4282-29-5Relevant academic research and scientific papers
Low-cost synthesis and physical characterization of thieno[3,4-c]pyrrole-4, 6-dione-based polymers
Berrouard, Philippe,Dufresne, Stephane,Pron, Agnieszka,Veilleux, Justine,Leclerc, Mario
, p. 8167 - 8173,7 (2012)
The improved synthesis of thieno[3,4-c]pyrrole-4,6-dione (TPD) monomers, including Gewald thiophene ring formation, a Sandmeyer-type reaction, and neat condensation with an amine, is presented. This protocol enables faster, cheaper, and more efficient preparation of TPD units in comparison to traditional methods. Furthermore, a series of TPD homo- and pseudohomopolymers bearing various alkyl chains was synthesized via a direct heteroarylation polymerization (DHAP) procedure. UV-visible absorption and powder X-ray diffraction measurements revealed the relationship between the ratio of branched to linear alkyl chains and the optoelectronic properties of the polymers as well as their packing in the solid state.
Solvent evaporation synthesis and crystal structure of tetra(thiophene-3,4-dicarboxylate)tetrahydrate
Zhu,Wang
, p. 1547 - 1548 (2015)
One new thiophene compound from 3,4-dibromothiophene, butyl lithium and anhydrous ether has been successfully synthesized. The compound has been characterized by X-ray single-crystal diffraction and shows a one-dimensional framework. The 3D supramolecular structure is formed via hydrogen bonding formation.
Preparation process 2-5 - thiophene dicarboxylic acid
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Paragraph 0030-0031; 0036-0038; 0043-0045; 0050-0051, (2021/12/07)
The invention relates to 2-5 - thiophene dicarboxylic acid preparation process comprising the following steps: preparing intermediate product 2 - aminothiophene -3, 4 -dicarboxylic acid 3 - ethyl ester 4 - methyl ester; and obtaining the final product 2 - and -3 thiophene dicarboxylic acid through the obtained intermediate product thiophene 4 - and 3 - 3 - dicarboxylic acid 4 - ethyl ester 4 -3 methyl ester, and finally obtaining the intermediate product thienothiophene 5 - 2 4 - 4 -3 diethyl 4 - carboxylate and 3 - methyl ethyl ester. The method disclosed by the invention is low in price, mild in reaction and high in yield, does not need to be purified by a silica gel column, and is very suitable for amplification production.
CRYSTAL FORMS OF THIOPHENE DERIVATIVES
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Paragraph 0273, (2021/05/14)
Disclosed is crystal form I of compound (S)—N-[5-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-4,6-dioxo-5,6-dihydro-4H-thieno[3,4-c]pyrrole-1-yl]acetamide.
From Red to Green Luminescence via Surface Functionalization. Effect of 2-(5-Mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4- c]pyrrole-4,6-dione Ligands on the Photoluminescence of Alloyed Ag-In-Zn-S Nanocrystals
Kowalik, Patrycja,Bujak, Piotr,Wróbel, Zbigniew,Penkala, Mateusz,Kotwica, Kamil,Maroń, Anna,Pron, Adam
supporting information, p. 14594 - 14604 (2020/10/09)
A semiconducting molecule containing a thiol anchor group, namely 2-(5-mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4-c]pyrrole-4,6-dione (abbreviated as D-A-D-SH), was designed, synthesized, and used as a ligand in nonstoichiometric quaternary nanocrystals of composition Ag1.0In3.1Zn1.0S4.0(S6.1) to give an inorganic/organic hybrid. Detailed NMR studies indicate that D-A-D-SH ligands are present in two coordination spheres in the organic part of the hybrid: (i) inner in which the ligand molecules form direct bonds with the nanocrystal surface and (ii) outer in which the ligand molecules do not form direct bonds with the inorganic core. Exchange of the initial ligands (stearic acid and 1-aminooctadecane) for D-A-D-SH induces a distinct change of the photoluminescence. Efficient red luminescence of nanocrystals capped with initial ligands (λmax = 720 nm, quantum yield = 67%) is totally quenched and green luminescence characteristic of the ligand appears (λmax = 508 nm, quantum yield = 10%). This change of the photoluminescence mechanism can be clarified by a combination of electrochemical and spectroscopic investigations. It can be demonstrated by cyclic voltammetry that new states appear in the hybrid as a consequence of D-A-D-SH binding to the nanocrystals surface. These states are located below the nanocrystal LUMO and above its HOMO, respectively. They are concurrent to deeper donor and acceptor states governing the red luminescence. As a result, energy transfer from the nanocrystal HOMO and LUMO levels to the ligand states takes place, leading to effective quenching of the red luminescence and appearance of the green one.
