3779-27-9

Usage

Uses

Used in Optoelectronic Applications:
2,2'-Bithiophene-5-carboxaldehyde is used as a synthetic intermediate for the development of optoelectronic materials, such as:
1. BODIPY (boron dipyrromethene) derivatives, which are known for their strong fluorescence and potential use in bioimaging and sensing applications.
2. Oligothiophenes, which are conductive polymers with potential applications in organic solar cells, field-effect transistors, and light-emitting diodes.
3. Bithiophene fulleropyrrolidine, which can be used in the development of novel materials for photovoltaic and energy storage devices.
4. Azomethine phthalic diimides, which are of interest in the field of nonlinear optics and as potential candidates for organic light-emitting diodes (OLEDs).
Used in Pharmaceutical Applications:
2,2'-Bithiophene-5-carboxaldehyde is used as a synthetic intermediate for the development of pharmaceutical compounds, such as:
1. (2,2'-bithiophene-5-carbaldehyde)-4-nitrophenylhydrazone (BT-NPH), which can be synthesized through a reaction with 4-nitrophenylhydrazine and may have potential applications in the development of new drugs.

Upstream product

• 5370-19-4 5-iodothiophene-2-carbaldehyde 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 37496-13-2 2-(trimethylstannyl)thiophene 
• 123-91-1 1,4-dioxane 
• 6165-68-0 thiophene boronic acid 
• 4565-31-5 5-formyl-2-thiophencarboxylic acid 
• 3375-31-3 palladium diacetate 
• 497-19-8 sodium carbonate 
• 3515-30-8 5-hydroxymethyl-2,2'-bithiophene 
• 492-97-7 2,2'-Bithiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 188290-36-0 thiophene 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 

Downstream Products

• 336607-97-7 5-[(E)-(4-N,N-dimethylaminobenzylidene)methyl]-2,2'-bithiophene 
• 35946-14-6 4-[2,2']bithiophenyl-5-ylmethyleneamino-phenol 
• 35943-31-8 [2,2']bithiophenyl-5-ylmethylene-4-methyl-aniline 
• 1134-61-8 5-but-3-en-1-ynyl-[2,2']bithiophenyl 
• 162691-96-5 5-(3-p-hydroxyphenyl-3-oxo-1-propenyl)-2,2'-bithiophene 
• 1057657-12-1 2-[2,2'-bithiophen]-5-yl-(4,5-diphenyl)-1H-imidazole 
• 1147869-76-8 4,4'-bis(2-(2.2'-bithien-5-yl)vinyl)biphenyl 
• 1402154-81-7 C₄₈H₄₅NS₂ 
• 1385839-06-4 C₂₆H₁₈S₂ 
• 1417521-52-8 1,5-dimethyl-2-phenyl-4-(2-(5-(2-thienyl)thienyl)methylidene)amino-1H-pyrazo-3(2H)-one 
• 13130-50-2 2,5-bis(5-formylthiophen-2-yl)thiophene 
• 1442442-45-6 C₂₂H₂₀N₂O₄S₂ 
• 1448509-02-1 TPA-BT₃ 

Relevant academic research and scientific papers

Synthesis of Thiophene-Based Optical Ligands That Selectively Detect Tau Pathology in Alzheimer's Disease

The accumulation of protein aggregates is associated with many devastating neurodegenerative diseases and the development of molecular ligands able to detect these pathological hallmarks is essential. Here, the synthesis of thiophene based optical ligands

Rapid and sensitive detection of hypochlorite in ~100% aqueous solution using a bithiophene-based fluorescent sensor: Application to water analysis and live-cell imaging

A new bithiophene-based biocompatible fluorescent and colorimetric sensor 2TD capable of detecting hypochlorite (ClO?) in enviro/biosystem was successfully synthesized. This sensor 2TD underwent a highly specific and sensitive oxidation reaction with ClO? and produced a bithiophene aldehyde (2T-CHO) emitting strong blue fluorescence, which was strongly confirmed by 1H NMR, HRMS, FTIR and DFT calculation. The 2TD for detecting ClO? displays an ultra-fast response (25 s), great water-solubility (~100% aqueous solution), wide pH working range (7–11), excellent anti-interference capability, and ultra-sensitivity with low detection limit of 8.3 nM. Colorimetric test strips demonstrate that 2TD can be utilized as a cost-effective and efficient solid-state sensor for rapidly and conveniently sensing ClO? with great sensitivity in practical applications. With the robust applicability, the 2TD was successfully utilized to determine/image ClO? in environmental water and live-cells. More interestingly, this developed sensor 2TD could be used as an efficient test tool for ClO? sensing.

