469912-82-1

Usage

Uses

Used in Organic Electronic Devices:
2,5-bis(triMethylstannyl)thieno[3,2-b]thiophene is used as a copolymer in the synthesis of thiophene-based materials for the fabrication of organic electronic devices such as organic field effect transistors (OFETs), organic thin film transistors (OTFTs), and organic photovoltaic cells (OPVs). Its application in these devices is due to its improved charge mobility and ability to form copolymers with enhanced properties.
Used in Conducting Polymers:
In the field of conducting polymers, 2,5-bis(triMethylstannyl)thieno[3,2-b]thiophene is used as a key component in the formation of hole transporting materials (HTM). Its application in this area is attributed to its ability to improve charge mobility, which is crucial for the performance of electronic devices.
Used in Polymerization:
2,5-bis(triMethylstannyl)thieno[3,2-b]thiophene is also used in the polymerization process to create new thieno(3,2-b)thiophene based polymers. These polymers have potential applications in various electronic devices due to their unique properties, such as improved charge mobility and enhanced performance.

Upstream product

• 1066-45-1 trimethyltin(IV)chloride 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 251-41-2 thieno[3,2-b]thiophene 
• 1723-27-9 thieno[3,2-b]thiophene-2-carboxylic acid 
• 201004-08-2 ethyl thieno[3,2,-b]thiophene-2-carboxylate 
• 25121-87-3 2,5-dibromothieno[3,2-b]thiophene 

Downstream Products

• 1372768-50-7 C₇₂H₉₂O₆S₄ 
• 1372768-51-8 C₇₂H₈₈O₄S₄ 
• 1008531-82-5 2,5-bis(3-hexylthiophen-2-yl)thieno[3,2-b]thiophene 
• 1369360-49-5 C₂₄H₂₀O₄S₂ 
• 1369360-51-9 C₇₆H₉₂O₄S₂ 
• 1369360-50-8 C₇₆H₉₆O₆S₂ 

Relevant academic research and scientific papers

Synthesis and redox property of the binuclear Pt(II) complexes bridged by thieno[3,2-b]thiophenes

The binuclear Pt(II) complexes bridged by thieno[3,2-b]thiophenes were prepared and their redox behavior was measured by cyclic voltammetry. The complexes showed two one-electron quasi-reversible waves and their first redox potentials are comparable with that of ferrocene. The oxidation potentials of the complexes and the related complexes are explained by the result of the MO calculation. The one-electron oxidation of some complexes gave stable oxidized complexes which showed no IT band in the near infrared region. The electronic and EPR spectra suggest that an unpaired electron is localized on the Pt atom.

Synthesis and characterization of thieno[3,2-b]thiophene-isoindigo-based copolymers as electron donor and hole transport materials for bulk-heterojunction polymer solar cells

A novel class of thieno[3,2-b]thiophene (TT) and isoindigo based copolymers were synthesized and evaluated as electron donor and hole transport materials in bulk-heterojunction polymer solar cells (BHJ PSCs). These π-conjugated donor-acceptor polymers were derived from fused TT and isoindigo structures bridged by thiophene units. The band-gaps and the highest occupied molecular orbital (HOMO) levels of the polymers were tuned using different conjugating lengths of thiophene units on the main chains, providing band-gaps from 1.55 to 1.91 eV and HOMO levels from -5.34 to -5.71 eV, respectively. The corresponding lowest unoccupied molecular orbital (LUMO) levels were appropriately adjusted with the isoindigo units. Conventional BHJ PSCs (ITO/PEDOT:PSS/active layer/interlayer/Al) with an active layer composed of the polymer and PC 71BM were fabricated for evaluation. Power conversion efficiency from a low of 1.25% to a high of 4.69% were achieved with the best performing device provided by the D-π-A polymer with a relatively board absorption spectrum, high absorption coefficient, and more uniform blend morphology. These results demonstrate the potential of this class of thieno[3,2-b]thiophene-isoindigo- based polymers as efficient electron donor and hole transport polymers for BHJ PSCs.

