become the dominant n-type materials for achieving high-efficiency OSCs. In this work, two isomeric fluorene-based ladder-type structures FCTT (TT-C-F-C-TT) and FTCT (T-C-TFT-C-T) have been designed and synthesized. These two isomeric donors with the different fused-ring arrangement, molecular geometry, and side-chain placement were end-capped with the FIC acceptors to form two NFEAs FCTT-FIC and FTCT-FIC isomeric materials. Compared to FTCT-FIC using the thiophene (T)-terminal donor, FCTT-FIC with the thienothiophene (TT)-terminal donor has more evenly distributed side chains on both sides of the backbone and less steric hindrance near the FIC acceptors, which enables stronger antiparallel π-π packing among the end-groups to create a channel for efficient electron transport, as evidenced by the thin-film GIWAXS measurements. FCTT-FIC displayed a larger optical bandgap and deeper-lying energy levels than its FTCT-FIC isomer. Compared to the PBDB-T:FTCT-FIC device, the PBDB-T:FCTT-FIC device showed a higher PCE of 10.32% with an enhanced Jsc of 19.63 mA cm-2 and an FF of 69.14%. A PM6:FCTT-FIC device using PM6 as a p-type polymer achieved the highest PCE of 12.23%. By introducing PC71BM as the second acceptor to enhance the absorption at shorter wavelengths, optimize the morphology and facilitate electron transport, the ternary-blend PM6:FCTT-FIC:PC71BM (1 : 1 : 0.5 in wt%) device yielded the highest PCE of 13.37% with a Voc of 0.92 V, a higher Jsc of 19.86 mA cm-2, and an FF of 73.2%. This result demonstrated that the TT-terminal ladder-type donor is generally a better molecular design than the corresponding T-terminal ladder-type isomer for the development of new A-D-A NFEAs.
BLUE ELECTROCHROMIC COMPOUND, PREPARATION METHOD AND SUBASSEMBLY THEREOF
-
Paragraph 0058; 0060, (2016/10/04)
One class of blue thiophene electrochromic compounds include 3,4-(2,2-bis(2-oxo-3-phenylpropyl))propylenedioxythiophene, 3,4-(2,2-bis(2-oxo-3-phenylbutyl))propylenedioxythiophene, and 3,4-(2,2-bis(2-oxo-3-phenylamyl))propylenedioxythiophene. The thiophene electrochromic compounds can change color between blue and transparency. The thiophene compounds can be electropolymerized on the surface of the ITO glass to form a film. The film has characteristics of low driving voltage (within ±1V), fast response time, and large transmittance difference between colored-state and bleached-state (up to 77.5%). The thiophene electrochromic compounds can be used in the electrochromic window, rearview mirror, electrochomeric display, and the like.
