3339-80-8

Upstream product

• 625-88-7 2,5-diiodothiophene 
• 492-97-7 2,2'-Bithiophene 

Downstream Products

• 83495-30-1 5,5′-diphenyl-2,2′-bithiophene 
• 115257-02-8 5,5'-bis(phenylethynyl)-2,2'-dithiophene 
• 1268160-21-9 S,S'',S'',S'''-{5,5'-[2,2'-bithiophene-5,5'-diylbis(ethyne-2,1-diyl)]-bis(benzene-5,3,1-triyl)}tetrakis(methylene)tetraethanethioate 
• 951791-16-5 1-[2-(2-butoxyethoxy)ethoxy]-4-[(5'-iodo-2,2'-bithien-5-yl)ethynyl]benzene 
• 175850-28-9 5,5'-di([1,1'-biphenyl]-4-yl)-2,2'-bithiophene 
• 88493-55-4 sexithiophene 

Relevant academic research and scientific papers

Synthesis of β-Methoxy, Methyl-Capped α-Oligothiophenes

The first syntheses of structurally defined methoxyoligothiophenes are described.Nine α-coupled oligothiophenes, dimers through hexamers, symmetrically substituted at the "inside" or "outside" β-positions with two or four methoxy groups, and with terminal methyl groups, were prepared.The electron-donor methoxy groups and terminal methyls have been shown to stabilize cationic species formed by oxidation or protonation of these oligomers.The oligomers were built up by the cross coupling of (mono- or oligo-) β-methoxy-α-iodothiophenes and (mono- or oligo-) α-stannylthiophenes catalyzed by Pd(0)/Pd(II) or by the redox homo-coupling of α-thienyllithium compounds with Fe(acac)3.Synthesis by the cross coupling of thienyl Grignard reagents and bromothiophenes with Ni(0) or Suzuki coupling using organoboranes was not successful.An X-ray crystal structure od a dimethoxy quaterthiophene is reported.

Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate

Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.

Conjugated Oligothiophene Derivatives Based on Bithiophene with Unsaturated Bonds as Building Blocks for Solution-Processed Bulk Heterojunction Organic Solar Cells

A new building block ATVTA that uses stiff carbon–carbon triple bonds (A) on 1,2-di(2-thienyl)-ethene (TVT) has been developed. Oligothiophene derivatives S-01 with a TVT unit, S-02 with a 5,5′-diethynyl-2,2′-dithienyl (AT2) unit and S-03 with ATVTA were synthesized to compare their effects in a systematic study. Due to the better π-conjugation extension of the TVT unit, S-01 exhibits the most red-shifted absorption profile among them, whereas S-02 possesses the deepest HOMO level. While the HOMO level of S-03 is down-shifted by 0.02 eV relative to that of S-01, the alkyne linkages can effectively down-shift the HOMO level. By replacing the terminal units of S-03 with stronger electron acceptors, S-04 and S-05 exhibited broader absorption profiles and lower HOMO levels than those of S-03. Organic solar cells based on these molecules were fabricated and an S-03:PC60BM (1:1, w/w) based device afforded the highest Voc value of 0.96 V and a power conversion efficiency (PCE) of 2.19 %.

Clean and Efficient Iodination of Thiophene Derivatives

Iodination of thiophene derivatives is realized using a simple, fast, and efficient methodology. Iodination of thiophene and 2- or 3-substituted or 3,4-disubstituted thiophenes with N-iodosuccinimide (NIS) activated with 4-toluenesulfonic acid in ethanol gives pure iodinated products that require no further purification.

