37882-75-0

Basic information

• Product Name: Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde
• Synonyms: Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde;Thieno[3,2-b]thiophene-2,5-dicarbaldehyde;Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde
• CAS NO: 37882-75-0
• Molecular Formula: C₈H₄O₂S₂
• Molecular Weight: 196.24616
• Mol File: 37882-75-0.mol

Chemical Properties

• Melting Point: 274°C(dec.)(lit.)
• Boiling Point: 388.1°C at 760 mmHg
• Flash Point: 188.5°C
• Appearance: /
• Density: 1.559g/cm³
• Vapor Pressure: 3.14E-06mmHg at 25°C
• Refractive Index: 1.811
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde(37882-75-0)
• EPA Substance Registry System: Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde(37882-75-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 37882-75-0(Hazardous Substances Data)

Usage

Uses

Used in Dye-Sensitized Solar Cells (DSSC) Industry:
Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde is used as a key component in the synthesis of novel metal-free organic dyes for DSSC. The application reason is that these dyes have demonstrated the ability to achieve high conversion efficiencies, with a notable example reaching up to 6.23%. This makes the molecule a promising candidate for improving the performance and efficiency of DSSCs, which are an important area of research and development in the field of renewable energy and sustainable technology.

InChI:InChI=1/C8H4O2S2/c9-3-5-1-7-8(11-5)2-6(4-10)12-7/h1-4H

Upstream product

• 251-41-2 thieno[3,2-b]thiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 82014-59-3 2,3-dihydro-3-oxothieno<3,2-b>thiophen 
• 6267-14-7 3-(carboxymethylsulfanyl)thiophene 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 603-35-0 triphenylphosphine 
• 84466-16-0 2,5-distyrylthieno[3,2-b]thiophene 
• 1361012-89-6 2,5-bis[p-(butylphenyl)vinyl]-thieno[3,2-b]thiophene 
• 1361012-90-9 2,5-bis[p-(hexylphenyl)vinyl]-thieno[3,2-b]thiophene 
• 1361012-91-0 2,5-bis[p-(hexylphenyl)vinyl]-thieno[3,2-b]thiophene 
• 1431984-44-9 2,5-bis{(E)-2-[4-(tert-butylsulfanyl)phenyl]ethenyl}thieno[3,2-b]thiophene 
• 1429623-05-1 5-(2,6-diphenyl-4H-pyran-4-ylidenemethyl)thieno[3,2-b]thiophen-2-carbaldehyde 
• 1429623-07-3 (E)-3-(5-(2,6-diphenyl-4H-pyran-4-ylidenemethyl)thieno[3,2-b]thiophen-2-yl)acrylaldehyde 
• 1429622-94-5 5-[5-(2,6-diphenyl-4H-pyran-4-ylidenemethyl)thieno[3,2-b]thiophen-2-ylmethylen]-1,3-diethyl-2-thioxodihydropyrimidin-4,6-dione 
• 1429622-96-7 (E)-5-[3-(5-(2,6-diphenyl-4H-pyran-4-ylidenemethyl)thieno[3,2-b]thiophen-2-yl)alylidene]-1,3-diethyl-2-thioxodihydropyrimidin-4,6-dione 
• 1429622-97-8 (E)-2-(3-cyano-4-(2-(5-(2,6-diphenyl-4H-pyran-4-ylidenemethyl)thieno[3,2-b]thiophen-2-yl)vinyl)-5,5-dimethylfuran-2(5H)-ylidene)malononitrile 
• 1429622-99-0 2-(3-cyano-4-((1E,3E)-4-(5-((2,6-diphenyl-4H-pyran-4-ylidene)methyl)thieno[3,2-b]thiophen-2-yl)buta-1,3-dienyl)-5,5-dimethylfuran-2(5H)-ylidene)malononitrile 

Relevant articles and documents

A highly emissive distyrylthieno[3,2-b]thiophene based red luminescent organic single crystal: Aggregation induced emission, optical waveguide edge emission, and balanced ambipolar carrier transport

A highly emissive red luminescent single crystal which shows aggregation induced emission (AIE) property and optical waveguide edge emission based on small organic functional molecule, cyano-substituted 2,5-di((E)-styryl)thieno[3,2-b]thiophene (CNP2V2TT) has been prepared by the physical vapor transport (PVT) method. The fluorescence quantum efficiency of crystal is up to 37% and an emission peak maximum (λmax) locates at 645 nm. Cystallographic data indicate that uniaxially oriented molecular packing with slipped face-to-face π-π stacking forms by the hydrogen bonding network among CNP2V2TT molecules. The single crystal FET devices were fabricated using Au and Ca as hole and electron injection electrodes, respectively. The molecular design, introducing cyano groups into molecular skeleton, effectively lower the LUMO level and achieve well-balanced ambipolar electron (0.13 cm2 V-1 s-1) and hole (0.085 cm2 V-1 s-1) mobilities.

