Functional Thiophene Research Articles

LiBr-Promoted Reaction of β-Ketodithioesters and Thioamides with Sulfoxonium Ylides to Synthesize Functionalized Thiophenes.

An operationally simple and highly efficient synthesis of functionalized thiophenes has been developed by LiBr promoted heteroannulation of β-ketodithioesters and thioamides with bench-stable sulfoxonium ylides in open air for the first time. This one-pot strategy involves formal Csp3-H bond insertion/intramolecular cyclization cascade, featuring readily accessible starting materials, TM and additive-free condition, broad substrate scope, high functional group compatibility, and scalability. Moreover, the carbonyl, thiomethyl, and amino groups in the resulting thiophene provide a good handle on downstream transformations.

Investigation of Permeability Against Some Metals with a Functional Thiophene Based Polymeric Membrane Sensor

AbstractThere are many advantages of using membranes in the separation of wastewater, but their uses are limited because they are not reusable due to blockages in the membrane. In this study, alginate‐based poly(ethyl‐methacrylate) (PEMA) polymeric membranes containing previously synthesized IOS, which are known to be selective against Fe3+, were prepared and their permeability against heavy metals such as Cd2+, Co2+, Cu2+, Fe3+, Hg2+ and Pb2+ were investigated. The properties of membranes characterized by UV‐Vis and FT‐IR spectrophotometry, were investigated with analysis techniques such as SEM, contact angle measurements, TG‐DTG, DSC and AFM. As a result of the measurements taken from the UV spectrophotometer of the filtrates passed through various aqueous ion solutions of the membranes as mentioned above, it was concluded that the ion to which the membrane was most selective was the Fe3+ ion. Moreover, it could be said that thanks to the repeated filtration processes the membrane prepared retained some Fe3+ ion in each measurement and could be used many times in the filtration process. Resultantly, it is possible to say that the polymeric Fe3+ membrane sensor produced may be suitable for use when it is necessary to remove Fe3+ ion from a polluted aqueous environment.

Syntheses of Novel Tetrasubstituted Thiophenes from Benzene-1,2-Diamines, Ethyl Bromopyruvate, Malononitrile, and Aryl Isothiocyanates

Synthesis of highly functionalized tetrasubstituted thiophenes has been reported involving 3-(bromomethyl)quinoxalin-2(1H)-ones as activated halomethylene compounds precursors. Thus sequential base mediated condensation of readily available malononitrile with aryl isothiocyanates followed by S–alkylation of the resulting enethiolate salts with 3-(bromomethyl)quinoxalin-2(1H)-one compounds and concurrent intramolecular enamine type condensation of S–alkylated compounds affords substituted thiophenes in excellent yields.

Diversity-oriented approach to functional thiophene dyes by Suzuki coupling-lithiation one-pot sequences

Functional thiophenes, e.g. for organic metal-free dye sensitized solar cells (DSSC), are accessible efficiently via a divergent and diversity-oriented synthetic strategy.

Synthesis of Polysubstituted 3-Aminothiophenes from Thioamides and Allenes via Tandem Thio-Michael Addition/Oxidative Annulation and 1,2-Sulfur Migration.

A facile synthetic method for the construction of 3-aminothiophenes from readily available thioamides and alllenes in the presence of a TBAI/TBHP catalyst system was developed. This protocol represents an efficient and straightforward way to access highly functionalized thiophenes in moderate to excellent yields under mild conditions, via a tandem thio-Michael addition, oxidative annulation, and 1,2-sulfur migration pathway.