Novel protein kinase C inhibitors: Synthesis and PKC inhibition of β- substituted polythiophene derivatives

A series of β-substituted polythiophene derivatives was synthesized through palladium-catalyzed coupling reaction. Their structure-protein kinase C (PKC) inhibitory activity relationship was studied. The carboxaldehyde and hydroxymethyl derivatives of α-terthiophene were potent PKC inhibitors (IC50 = 10-7 M).

A novel dual-function bithiophene-Meldrum's acid based chemosensor for highly sensitive, colorimetric and fluorimetric detection of cyanide and hypochlorite and its applications

A dual-function bithiophene-Meldrum's acid based chemosensor 2TM was developed, which displayed ultrafast, colorimetric and fluorescence turn-on responses for CN? and ClO? with specific selectivity and high sensitivity. The sensor 2TM for CN? detection in DMSO/H2O (1/3, V/V) solution was based on the nucleophilic addition of CN? to sensor, which resulted in remarkable spectral and discernible color changes. Meanwhile, 2TM showed specific selectivity for ClO? in 100percent aqueous solution based on the sensing mechanism of oxidative cleavage of C[dbnd]C bond. The detection limits were obtained to be 0.96 μM for CN? and 48 nM for ClO?. The sensing mechanism of 2TM toward CN? and ClO? was investigated by job'plot, FTIR, 1H NMR, HRMS and optical spectra. The sensor 2TM loaded colorimetric test strips/supported silica measurements demonstrated to be a portable, eco-friendly and ultrafast device for real-time and on-site visual detection of CN? and ClO? in water by the naked eye. More importantly, sensor 2TM with excellent photophysical properties and low biotoxicity was successfully applied to detect CN? and ClO? in live cells and environmental water samples, as well as capable of monitoring CN? in the natural food samples, illustrating its practical utility in biological and environmental systems.

Photophysical, crystallographic, and electrochemical characterization of symmetric and unsymmetric self-assembled conjugated thiopheno azomethines

Novel conjugated azomethines consisting uniquely of thiophene units are presented. The highly conjugated compounds were synthesized by simple condensation of a stable diamino thiophene (2) with its complementary thiophene aldehydes. These interesting nitrogen-containing thiophene units exhibit variable reactivity leading to controlled aldehyde addition. Because of the different amino reactivity, a one-pot synthesis of unsymmetric and symmetric conjugated azomethines with varying number of thiophene units was possible by judicious choice of solvent and careful control of reagent stoichiometry. The resulting covalent conjugated connections are both reductively and hydrolytically resistant. The thermodynamically E isomer is formed uniquely for all of the azomethines synthesized, which is confirmed by crystallographic studies. These also demonstrated that the azomethine bonds and the thiophene units are highly planar and linear. The fluorescence and phosphorescence of the thiopheno azomethines measured are similar to those of thiophene analogues currently used in functional devices, but with the advantage of low triplet formation and band-gaps as low as 1.9 eV. The time-resolved and steady-state temperature-dependent photophysics revealed the thiopheno azomethines do not populate extensively their triplet manifold by intersystem crossing. Rather, their excited-state energy is dissipated predominantly by nonradiative means of internal conversion. Quasi-reversible electrochemical radical cation formation of the thiophene units was found. These compounds further undergo electrochemically induced oxidative cross-coupling, resulting in conjugated products that also exhibit reversible radical cation formation.

Bithiophene-based fluorescent sensor for highly sensitive and ultrarapid detection of Hg2+ in water, seafood, urine and live cells

Using Hg2+-promoted deprotection reaction, we have developed a new fluorescent turn-on sensor 2TS based on bithiophene fluorophore for Hg2+ detection. The sensing mechanism of 2TS towards Hg2+ was strongly proved by 1H NMR, FTIR, HRMS, UV–vis and fluorescence spectra. Remarkly, 2TS towards Hg2+ in 100% aqueous solution shows high sensitivity with a low detection limit of 19 nM, superior selectivity and ultra-rapid response of 20 s during a wide sensing pH range from 4 to 10. Taking advantage of the excellent properties, the low-cost sensor 2TS-based filter paper/TLC test strips were fabricated for visual, immediate and quantitative detection of Hg2+ in water, proving its applicability towards sensitive in-situ and on-site detection. Meanwhile, 2TS showed high analytical performance for Hg2+ detection in water, seafood as well as human urine samples. Moreover, thanks to the good water solubility, negligible cytotoxicity, good biocompatibility and cell-membrane permeability, 2TS was further applied to effectively image Hg2+ in live cells. Furthermore, the developed sensor 2TS acted as good fluorescent display material for Hg2+ with obvious color change.

