30711-41-2Relevant articles and documents
Mono-ketone modified C60s for acceptor materials in organic photovoltaic cells
Lee, Hak Sung,Yoon, Sung Cheol,Lim, Jongsun,Lee, Myongsoo,Lee, Changjin
, p. 293 - 302 (2008)
We designed and synthesized methanofullerene derivatives with several types of thiophenyl mono-ketone for application in organic photovoltaic cells (OPVCs) as new accepter materials. The various mono-ketones having thiophene rings were substituted onto fullerene through application of Hirch-Bingel reaction under mild condition to compete with donor materials especially P3HT [Poly(3-hexylthiophene)] for nano-networking bulk-heterojunction structure where efficient light-induced charge separation is enable by a large-area donor-acceptor interface. The newly synthesized methanofullerene derivatives were characterized through 1H-NMR and FAB Mass spectroscopy. The compounds were also applied in OPV cell devices with P3HT as a donor material and measured electrochemical the property and power conversion efficiency.
A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects
Ghinato, Simone,Territo, Davide,Maranzana, Andrea,Capriati, Vito,Blangetti, Marco,Prandi, Cristina
, p. 2868 - 2874 (2021/01/21)
We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.
Iron(III)-Catalyzed Hydration of Unactivated Internal Alkynes in Weak Acidic Medium, under Lewis Acid-Assisted Br?nsted Acid Catalysis
Antenucci, Achille,Flamini, Piergiorgio,Fornaiolo, Marco Valerio,Di Silvio, Sergio,Mazzetti, Sara,Mencarelli, Paolo,Salvio, Riccardo,Bassetti, Mauro
, p. 4517 - 4526 (2019/08/26)
Alkylarylalkynes are converted with full regioselectivity into the corresponding arylketones by formal hydration of the triple bond under weak acidic conditions, at times and temperatures (≤95 °C) comparable to those used for terminal alkynes. The process catalyzed by Fe2(SO4)3nH2O in glacial acetic acid exhibits good functional group compatibility, including that with bulky triple bond substituents, and can be extended to the one-pot transformation of aryltrimethylsilylacetylenes into acetyl derivatives via a desilylation-hydration sequence. The overall reactivity pattern along with proton affinity data indicate that the triple bond is activated by proton transfer rather than by π-interaction with the metal ion. This mechanistic feature, at variance with that of noble metal catalysts, accounts for the total regioselectivity and the insensitivity to steric hindrance exhibited by the Fe2(SO4)3nH2O/AcOH catalytic system. (Figure presented.).
Synthesis of 1,3,6,8-tetra-substituted pyrene derivatives and application of pyrene derivatives in organic field-effect transistors
-
Paragraph 0013; 0017; 0018, (2019/10/01)
The invention aims to develop synthesis of 1,3,6,8-tetra-substituted pyrene derivatives of the same category having semiconductor properties and application of the derivatives in organic field-effecttransistors. Series thiophene units are introduced into positions 1, 3, 6 and 8 of pyrene to construct the tetra-substituted pyrene derivatives, and material preparation is performed by utilizing a chemical reaction. Moreover, a silicon wafer serves as a gate, and the pyrene derivatives serve as organic semiconductor materials, so that bottom-gate top-contact field-effect transistors are prepared.R refers to the following groups as shown in the specification.
New approach to the synthesis of 2,2':5',2''-terthiophene-5,5''-and 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids
Kostyuchenko, Anastasia S.,Ulyankin, Evgeny B.,Shatsauskas, Anton L.,Shuvalov, Vladislav Yu.,Fisyuk, Alexander S.
, p. 1026 - 1032 (2019/01/04)
[Figure not available: see fulltext.] The reaction of bromosuccinimide with esters of 3-substituted 2,2'-bithiophene-5-carboxylic acids was used to obtain their 5'-bromo derivatives, which were further converted to esters of 3,3'''-disubstituted 2,2':5',2
1,8-Substituted Pyrene Derivatives for High-Performance Organic Field-Effect Transistors
Gong, Xiaojie,Zheng, Chaoyue,Feng, Xingcui,Huan, Yihong,Li, Jiewei,Yi, Mingdong,Fu, Zhenqian,Huang, Wei,Gao, Deqing
supporting information, p. 3920 - 3927 (2018/11/23)
There have been many reports on the application of pyrene derivatives as organic semiconductors, but 1,8-subsituted pyrene semiconductors are less well-developed. Two p-type 1,8-substituted pyrene derivatives were synthesized that were composed of a pyrene core, thiophene or bithiophene arms, and end-capped octyl chains. These structures were not completely symmetrical and the dihedral angles between the pyrene core and the adjacent thiophene units had a difference of approximately two degrees. The field-effect performance of these materials was tested on a variety of dielectric surfaces. The performance of both materials with a spin-coated polystyrene layer on SiO2 (PS-treated SiO2) was better than that with an octadecyltrichlorosilane self-assembled monolayer on SiO2 (OTS-treated SiO2), which was mainly attributed to the presence of large grains on the low-leakage and high-capacitance PS films. The thiophene-contained compound presented a hole mobility of up to 0.18 cm2 V?1 s?1 on PS-treated SiO2, which was 45 times that of the bithiophene-contained compound, owing to less steric hindrance, high crystallinity, and large grain size.
A simple and efficient synthesis of substituted 2,2′-bithiophene and 2,2′:5′,2″-terthiophene
Kostyuchenko, Anastasia S.,Averkov, Alexey M.,Fisyuk, Alexander S.
supporting information, p. 1833 - 1835 (2014/05/06)
A simple and efficient approach is developed for the synthesis of substituted 2,2′-bithiophene- and 2,2′:5′,2″- terthiophene-5-carboxylic acids and esters which is based on thiophene ring closure in the Fiesselmann reaction. Using this method, derivatives containing a long alkyl chain with or without an end functional group or an aryl substituent can be conveniently prepared.
Palladium(0) nanoparticle-catalyzed sp2 C-H activation: A convenient route to alkyl-aryl ketones by direct acylation of aryl bromides and iodides with aldehydes
Adak, Laksmikanta,Bhadra, Sukalyan,Ranu, Brindaban C.
experimental part, p. 3811 - 3814 (2010/08/19)
Palladium(0) nanoparticles efficiently catalyze aliphatic aldehyde C-H functionalization by aryl halides to produce alkyl-aryl ketones in good yields. A wide range of substituted aryl and hetero-aryl bromides/iodides and open-chain aldehydes of varied chain length participated in this reaction.
Synthesis, polymerization and characterization of substituted dithieno [3,4-b: 3',4'-d] thiophenes
Inaoka, Seiji,Collard, David M.
, p. 1719 - 1725 (2007/10/03)
Chemical or electrochemical oxidation of substituted dithieno [3,4- b:3',4'-d]thiophenes provides polymers with defined regiochemical structures. These materials have lower bandgaps (0.7-0.9 eV) than the unsubstituted fused heteroarene. Potential cycling of the 1,3-dimethyl substituted polymer film shows repetitive p- and n-dopability. The chemically-prepared dioctyl analog is soluble in common solvents such as chloroform, dichloromethane and THF. However, overoxidation of the polymers at an electrode surface presents a limitation to the polymerization of substituted analogs of the parent fused heteroarene.