High-performance conjugated terpolymer-based organic bulk heterojunction solar cells

Recently, conjugated terpolymers comprising three components have attracted tremendous attention. However, quite a few examples of high-performance terpolymers have been reported. We present here two novel terpolymers named PtDDA and PtDAA, in which bithiophene (BT) and benzo[1,2-c:4,5-c′]dithiophene-4,8-dione (T1) were chosen as the donor and acceptor units, respectively. Thieno[3,2-b]thiophene (TT) and thiazolo[5,4-d]thiazole (TTz) were used as the third component. It is interesting to find that the PtDDA terpolymer shows a typical D1-D2-D1-A1 structure while PtDAA shows a D1-A1-D1-A2 structure. Without using additives or post-annealing processes, PtDAA-based solar cells show a high PCE of 8.1%, with an unprecedented fill factor (FF) of 0.74, which is much higher than those of PtDDA-based devices (PCE = 3.4%, FF = 0.55). The high efficiency of 8.1% is one of the highest values reported so far for organic solar cells based on conjugated terpolymers. The high performance is mainly ascribed to the efficient carrier transport in the PtDAA:PC71BM active layer, high crystallinity of PtDAA, and high domain purity. The results suggest that constructing conjugated terpolymers with one donor and two acceptor units is an effective strategy for designing high-performance solar cell materials.

Synthesis and characterization of S,N-heterotetracenes

The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and nitrogen heteroatoms were synthesized in multistep synthetic routes. A Buchwald-Hartwig amination of brominated precursors, thermolysis of azide precursors, and a Cadogan reaction of nitro-substituted precursors were successfully applied to eventually build-up pyrrole rings to stable and soluble fused systems. The various obtained heteroatom sequences 'SSNS' (SN4), 'SNNS' (SN4''), and 'NSSN' (SN4') allowed for evaluation of structure-property relationships relative to the sulfur analogue tetrathienoacene ('SSSS'). In line with the results for the whole series of S,N-heteroacenes, we find that replacement of sulfur by nitrogen atoms in the tetra- and hexacyclic systems leads to a red-shift in absorption, a decrease in oxidation potential and energy gap. On the other hand, the replacement of a thiophene ring by benzene leads to the opposite effects.

Conjugated polymer for organic thin-film transistor comprising of Quinoxaline and Thieno[3,2-b]thiophene

The present invention refers to [...] thieno [3, 2-b] thiophene using organic thin film transistor (organic thin-film transistor, OTFT) (conjugated polymer) relates to conjugated macromolecule type transition for electrolyte, more particularly 2, 3-bis (4- [...]) [...] -5, 8-(2, -5, 8-dibromoquinoxaline 3-Bis (4-hexylphenyl)) and 2, 5-bis (tri-n-methyl [...])-thieno [3, 2-b] thiophene (2, 5-Bis (Tri-n-methylstannyl)-thieno [3, 2-b] thiophene) Stille-coupling reactions of a produced through forging by use of conjugated macromolecule relates to (conjugated polymer). The present invention according to a heat conjugated macromolecule , each -3.3eV and -5.1eV HOMO and a LUMO value, the (band gap energy) 1.8eV band gap energy to useful as for anti-organic solar cells can be used. (by machine translation)

Effects of Chemical Composition, Film Thickness, and Morphology on the Electrochromic Properties of Donor-Acceptor Conjugated Copolymers Based on Diketopyrrolopyrrole

