1504-39-8Relevant academic research and scientific papers
Dissymmetrical photodimerization of methyl 9-anthroate
Noh, Taehee,Lim, Heejun
, p. 495 - 496 (1997)
Irradiation of methyl 9-anthroate through a Uranium filter gave the 1,4-10′,9′ and 1,4-9′,10′ cyclodimers as well as the 9,10-10′,9′ cyclodimer, this is the first example of intermolecular photodimerization involving the 1, 4, 9′, and 10′ positions of meso-substituted anthracenes. These dissymmetrical cyclodimers were found to be thermally more labile than the 9,10-10′,9′ cyclodimer.
Solvent modulated photophysics of 9-methyl anthroate: Exploring the effect of polarity and hydrogen bonding on the emissive state
Ganguly, Aniruddha,Jana, Sankar,Ghosh, Soumen,Dalapati, Sasanka,Guchhait, Nikhil
, p. 237 - 244 (2013)
Photophysical properties of an anthracene derivative 9-methyl anthroate (9-MA) have been investigated using absorption and emission spectroscopy, in combination with quantum chemical calculations. Solvatochromic effects on the Stokes shifted emission band clearly demonstrate the highly polar character of the excited state, which is also supported by the enhancement of dipole moment of the molecule upon photoexcitation. The emission band has been found to be dependent on polarity and hydrogen-bonding ability of the solvents. Multiple linear regression analysis method has been utilized to rationalize the effect of hydrogen bonding interaction on the emissive state, which was further confirmed by the analysis of the non-radiative decay constants and urea induced H-bonding disruption study. The experimental results correlate well with theoretical predictions obtained via density functional theory (DFT).
Low-Temperature Emission Spectra of 9-Alkylanthracene Esters: Dimer Photodecomposition and Monomer Pair Interactions in Polymer Hosts
Salt, Kimberly,Scott, Gary W.
, p. 9986 - 9991 (1994)
Effects due to variation in the alkyl chain length of photodimers of 9-alkylanthracene esters on their photodecomposition efficiencies at 12 K and, by implication, the photoproduct migration as a function of temperature within polymer hosts are investigated.It is shown that dimers with longer alkyl chains have a lower photodecomposition efficiency.The extent of photoproduct migration within the polymer following photodecomposition was also studied as a function of alkyl chain length.This migration and its modulation of the interaction between the separating monomers is shown to affect the emission spectrum.Thus, monomer migration was studied in temperature cycling experiments.It was also found, for the polymer hosts investigated - poly(methyl methacrylate), poly(vinyl chloride), and polystyrene - that these properties are host dependent.This result is probably due to the void space differences that exist among these polymers.
A non-steroidal facial amphiphile
Menger, Fredric M.,Sorrells, Jennifer L.
, p. 4960 - 4961 (2006)
This paper gives the synthesis of an unusual non-steroidal amphiphile consisting of a large rigid molecule that possesses two water-solubilizing sulfates on one face and an extended hydrophobic surface on the other. The properties of this compound have been examined by X-ray analysis, light and cryo-electron microscopy, surface tension, conductivity, microrheology, and NMR. Aqueous solutions behave quite differently from those of a conventional amphiphile with long linear and flexible chains (e.g., sodium dodecyl sulfate). Thus, there is evidence that the facial amphiphile self-assembles to form viscous networks, but without the traditional critical micelle concentration, as if assembly is a stepwise process. Emulsions of toluene in water promoted by the facial amphiphile are stable for many months. In contrast to conventional surfactants, the NMR peaks are obliterated in aqueous solutions of the facial amphiphile. Both X-ray and cryo-HRSEM data suggest a lamellar morphology. Copyright
A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides
Bartling, Stephan,Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Rabeah, Jabor,Rockstroh, Nils,Senthamarai, Thirusangumurugan
supporting information, p. 508 - 531 (2022/02/11)
Functionalized (hetero)aromatic compounds are indispensable chemicals widely used in basic and applied sciences. Among these, especially aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides represent valuable fine and bulk chemicals, which are used in chemical, pharmaceutical, agrochemical, and material industries. For their synthesis, catalytic aerobic oxidation of alcohols constitutes a green, sustainable, and cost-effective process, which should ideally make use of active and selective 3D metals. Here, we report the preparation of graphitic layers encapsulated in Co-nanoparticles by pyrolysis of cobalt-piperazine-tartaric acid complex on carbon as a most general oxidation catalyst. This unique material allows for the synthesis of simple, functionalized, and structurally diverse (hetero)aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides from alcohols in excellent yields in the presence of air.
Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions
Ishida, Takumi,Nishihara, Yasushi,Wang, Xiu,Wang, Zhenhua
, p. 7526 - 7533 (2020/06/27)
Acyl fluorides are subjected to methoxylation with tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) to afford the corresponding methyl esters in good to excellent yields. This transformation is featured by C(sp2)-OMe bond cleavage under metal-free conditions. Unprecedented utilization of TMPP as a methoxylating agent realized the installation of an OMe group into the desired products.
Pd-Colloids-Catalyzed/Ag2O-Oxidized General and Selective Esterification of Benzylic Alcohols
Sable, Vaibhav,Shah, Jagrut,Sharma, Anuja,Kapdi, Anant R.
supporting information, p. 2639 - 2647 (2019/07/08)
Palladium colloids obtained from the degradation of Hermann–Beller palladacycle proved to be an efficient catalytic system in combination with silver oxide as a selective oxidant for the oxidative esterification of differently substituted benzyl alcohols in MeOH as solvent. Excellent reactivity exhibited by the catalytic system also allowed the alcoholic coupling partner to be changed from MeOH to a wide range of alcohols having diverse functionalities. The mildness of the developed protocol also made it possible to employ propargyl alcohol as the coupling partner without any observation of any interference of the terminal alkyne. Selective oxidative coupling of a primary alcoholic functional group over secondary in the case of glycols and glycerols was also made possible using the developed catalyst system. To test the relevancy of Pd/Ag combined catalysis mixed Pd/Ag colloids were synthesized, characterized by TEM, XRD and XPS and applied to oxidative-esterification successfully.
Copper-catalyzed methyl esterification reactions via C-C bond cleavage
Zhu, Yan,Yan, Hong,Lu, Linhua,Liu, Defu,Rong, Guangwei,Mao, Jincheng
, p. 9898 - 9905 (2013/10/22)
The highly effective synthesis of methyl esters from benzylic alcohols, aldehydes, or acids via copper-catalyzed C-C cleavage from tert-butyl hydroperoxide is reported in this paper for the first time. Our protocol is easily accessible and practical, making it a possible supplement for the traditional way.
Solid-state photochemical and photomechanical properties of molecular crystal nanorods composed of anthracene ester derivatives
Zhu, Lingyan,Agarwal, Arun,Lai, Jinfeng,Al-Kaysi, Rabih O.,Tham, Fook S.,Ghaddar, Tarek,Mueller, Leonard,Bardeen, Christopher J.
experimental part, p. 6258 - 6268 (2011/11/12)
A series of 9-anthroate esters that can form photoresponsive molecular crystal nanorods is prepared and their properties are investigated. All crystal structures that can support a [4 + 4] photodimerization reaction lead to nanorods that undergo photomechanical deformations without fragmentation. In order to determine the molecular-level motions that give rise to the nanorod photomechanical response, the reaction of anthracene-9-carboxylic acid tert-butyl ester is studied in detail using X-ray diffraction and solid-state NMR techniques. The monomer crystal is well-aligned within the nanorod and reacts to form the photodimer crystal according to first-order kinetics. The solid-state reacted dimer crystal is a metastable intermediate that slowly converts into the low energy dimer crystal structure over the course of weeks. Based on single crystal X-ray diffraction studies and solid-state NMR data, this intermediate structure is likely composed of the [4 + 4] photodimer that has not yet undergone the ester group rotations and repacking is necessary to form the lower energy crystal polymorph that is produced directly by crystallization from solution. Our results show that the photomechanical response of these molecular crystal nanostructures is determined by nonequilibrium intermediate states and cannot be predicted based solely on knowledge of the equilibrium reactant and product crystal structures.
Reductions of challenging organic substrates by a nickel complex of a noninnocent crown carbene ligand
Findlay, Neil J.,Park, Stuart R.,Schoenebeck, Franziska,Cahard, Elise,Zhou, Sheng-Ze,Berlouis, Leonard E. A.,Spicer, Mark D.,Tuttle, Tell,Murphy, John A.
supporting information; experimental part, p. 15462 - 15464 (2011/02/22)
The first crown-tetracarbene complex of Ni(II) has been prepared, and its crystal structure determined. The complex can be reduced by Na/Hg, with an uptake of two electrons. The reduced complex reductively cleaves arenesulfonamides, including those derived from secondary aliphatic amines, and effects Birch reduction of anthracenes as well as reductive cleavage of stilbene oxides. Computational studies show that the orbital that receives electrons upon reduction of the complex 2 is predominantly based on the crown carbene ligand and also that the HOMO of the parent complex 2 is based on the ligand.