Highly Efficient and Stable Dion?Jacobson Perovskite Solar Cells Enabled by Extended π-Conjugation of Organic Spacer

2D Dion–Jacobson (DJ) perovskites have become an emerging photovoltaic material with excellent structure and environmental stability due to their lacking van der Waals gaps relative to 2D Ruddlesden–Popper perovskites. Here, a fused-thiophene-based spacer, namely TTDMAI, is successfully developed for 2D DJ perovskite solar cells. It is found that the DJ perovskite using TTDMA spacer with extended π-conjugation length exhibits high film quality, large crystal size and preferred crystal vertical orientation induced by the large crystal nuclei in precursor solution, resulting in lower trap density, reduced exciton binding energy and oriented charge transport. As a result, the optimized 2D DJ perovskite device based on TTDMA (nominal n?= 4) delivers a champion PCE up to 18.82%. Importantly, the unencapsulated device based on TTDMA can sustain average 99% of their original efficiency after being stored in N2 for 4400 h (over 6 months). Moreover, light, thermal, environmental and operational stabilities are also significantly improved in comparison with their 3D counterparts.

ORGANIC COMPOUND, ORGANIC THIN FILM, AND ELECTRONIC DEVICE

Disclosed are an organic compound selected from a compound represented by Chemical Formula 1A, a compound represented by Chemical Formula 1B, and a combination thereof, an organic thin film including the organic compound, an organic thin film transistor, and an electronic device. The organic compound has liquid crystal properties and exhibits an ordered liquid crystal phase when being heated in a liquid crystal period due to asymmetric substituents and thereby charge mobility may be further improved.

Synthesis and properties of thieno[3,2-b]thiophene derivatives for application of OFET active layer

A series of thieno[3,2-b]thiophene derivatives having styryl groups were synthesized via short steps and characterized by UV-vis absorption spectra and cyclic voltammetry. Based on these results, we found that the introduction of long chain alkyl groups to the terminal styryl groups leads to narrower HOMO-LUMO gaps and higher HOMO energy levels than the unalkylated styryl substituted molecules. Organic field-effect transistor (OFET) devices using these derivatives as the active layer were fabricated by a vacuum deposition process. It was demonstrated that these devices showed a relatively high hole mobility up to 3.5 × 10-2 cm2/Vs. These devices also showed a good stability, namely their mobilities did not decrease over 100 days in air. Therefore, these facts suggested that the introduction of long-chain alkylated styryl groups is an effective way to improve the hole mobilities in OFETs.

The synthesis of π-electron molecular rods with a thiophene or thieno[3,2-b]thiophene core unit and sulfur alligator clips

A series of short oligo(p-phenylene-ethynylene)- and oligo(p- phenylenevinylene)-type molecular rods with an electronically rich thiophene or thieno[3,2-b]thiophene core unit and sulfur anchoring groups (AcS-, t-BuS-) at the termini have been synthesised

Heteroacene compound, organic thin film comprising the compound, and electronic device comprising the thin film

A heteroacene compound includes a di-thieno-benzo-thieno-thiophene derivative, in which all six rings may be fused together, an organic thin film including the same, and an electronic device that includes the thin film as a carrier transport layer. The compound of example embodiments may have a compact planar structure to thus realize improved solvent solubility and processability. When the compound is applied to electronic devices, a deposition process or a room-temperature solution process may be applied, and as well, intermolecular packing and stacking may be efficiently realized, resulting in improved electrical properties, including increased charge mobility.

Heteroacene compound, organic thin film comprising the compound, and electronic device comprising the thin film

A heteroacene compound includes a di-thieno-benzo-thieno-thiophene derivative, in which all six rings are fused together, an organic thin film including the same, and an electronic device that includes the thin film as a carrier transport layer. The compound of example embodiments may have a compact planar structure to thus realize improved solvent solubility and processability. When the compound is applied to electronic devices, a deposition process or a room-temperature solution process may be applied, and as well, intermolecular packing and stacking may be efficiently realized, resulting in improved electrical properties, including increased charge mobility.

Linearly extended tetrathiafulvalene analogues with fused thiophene units as π-conjugated spacers

A new series of linearly extended tetrathiafulvalene analogues with thienothiophene and dithienothiophene π-conjugating spacers has been synthesized. Electronic absorption spectra present a vibronic fine structure typical for rigid conjugated systems. Investigation of the electrochemical behaviour of the new donors by cyclic voltammetry reveals the successive generation of stable radical cation and dication species. The crystallographic structure of a single crystal of a dication salt of TT-TTF(ClO4)2 has been analysed by X-ray diffraction. The dication presents a syn conformation stabilised by S...S intramolecular interactions. The quinoid structure expected for the spacer for the +2 oxidation state is clearly revealed by the bond lengths.

Liquid Crystalline Compounds in the Thiophene Series 2. Liquid Crystalline Azomethines, Azines and Vinylenes

Azomethines, azines, vinylenes and hexatrienes containing thiophene and thieno-thiophene systems have been synthesized and characterisized by their IR and 1H NMR spectra.The liquid crystalline properties of these compounds have been studied thermically and optically by their textures and are compared with the analogous compounds having benzene rings. - Key words: Liquid Crystalline Thiophene Derivatives, Thiophene Derivatives with Liquid Crystalline Phases, Azomethines with Liquid Crystalline Phases, Azines with Liquid Crystalline Phases, Vinylenes with Liquid Crystalline Phases