Structure and semiconductor performances zongfan duan1. Solidstate synthesis of a conducting polythiophene via an. A series of carbazolethiophene dimers, p1p9, were synthesized using suzukimiyaura and ullmann coupling reactions. Pdf new thiophene derivatives as antimicrobial agents. As a primary step to develop novel sidechain liquid crystalline conductive polythiophenes, we have synthesized a series of monosubstituted thiophene derivatives with phenylalkyl, phenoxyalkyl, and phenoxycyclohexyl group as a substituent and then polymerized them through chemical polymerization procedure. Chemical communication 2004 19, 2222 2223 photochemical polymerization of thiophene derivatives in aqueous solution sergey a. Thiophene has been selected because of its stability and versatility in lending itself to synthetic modification and hence forms links in chain structures for rodlike. New thiophene derivatives 4ae incorporating an imine group have been successfully synthesized and characterized. Synthesis of benzothiophene and indole derivatives through. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Thiophene has been selected because of its stability and versatility in lending itself to synthetic modification. Otherwise, in those cases, where the thiophene soxide does not exhibit a ch 3 substituent on the ring system, furans are often the main products along with deoxygenated thiophenes scheme 39. Similarly, 5nitro thiophene 2aldehyde gives 5nitro2thenylidenepaminobenzoic acid and 5nitro2thenylidenebarbituric acid. The latter reacted with hydrazine hydrate to give the hydrazine derivative 5 which was used to form the hydrazone derivatives 7a, b and 9a, b via its reaction with some carbonyl compounds.
Clean and efficient iodination of thiophene derivatives submitted by frederic gohier on fri, 10162015 15. Thiophene belongs to a class of heterocyclic compounds containing a five membered ring made up of one sulphur as heteroatom with the formula c 4 h 4 s. The reactions with a wide variety of organic halides lead to a. Zhang a1, zhou g, rong sb, johnson km, zhang m, kozikowski ap. Articaine6 is the most commonly used dental anesthetic in europe, and patrin27 is an inhibitor of the dna. Solidstate synthesis of a conducting polythiophene via an unprecedented heterocyclic coupling reaction. Synthesis and investigation of novel thiophene derivatives containing heteroatom linkers for solid state polymerization. New approaches for the synthesis of thiophene derivatives with antitumor activities. Condensation of thiophene2aldehyde with nitroethane gives 12thienyl2nitroprop1ene. In a simple, regiocontrolled, and transitionmetal free approach to access exclusively 3borylated thiophene derivatives, commercially available bchlorocatecholborane acts as a carbophilic lewis acid to activate the alkyne in readily synthesized zorganylthioenyne substrates. A method is proposed for the synthesis of 5acylamino2,3dimethylthiophene4carbaldehydes and 5acylamino2,3tetramethylenethiophene4carbaldehydes by the formylation of the corresponding thiophenes using the vilsmeier reaction. Synthesis of thiophene2thiol derivatives springerlink. Synthesis and antibacterial activity of novel thiophene derivatives.
Molecular structure of thiophene 1,1dioxides, thiophene soxides, and their derivatives article in chemistry of heterocyclic compounds 386. In conclusion, a series of carbazolethiophene derivatives p4p9 were prepared by means of suzukimiyaura and ullmann coupling reactions as key steps. Moreover, it produced the pyrazole derivatives 11a, b through its. Synthesis and proton nmr spectra in the 2aminothiophene series, chemischer informationsdienst, 1981, 12, 51wiley online library. The diacetylenic diesters react readily with hydrogen sulfide or nahs in acetone at ph 910 to give 2,5disubstituted thiopheries see table 1. Synthesis and characterization of new thieno3,2bthiophene derivatives article pdf available in molecules 1710. The solvent is evaporated and the residue is washed with h 2 o 20 ml and diethyl ether 5 ml, yielding the corresponding thiophene and benzobthiophene hydrazide derivatives 5ag, 6ag.