Anthelmintic activity of a nanoformulation based on thiophenes identified in Tagetes patula L. (Asteraceae) against the small ruminant nematode Haemonchus contortus

The synthesis of thiophenic compounds, previously identified in Tagetes patula, revealed that 4-(5′-(hydroxymethyl)-[2,2′-bithiophene]-5-yl)but-3-yn-1-ol), or simply Thio1, has a pronounced in vitro anthelmintic effect against Haemonchus contortus, showing 100% efficacy in the egg hatch and larval development tests presenting EC50 = 0.1731 mg.mL?1 and EC50 = 0.3243 mg.mL?1, respectively. So, this compound was selected to preparation of a nanostructured formulation to be orally administered to Santa Inês sheep. In general, from the fecal egg count reduction test (FECRT), it was observed that the product kept the parasitic load in the digestive tract of the hosts stable, with eggs per gram of faeces (EPG) counts having a mean value mean = 2167.1, efficacy = 36,45%), thus protecting the animals from health risks caused by a massive nematode infestation. To better understand the mode of action of this thiophene derivative, in silico molecular modeling studies were carried out with the glutamate-activated chloride channel (GluCl), a well-known molecular target of anthelmintic compounds. Based on the affinity score (GlideScore = -5.7 kcal.mol?1) and the proposed binding mode, Thio1 could be classified as a potential GluCl ligand, justifying the promising results observed in the anthelmintic assays.

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

Two novel triads based on a diketopyrrolopyrrole (DPP) central core and two 4,4-difluoro-4-bora-3a,4a-diaza- s - indacene (BODIPY) units attached by thiophene rings have been synthesised having high molar extinction coefficients. These triads were characterised and used as donor materials in small molecule, solution processable organic solar cells. Both triads were blended with PC 71 BM as an acceptor in different ratios by wt % and their photovoltaic properties were studied. For both the triads a modest photovoltaic performance was observed, having an efficiency of 0.65%. Moreover, in order to understand the ground and excited state properties and vertical absorption profile of DPP and BODIPY units within the triads, theoretical DFT and TDDFT calculations were performed.

Donor–acceptor (E)-2-[2-(2,2′-bithiophen-5-yl)vinyl]benzo[d]thiazole: synthesis, optical, electrochemical studies and charge transport characteristics

Condensation of 2-methylbenzothiazole with 2,2′-bithiophene-5-carbaldehyde affords the title compound, a new chromophore. This compound was used for the doping of poly[9,9-bis(6-diethoxylphosphorylhexyl)fluorene], and the obtained composites demonstrated high electron mobility (1.50 × 10?4 cm2 V?1 s?1) in contrast to dopant-free matrixes.

Anchoring stability and photovoltaic properties of new D(-π-A) 2 dyes for dye-sensitized solar cell applications

This study deals with the synthesis and characterization of two new di-anchoring dyes for applications in dye-sensitized solar cells. The materials were designed with a branched D(-π-A)2 structure containing (i) a rigid alkyl-functionalized carbazole core as the donor part, (ii) one (DYE1) or two (DYE2) thiophene units as the π-bridge and (iii) a cyano-acrylic moiety as acceptor and anchoring part. Electrochemical impedance spectroscopy indicated that the injected electron lifetime is higher in the case of DYE2, probably due to the length of the π-spacer that, in combination with the alkyl chain on the carbazole unit, hampers the charge recombination with the electrolyte. Stability tests on TiO2-sensitized films revealed that the di-anchoring remarkably slows down the desorption process, which conversely is evident for classic reference dyes. The highest power conversion efficiency reaches 5.01% in the case of DYE2 with a photovoltage of 0.70 V and a photocurrent of 10.52 mA cm-2, substantially deriving from a broader absorption with respect to DYE1, as also confirmed by IPCE measurements. These results support the efforts aimed at the structural engineering of D(-π-A)2 dyes to design new, more efficient and stable organic sensitizers.