174848-08-9Relevant articles and documents
Vicarious Substitution of Hydrogen in Aromatic Nitro Compounds with Acetonitrile Derivatives
Makosza, Mieczyslaw,Winiarski, Jerzy
, p. 1534 - 1535 (1980)
Carbanions of α-phenoxy and thioalkoxy nitriles substitute hydrogen in the para or ortho position of aromatic nitro compounds, giving nitroarylacetonitriles in a process in which phenolate or thiolate anions are vicarious leaving groups.
An A-D-A small molecule based on the 3,6-dithienylcarbazole electron donor (D) unit and nitrophenyl acrylonitrile electron acceptor (A) units for solution processed organic solar cells
Singh, Manjeet,Kurchania, Rajnish,Mikroyannidis,Sharma,Sharma
, p. 2297 - 2306 (2013)
A new A-D-A small molecule (SM) based on a 3,6-dithienylcarbazole donor unit at the center and nitrophenyl acrylonitrile acceptor units as the terminal ends was synthesized by the Pd catalyzed Stille coupling reaction for application as a donor material in the organic bulk heterojunction solar cells. The SM possesses a low lying HOMO energy level at -5.34 eV and optical band gap of 1.74 eV. The photovoltaic performance of the SM was investigated with PC 60BM and PC70BM as acceptors cast from THF with 3% CN additive and without additive. The power conversion efficiency (PCE) of the organic solar cells based on SM:PC60BM cast from THF solvent reached 1.94% with a high Voc of 0.94 V, a Jsc of 6.08 mA cm -2 and FF of 0.34, where as the PCE of SM:PC70BM cast from THF solvent was 2.65% with a Voc of 0.96 V, a Jsc of 7.26 mA cm-2 and FF of 0.38%, under the illumination intensity of 100 mW cm-2. The higher PCE of the organic solar cells based on PC 70BM as an electron acceptor has been attributed to its strong absorption in the visible region than PC60BM. The PCE of the organic solar cells has been further improved to 3.76% and 4.96% for SM:PC 60BM and SM:PC70BM, respectively, cast with CN-THF solvent. The Royal Society of Chemistry 2013.
Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties
Gualandi, Andrea,Nenov, Artur,Marchini, Marianna,Rodeghiero, Giacomo,Conti, Irene,Paltanin, Ettore,Balletti, Matteo,Ceroni, Paola,Garavelli, Marco,Cozzi, Pier Giorgio
, p. 981 - 989 (2020/12/07)
High level time-dependent density functional theory (TD-DFT) computational modeling of coumarin dyes has been exploited for guiding the design of effective photocatalysts (PCs). A library of coumarins were investigated from the theoretical point of view and photophysical/electrochemical properties (absorption and emission spectra, E00, oxidation and reduction potentials) were evaluated. Comparison with literature values reported for a few candidates has been used for assessing the level of theory. On the basis of the results obtained, new strongly reducing PCs [Eox(PC.+/PC*)=?2.1 – ?2.0 V vs SCE] were discovered. Through the computational study of structure-properties relationships, a number of coumarins derivatives have been synthesized and evaluated in the pinacol coupling of aldehydes as the model reaction. The new organic photoredox catalysts show experimental photophysical and electrochemical data in accordance with the ones predicted by calculation, with excited state reduction potentials surpassing those of highly reducing transition metal-based PCs. A careful investigation of their behavior as PC has revealed crucial issues that need to be taken into consideration in the general photoredox catalysis, shedding light on the use of these PC in the pinacol, as well as, in other photoredox reactions.
Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles
Al-Huniti, Mohammed H.,Rivera-Chávez, José,Colón, Katsuya L.,Stanley, Jarrod L.,Burdette, Joanna E.,Pearce, Cedric J.,Oberlies, Nicholas H.,Croatt, Mitchell P.
, p. 6046 - 6050 (2018/09/27)
A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.