Looking for online definition of thiophene in the medical dictionary. We have examined for the first time the reaction of diacetylenic diesters with hydrogen sulfide and with nahs. The desired product was obtained by filtration, washed with water, dried well and recrystallized. Condensation of thiophene 2aldehyde with paminobenzoic and barbituric acids gives 2thenylidene paminobenzoic acid and 2thenylidenebarbituric acid. Description since thiophene very often yields compounds that are analogous to benzene derivatives in general physiological properties, it was decided to attempt to prepare the nitro and amino derivatives of 1,1,1trichloro2,2bis2thienylethane v as well as the nitro and amino derivatives of 2,2,3. Spectrum chemical offers fine chemicals in lab and production sizes. Thiophene derivatives with multiple substitutions are prepared from vinylidene bromide, which is synthesized by the reaction of thiophene 2carboxaldehyde with carbon tetrabromide in the presence of pph 3, as a core molecule through several coupling reactions such as suzukimiyaura coupling and palladiumcatalyzed ch arylation. Fivemembered rings with one heteroatom together with their benzo and other carbocyclicfused derivatives.
The reaction of either cyclohexanone or cyclopentanone with cyanoacetylhydrazine and elemental sulfur gave the 2aminocycloalkenobthiophene derivatives 3a and 3b, respectively. Thus, in this paper, we would like to present an efficient metalfree synthesis of the. Four linear oligothiophenes containing 4, 5 and 7 thiophene rings substituted by a variable number of octyl chains attached at the betaposition of some of the thiophene rings and possessing a. Condensation of thiophene 2aldehyde with nitroethane gives 12thienyl2nitroprop1ene. Phenylenethiophene oligomer derivatives for thinfilm. Structureperformance relationship was studied with the aid of theoretical calculation. Synthesis of thiophenecontaining conjugated polymers from. Request pdf the synthesis of 3hnaphthol1,8 bcthiophene derivatives methods for the synthesis of keto derivatives of the little studied naphtho1,8bc thiophene system have been developed. Thiophene and its derivatives exist in petroleum or coal. Thiophene and pyrrole derivative polymers electrosynthesized on stainles steel. Phenylenethiophene oligomer derivatives for thinfilm transistors. Download limit exceeded you have exceeded your daily download allowance. Synthesis, reactions and biological activity of some new.
Molecular structure of thiophene 1,1dioxides, thiophene s. Synthesis of new thiophene derivatives and their use as. A thiophene derivative from 1,2,3,5tetraoacetyl4thiod. Scientific paper new approaches for the synthesis of thiophene derivatives with antitumor activities rafat m. The nitration of 2formylthiophene, 2acetothienone, and unsaturated ketones of the thiophene series with copper and aluminum nitrates in acetic anhydride at various temperatures was studied.
Synthesis of thiophene derivatives via palladiumcatalyzed. Ibrahim3 1 departrment of chemistry, faculty of science, cairo university, giza, a. New approaches for the synthesis of thiophene derivatives. Our objective is to arouse curiosity and interest in thiophene derivatives as organic materials and furnish some basic information and references useful to the reader as a trace to deepen the knowledge on the topics that heshe will consider most important. A new series of thiophene analogues was synthesized and checked for their in vitro antibacterial, antifungal, antioxidant, anticorrosion and anticancer activities. Carbohydrate research 7 note a thiophene derivative frorn 1,2,3,6tetra0acetyl 4thiodribofuranose r. Thiocyanation of 2acylaminothiophenes and synthesis of thieno2,3dthiazoles. Synthesis and cytotoxicity of fused thiophene and pyrazole. Synthesis and characterization of pushpull bithiophene. Received march 7th, 1969 during the course of synthesis of a nucleoside by condensation of 2,3,5tri0acetyl4thiodr. Recent advances in the synthesis of thiophene derivatives by. Hinsberg thiophene synthesis an overview sciencedirect. Complexes of thiophene derivatives as potential metallomesogens.
Synthesis of ringfluorinated thiophene derivatives based. Pdf synthesis and characterization of the novel thiophene. Jn are the arsenic derivatives of thiophene prepared by finzi12345 and steinkopf6 in these cases arsenic is substituted in one \ of the alpha positions whereas the other alpha position is 1 occupied by h, br, i, or ch3, all positive groups. Pdf the use of thiophene derivatives that have a stable structure in agriculture, food and pharmaceutical. Thiophene has been selected because of its stability and versatility in lending itself to synthetic modification and hence forms links in chain structures for rodlike metallomesogens.