A series of diketopyrrolopyrrole (DPP) and propylenedioxythiophene (ProDOT)-containing random copolymers with different donor-to-acceptor ratios is synthesized through Stille coupling polymerizations. The low-bandgap polymers display dark tones with colors ranging from magenta to blue, and reveal reversible colored-to-transmissive electrochromism in absorption/transmission-type devices with high optical contrasts (up to 48 and 77 in the visible and near-infrared regions, respectively), modest switching speeds (a few to tens of seconds) and coloration efficiencies (267-5742C-1), as well as good long-term ambient redox stabilities. The structure-performance relationship of the polymers, in particular, the role of donor-to-acceptor ratio, is investigated, and it is shown that an increase in the amount of acceptor in the polymers leads to slower oxidative but faster reductive switching, accompanied with enhancement of the redox stability. In addition, further study on the influence of film thickness and film morphology reveals that devices with higher optical contrasts are attainable from thicker polymer films at the expense of switching speeds; films with high uniformity and connectedness together with open, loose structures at submicron to micron scale are favorable for achieving good electrochromic performance. On and off: A series of electrochromic diketopyrrolopyrrole-based conjugated polymers are synthesized and characterized. Reversible colored-to-transmissive optical changes with high contrasts and ambient redox stabilities are observed (see figure). The influences of donor-to-acceptor ratio and film morphology on the electrochromic performance are addressed.

HETEROACENE COMPOUNDS FOR ORGANIC ELECTRONICS

The present invention provides compounds of formula (1) wherein o is 1, 2 or 3, p is 0, 1 or 2, n is 0, 1 or 2, m is 0, 1 or 2, and A is a mono-or polycyclic ring system, which may contain at least one heteroatom, and an electronic device comprising the compounds as semiconducting material.

LEAVING SUBSTITUENT-CONTAINING COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, ORGANIC SEMICONDUCTOR FILM CONTAINING THE MATERIAL, ORGANIC ELECTRONIC DEVICE CONTAINING THE FILM, METHOD FOR PRODUCING FILM-LIKE PRODUCT, PI-ELECTRON CONJUGATED COMPOUND AND METHOD FOR PRODUCING THE PI-ELECTRON CONJUGATED COMPOUND

A leaving substituent-containing compound including a partial structure represented by the following General Formula (I): where a pair of X1 and X2 or a pair of Y1 and Y2 each represent a hydrogen atom; the other pair each represent a group selected from the group consisting of a halogen atom and a substituted or unsubstituted acyloxy group having one or more carbon atoms; a pair of the acyloxy groups represented by the pair of X1 and X2 or the pair of Y1 and Y2 may be identical or different, or may be bonded together to form a ring; R1 to R4 each represent a hydrogen atom or a substituent; and Q1 and Q2 each represent a hydrogen atom, a halogen atom or a monovalent organic group, and may be bonded together to form a ring.

LEAVING SUBSTITUENT-CONTAINING COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL FORMED THEREFROM, ORGANIC ELECTRONIC DEVICE, ORGANIC THIN-FILM TRANSISTOR AND DISPLAY DEVICE USING THE ORGANIC SEMICONDUCTOR MATERIAL, METHOD FOR PRODUCING FILM-LIKE PRODUCT, PI-ELECTRON CONJUGATED COMPOUND AND METHOD FOR PRODUCING THE PI-ELECTRON CONJUGATED COMPOUND

A leaving substituent-containing compound represented by General Formula (I), wherein the leaving substituent-containing compound can be converted to a compound represented by General Formula (Ia) and a compound represented by General Formula (II), by applying energy to the leaving substituent-containing compound, in General Formulas (I), (Ia) and (II), X and Y each represent a hydrogen atom or a leaving substituent, where one of X and Y is the leaving substituent and the other is the hydrogen atom; Q2 to Q5 each represent a hydrogen atom, a halogen atom or a monovalent organic group; Q1 and Q6 each represent a hydrogen atom or a monovalent organic group other than the leaving substituent; and among the monovalent organic groups represented by Q1 to Q6, adjacent monovalent organic groups may be linked together to form a ring.

ORGANIC ELECTRONIC DEVICES AND POLYMERS, INCLUDING PHOTOVOLTAIC CELLS AND DIKETONE-BASED POLYMERS

Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising formula (I); Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.