One-pot, regioselective consecutive multihalogenation of 2,2′-bithiophene

The one-pot regioselective consecutive multihalogenation of 2,2′-bithiophene (1) was demonstrated. Compound 1 was consecutively halogenated with lithium halides such as lithium bromide, chloride, and/or iodide in the presence of lead tetraacetate in chloroform at room temperature or under reflux conditions to give 5-bromo(or chloro)-5′-iodo(or chloro)-, 3-bromo(or chloro)-5,5′-dibromo(or dichloro, diiodo)-, 3,3′-dibromo-(or dichloro)-5,5′-diiodo(or dibromo, dichloro)-, and 3,3′,5-tribromo(or trichloro)-5′-iodo(or bromo)-2,2′- bithiophenes. Notably, this process offers a regioselective method for consecutive multihalogenation in one pot, and the yields and selectivity are also higher than those obtained in the step-by-step and concurrent halogenation methods. Copyright

Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent

The green generation of X+ (X = Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quantitative for positions α to the sulfur; pyrroles also give quantitative reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as thiophenes with strongly electron-withdrawing groups showed little to no reactivity under the conditions investigated. The reaction shows remarkable functional group tolerance (to alcohol, nitro, alkyl, halo, and carbonyl groups), as shown through reaction with substituted phenols. In all bromination reactions, reaction yields and regiochemistry were very similar to reactions involving N-bromosuccinimide in tetrahydrofuran solvent.

Semiconducting polymer thin films by surface-confined stepwise click polymerization

Surface-confined stepwise click polymerization was used to prepare surface-attached thin films of semiconducting polymers. These highly uniform films showed extended UV/vis absorption characteristics and a remarkable degree of molecular organization with a unidirectional alignment of the polymer chains normal to the surface.

Generation of arylzinc reagents through an iodine-zinc exchange reaction promoted by a non-metallic organic superbase

Functionalized aryl and heteroaryl zinc reagents were prepared from aryl iodides and diethylzinc through t-Bu-P4 base-promoted iodine-zinc exchange reactions. The scope and limitations of this protocol, and several applications for the synthesis of oligoaryls and fused aromatics, are presented.

Molecular compound, luminous material using the same, and luminous element

Provided is a new molecular compound excellent in luminous property, which has a molecular structure wherein a thiophene ring and a benzene (or naphthalene) ring are directly bonded to each other, as a molecular compound making it possible to control its

Dramatically enhanced fluorescence of heteroaromatic chromophores upon insertion as spacers into oligo(triacetylene)s

In continuation of a previous study on the modulation of π-electron conjugation of oligo(triacetylene)s by insertion of central hetero-spacer fragments between two (E)-hex-3-ene-1,5-diyne ((E)-1,2-diethynylethene, DEE) moieties (Fig. 1), a new series of trimeric hybrid oligomers (14-18 and 22-24, Fig. 2) were prepared (Schemes 1-3). Spacers used were both electron-deficient (quinoxaline-based heterocycles, pyridazine) and electron-rich (2,2′-bithiophene, 9,9-dioctyl-9H-fluorene) chromophores. With 19-21 (Scheme 4), a series of transition metal complexes was synthesized as potential precursors for nanoscale scaffolding based on both covalent acetylenic coupling and supramolecular assembly. The UV/VIS spectra (Fig. 3) revealed that the majority of spacers provided heterotrimers featuring extended π-electron delocalization. The new hybrid chromophores show a dramatically enhanced fluorescence compared with the DEE dimer 13 and homo-trimer 12 (Fig. 5). This increase in emission intensity appears as a general feature of these systems: even if the spacer molecule is non-fluorescent, the corresponding hetero-trimer may show a strong emission (Table 2). The redox properties of the new hybrid chromophores were determined by cyclic voltammetry (CV) and rotating-disk voltammetry (RDV) (Table 3 and Fig. 5). In each case, the first one-electron reduction step in the hetero-trimers appeared anodically shifted compared with DEE dimer 13 and homo-trimer 12. With larger spacer chromophore extending into two dimensions (as in 14-18, Fig. 2), the anodic shift (by 240-490 mV, Table 3) seems to originate from inductive effects of the two strongly electron-accepting DEE substituents rather than from extended π-electron conjugation along the oligomeric backbone, as had previously been observed for DEE-substituted porphyrins.