Fullerene Functionalized Thiophene Derivative as an Acceptor Material for Organic Photovoltaics

Research & Development in Material Science Fullerene Functionalized Thiophene Derivative as an Acceptor Material for Organic Photovoltaics Ranjith Kottokkaran*, Arun D Rao, Vinila NV and Praveen C Ramamurthy Department of Materials Engineering, Indian Institute of Science, India *Corresponding author: Ranjith Kottokkaran, Department of Materials Engineering, Indian Institute of Science, Bangalore, India Submission: August 17, 2017; Published: October 20, 2017 DOI: 10.31031/RDMS.2017.01.000520 ISSN : 2576-8840Volume1 Issue4

A convenient synthesis of new 5,11-dihydroindolo[3,2-b]carbazoles bearing thiophene, 2,2′-bithiophene or 2,2′:5′,2″-terthiophene units at C-2 and C-8 positions

A series of new 5,11-dihydroindolo[3,2-b]carbazole derivatives, containing functional thiophene, 2,2′-bithiophene or 2,2′:5′,2″-terthiophene moieties at both C-2 and C-8 positions of their fused scaffolds, have been obtained from 2,8-diacetyl-substituted 5,11-dihydroindolo[3,2-b]carbazole compounds through the effective strategy, which is based on the sequence of two reactions, namely the Vilsmeier–Haack formylation and the Fiesselmann thiophene synthesis. The starting acetyl substituted materials have been transformed into the corresponding 3-chlorocrylaldehyde-containing compounds by treatment with POCl3-DMF complex, followed by the reaction with alkyl thioglycolates or α-mercaptoacetone in the presence of triethylamine to afford 2-carboalkoxythiophene- or 2-acetylthiophene-linked derivatives. 2-Acetylthiophene derivatives have further been involved into the same sequence of reactions to obtain 2,2′-bithiophene-, and 2,2′:5′,2″-terthiophene-linked 5,11-dihydroindolo[3,2-b]carbazole compounds.

Water based surfactant-assisted synthesis of thienylpyridines and thienylbipyridine intermediates

The connection between heterocyclic systems by forming new CC bond is a relevant topic for the easy preparation of intermediates and functional dyes for technological applications. Several methods were developed in the last decades and the urge for sustainable synthetic chemical methods pushed us to prepare thienylpyridines and two thienylbipyridine ligands by the Suzuki reaction in aqueous CTAB micellar medium and in presence of a Pd catalyst. These intermediates can be found as component of dyes and functional thiophene monomers. Reaction conditions were optimized under both thermal and microwave (MW) activation obtaining good yields (70–93%) using Pd(PPh3)4 as catalyst. Two thienylbipyridine ligands were prepared and the transformation of one of them into a terthiophene-based bipyridine ligand was easily obtained by almost green methods and with very good yield. This clean and sustainable method can be proposed as a green step to obtain intermediates and final dyes for technological applications, such as CO2 reduction, in gram-multigram scale.

Construction of highly functionalized thiophene and benzo[b]thiophene derivatives via a sequence of propargyl–allenyl isomerization/cyclization/demethylation

An efficient one-pot protocol for the synthesis of functionalized thiophene and benzo[b]thiophene derivatives was developed via a sequence of propargyl–allenyl isomerization/cyclization/demethylation. As a result of the readily accessible starting materials, simple operation, and mild conditions, this reaction should have potential utility in organic synthesis.

ChemInform Abstract: Stereoselective Amine‐Thiourea‐Catalyzed Sulfa‐Michael/Nitroaldol Cascade Approach to 3,4,5‐Substituted Tetrahydrothiophenes Bearing a Quaternary Stereocenter.

AbstractAn organocatalytic reaction cascade towards highly functionalized thiophene derivatives is investigated.

Toward Network Electrochromic Film: Secondary Polymerization of Methacrylate Functionalized Thiophene

Toward Network Electrochromic Film: Secondary Polymerization of Methacrylate Functionalized Thiophene

ChemInform Abstract: Copper(I)‐Catalyzed Multicomponent Reaction Providing a New Access to Fully Substituted Thiophene Derivatives.

AbstractCondensation of α‐thiocyanate ketones with indole‐2,3‐diones gives aroylethanethiolates (IV), which readily undergo a Cu(I)‐catalyzed three‐component reaction with terminal alkynes and tosylazides to form highly functionalized thiophene derivatives through [3 + 2] cycloaddition of in situ generated azaheterocumulenes.

Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives.

Readily available triethylammonium 1-(2-oxoindolin-3-ylidene)-2-aroylethanethiolates are efficiently converted into a variety of fully substituted thiophene derivatives by copper(I)-catalyzed denitrogenative reactions with terminal alkynes and N-sulfonyl azides. This new reaction simultaneously installs C–N, C–S, and C–C bonds, allowing direct formation of highly functionalized thiophenes with a wide diversity in substituents in a one-pot manner. A plausible mechanism for the domino process is proposed.

ChemInform Abstract: Influence of Solvent and Substituents on the Reaction of N‐Alkylthioacetamides with Dimethyl Acetylenedicarboxylate: Synthesis of Functionalized Thiophenes Containing an Exocyclic Double Bond.

AbstractThe outcome of the reaction of thioacetamides with dimethyl acetylenedicarboxylate depends on the structure of thioacetamide substrates.

Continuous Flow Synthesis of Organic Electronic Materials – Case Studies in Methodology Translation and Scale-up

The continuous flow synthesis of functional thiophene derivatives was examined. Methodology for the lithiation of thiophene building blocks was developed using a commercial bench-top flow reactor. In addition, the advantages of flow processing were demonstrated in the synthesis of a high performance organic dye in gram scale.

Synthesis of highly functionalized thiophenes by three-component and one-pot reaction

Reaction between ethyl 2-cyano-3-arylacrylate and dialkyl acetylenedicarboxylates in the presence of KSCN at room temperature provided a simple and efficient one-pot route for the synthesis of highly functionalized thiophenes. The reaction is characterized by mild conditions, short reaction time and tolerance to various functional groups.

Synthesis of thiophenes and pyranone fused thiophenes by base induced inter and intramolecular C–S and C–C bond formation: a non-catalytic approach

An efficient and concise one pot synthesis of highly functionalized thiophenes and pyranone fused thiophenes has been delineated through base induced ring transformation of suitably functionalized 2H-pyran-2-ones by ethyl thioglycolate by inter and intramolecular C–S and C–C bond formation.

Efficient synthesis of highly substituted thiophenes from acetylenic esters, ethyl bromopyruvate, and tetramethylthiourea

The reaction of acetylenic esters with ethyl bromopyruvate in the presence of tetramethylthiourea led to highly functionalized thiophenes in excellent yields.

Quasi-Controlled Polymerization through a Nickel Catalyst Process of a Functionalized Thiophene Monomer: Kinetic Studies and Application to the Synthesis of Regioregular Poly(thiophene-3-acetic acid)

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTQuasi-Controlled Polymerization through a Nickel Catalyst Process of a Functionalized Thiophene Monomer: Kinetic Studies and Application to the Synthesis of Regioregular Poly(thiophene-3-acetic acid)P. Vallat, J.-P. Lamps, F. Schosseler, M. Rawiso, and J.-M. CatalaView Author Information Institut Charles Sadron (CNRS-ULP), 6 rue Boussingault, 67083 Strasbourg, France Cite this: Macromolecules 2007, 40, 7, 2600–2602Publication Date (Web):March 8, 2007Publication History Received11 July 2006Revised8 February 2007Published online8 March 2007Published inissue 1 April 2007https://doi.org/10.1021/ma0615506Copyright © 2007 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views759Altmetric-Citations38LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (54 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Catalysts,Monomers,Organic compounds,Polymerization,Reaction mechanisms Get e-Alerts

Synthesis of thiophenes and thieno[3,2-c]pyran-4-ones as antileishmanial and antifungal agents

Abstract A series of highly functionalized thiophene ( 2 ) and thieno[3,2-c]pyran-4-one( 4 ) derivatives have been synthesized and evaluated for their antileishmanial and antifungal activities.