Single precursor for the synthesis of donor and acceptor units of the low band gap polymers: Synthesis of benzodithiophene and thienopyrroledione from maleic anhydride
Kadam, Vinay S.,Patel, Arun L.,Zade, Sanjio S.
supporting information, p. 2608 - 2611 (2016/06/01)
An efficient route was developed to synthesize dimethyl thiophene-3,4-dicarboxylate from maleic anhydride. Dimethyl thiophene-3,4-dicarboxylate was used as a single precursor for synthesis of benzo[1,2-b:4,5-b′]dithiophene (BDT) and Thieno[3,4-c]pyrrole-4,6-dione (TPD) derivatives. BDT and TPD derivatives have been highly exploited as donor and acceptor units, respectively, to synthesize important donor-acceptor (D-A) conjugated polymers. BDT-based polymers were found to be one of the most efficient conjugated polymers for organic photovoltaic application. Synthesis of quinone precursor of the dihydroxybenzothiophene was accomplished by a new and unconventional methodology which includes reaction of 3,4-thiophene dicarboxylate with sodium hydride in THF. Dithienobenzoquinone dicarboxylate and dihydroxybenzodithiophene dicarboxylate were characterized structurally by single-crystal X-ray diffraction. Both compounds show strong π-stacking interaction and arrange in the parallel molecular sheets in the crystals.
A versatile approach to organic photovoltaics evaluation using white light pulse and microwave conductivity
Saeki, Akinori,Yoshikawa, Saya,Tsuji, Masashi,Koizumi, Yoshiko,Ide, Marina,Vijayakumar, Chakkooth,Seki, Shu
supporting information, p. 19035 - 19042 (2013/01/15)
State-of-the-art low band gap conjugated polymers have been investigated for application in organic photovoltaic cells (OPVs) to achieve efficient conversion of the wide spectrum of sunlight into electricity. A remarkable improvement in power conversion efficiency (PCE) has been achieved through the use of innovative materials and device structures. However, a reliable technique for the rapid screening of the materials and processes is a prerequisite toward faster development in this area. Here we report the realization of such a versatile evaluation technique for bulk heterojunction OPVs by the combination of time-resolved microwave conductivity (TRMC) and submicrosecond white light pulse from a Xe-flash lamp. Xe-flash TRMC allows examination of the OPV active layer without requiring fabrication of the actual device. The transient photoconductivity maxima, involving information on generation efficiency, mobility, and lifetime of charge carriers in four well-known low band gap polymers blended with phenyl-C61-butyric acid methyl ester (PCBM), were confirmed to universally correlate with the PCE divided by the open circuit voltage (PCE/Voc), offering a facile way to predict photovoltaic performance without device fabrication.
THIOPHENE DERIVATIVES
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Page/Page column 25, (2012/04/17)
Disclosed is a compound of formula (1), wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the present application.
Improved synthesis of thienothiazole and its utility in developing polymers for photovoltaics
Uy, Rycel,Yang, Liqiang,Zhou, Huaxing,Price, Samuel C.,You, Wei
body text, p. 9146 - 9154 (2012/06/16)
In response to the structural and electronic limitations of the popular benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-b]thiophene (PBnDT-TT) polymer series, this study explores the design and synthesis of a thienothiazole (TTz) moiety. The synthesis of TTz was streamlined down to four high-yielding steps, resulting in the new polymer PBnDT-TTz for organic solar cells. By incorporating TTz, a nitrogen is directly introduced into the polymer backbone which tunes the HOMO level and eliminates the reliance on external substituents. Compared to its TT analogue, PBnDT-TTz exhibits the same HOMO level of -5.06 eV and the same Voc of 0.69 eV, yet a higher power conversion efficiency of 2.5%. These promising results demonstrate the benefits of backbone modification and the great potential of TTz in the design of new polymers for organic photovoltaics.
DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
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, (2010/05/13)
The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