Conclusions three new thiophene derivatives were synthesized. Chuong tusy, lili huang, jingpeng jin, jiangbin xia college of chemistry and molecular science, wuhan university, wuhan 430072, china. Synthesis of thiophenecontaining conjugated polymers from 2. In p1p9, carbazolethiophenes were linked at the n9 position for different core groups via biphenyl, dimethylbiphenyl, and phenyl. Clean and efficient iodination of thiophene derivatives. New method for the synthesis of 2thiophenecarboxylic. New method for the synthesis of 2thiophenecarboxylic acids. From the formyl derivatives obtained, previously unaccessible derivatives of thieno2,3bpyridine, thieno2,3dpyrimidine, and thieno3.
A thiophene derivative from 1,2,3,5tetraoacetyl4thio. A series of ethyl2substituted benzylideneamino4,5,6,7tetrahydrobenzob thiophene 3carboxylate derivatives were synthesized by using gewald synthesis and their structures were confirmed by ftir, ms and 1hnmr. Synthesis of thiophene derivatives by iodocyclization of scontaining. Therapeutic importance of synthetic thiophene springerlink. The reaction of 2amino3cyano4,5,6,7tetrahydrobenzob thiophene with chloroacetyl chloride gave the 2chloroacetamido derivative 3. The thiocyanation of 5acylaminothiophenes gives 4thiocyanato derivatives, the intramolecular cyclization of which gives 2acylaminothieno2,3d.
Thieno2,3b thiophene derivatives 1 was converted into the corresponding bromoketone2 85% using br 2 in refluxing acoh for 1 h. Solventfree and liquidphase iodination of thiophene derivatives. Synthesis and characterization of pushpull bithiophene and. Pdf synthesis and characterization of new thieno3,2b. Similarly, 5nitrothiophene2aldehyde gives 5nitro2thenylidenepaminobenzoic acid and 5nitro2thenylidenebarbituric acid. Thiophene and bioisostere derivatives as new mmp12 inhibitors. Pdf synthesis of new thiophene derivatives and their use as. Synthesis of thiophenecapped 2rotaxanes pdf free download.
Synthesis of new thiophene derivatives and their use as photostabilizers for rigid polyvinyl chloride january 2015 international journal of polymer science 20151. Syntheses of thiophene derivatives with liquid crystalline. Synthesis and investigation of novel thiophene derivatives. Thiophene definition of thiophene by medical dictionary. Halogenation of thiophene occurs very readily at room temperature and is rapid even at. Rapososynthesis and characterization of novel thieno3,2bthiophene based metal free organic dyes with different heteroaromatic donor moieties as sensitizers for dyesensitized solar cells. Condensation of thiophene2aldehyde with paminobenzoic and barbituric acids gives 2thenylidene paminobenzoic acid and 2thenylidenebarbituric acid. Synthesis and some properties of bisruthenocenylthiophene derivatives possible spincoupling in the twoelectron oxidized. New sulfides of the thiophene series were synthesized by reaction of thiophene 2thiol with compounds containing active halogen atoms and double bonds. Synthesis of thiophene derivatives containing a ferrocenyl radical. Synthesis of arylsubstituted thieno3,2bthiophene derivatives and their use for n,sheterotetracene construction. Synthesis of new thiophene derivatives and their use as photostabilizers for rigid polyvinyl chloride. This chapter covers aspects of the most recent developments in the synthesis and application of thiophene oligomers and polymers for use in a wide range of fields, from very efficient organic solar cells 2015nc10085 to fluorophores specifically binding amyloid fibrils formed inside neural cells in alzheimers and other neurodegenerative diseases.
Pdf synthesis of new thiophene derivatives and their use. Chapter three synthesis and applications of thiophene derivatives as organic materials. As a primary step to develop novel sidechain liquid crystalline conductive polythiophenes, we have synthesized a series of monosubstituted thiophene derivatives with phenylalkyl, phenoxyalkyl, and phenoxycyclohexyl group as a substituent and then polymerized them. Hoffman department of biochemistry, purdue university, lafayette, indiana 47907 u. Synthesis of some thiophene derivatives springerlink. This spectrum integrates for 10 protons, and is composed of three singlet signals. The rate of halogenation of thiophene at 25 c is about 10 8 times that of benzene.
This study involves the synthesis and structural characterization of new metal complexes of thiophene derivatives that have potential liquid crystalline properties. New sulfides of the thiophene series were synthesized by reaction of thiophene2thiol with compounds containing active halogen atoms and double bonds. Synthesis of new thiophene and benzobthiophene hydrazide. A formal thioboration and subsequent sulfur dealkylation provide 3. They occur in coal tar distillates the discovery of thiophene in coaltar benzene provides one of the classic anecdotes of organic chemistry. High molecular weight thiophenecontaining conjugated polymers were successfully synthesized by suzuki polycondensation of aryl dibromides and 2,5thiophenebisboronic acid derivatives by using a new thiophenecontaining bulky phosphorous compound as the ligand for a zerovalent palladium catalyst. Author links open overlay panel bunyarat rungtaweevoranit a akkarapol butsuri a krittaphat wongma a karoon sadorn a. Synthesis of novel derivatives of carbazolethiophene. Synthesis of thiophene derivatives and their antimicrobial. Synthesis of thiophene and no curcuminoids for antiinflammatory and anticancer activities.
Cyanoacetamide derivatives as synthons in heterocyclic synthesis. Synthesis of arylsubstituted thieno3,2bthiophene derivatives and. The reaction of either cyclohexanone or cyclopentanone with cyanoacetylhydrazine and elemental sulfur gave the 2aminocycloalkenob thiophene derivatives 3a and 3b, respectively. High molecular weight thiophene containing conjugated polymers were successfully synthesized by suzuki polycondensation of aryl dibromides and 2,5thiophenebisboronic acid derivatives by using a new thiophene containing bulky phosphorous compound as the ligand for a zerovalent palladium catalyst. Using thiophene as an example, it was demonstrated that the reaction is catalyzed not only by voacac2 but also by iron and molybdenum compounds. Electronic properties were evaluated by uvvis, cyclic voltammogram, and theoretical calculations. Photochemical polymerization of thiophene derivatives in. Pdf thiophene and bioisostere derivatives as new mmp12. A facile twostep synthesis of thiophene endcapped aromatic systems. Synthesis of ringfluorinated thiophene derivatives based on single cf bond activation of cf 3cyclopropanes. The synthesis of brdntt features chemoselective metalation and crosscoupling reactions that enable us to keep the 2bromo group intact from the starting material. Pdf thiophene and pyrrole derivative polymers electro. The synthesis of 3hnaphthol1,8bcthiophene derivatives.
Articaine6 is the most commonly used dental anesthetic in. Thiophene, when compared with 1,4disubstituted benzene units. Our objective is to arouse curiosity and interest in thiophene derivatives as organic materials and furnish some basic. The electronic structures were determined by uvvis, fluorescence spectral measurements, cv, and theoretical calculations. Synthesis and applications of thiophene derivatives as. The solventfree reaction of arylamines with ethyl cyanoacetate constitutes one of the most. The synthesis of thiopene derivatives from diacetylenic hydrocarbons has been described 1. Thiophene is taken from the word theion, the greek word for sulfur, and another greek word phaino which means shinning. At low temperatures 2acetothienone gives a mixture of 4 and 5nitro isomers, while 2formylthipphene gives only a 5nitrosubstituted compound in the diacetate form. The setback of drug resistance and generation of free radicals has promoted the researchers to study and explore for new compounds to combat. Thus the synthesis and characterization of novel thiophene moieties with wider therapeutic activity is a topic of interest for the medicinal chemist. Solventfree and liquid phase iodination of thiophene derivatives with potassium.
Metalfree synthesis of thiophenes 40 from 1,3diynes 39 and na2s 70. Convenient and improved methods of synthesis afforded dyes 5 and 7 in higher yields metal free ethynylbithiophene or ethynylthieno3,2bthiophene dyes for dssc. Synthesis of novel derivatives of carbazolethiophene, their. Of the iron and molybdenum compounds examined in the present study fecl3, febr2, feoac2, feacac 3, moo3, mocl5, moco6, feacac 3 and moco6 proved to be most efficient in this reaction. Introduction thiophene is a heterocyclic compound with formula c4h4s, it is colorless and has a mildly pleasant odor at room temperature. Nitration of thiophene analogs of ddt unt digital library.