5736-88-9Relevant articles and documents
Tuning the SOCT-ISC of bodipy based photosentizers by introducing different electron donating groups and its application in triplet-triplet-annihilation upconversion
Liang, Hui,Sun, Shanshan,Zafar, Mahmood,Yuan, Zhanxiang,Dong, Yuye,Ji, Shaomin,Huo, Yanping,Li, Ming-De,Zhao, Jianzhang
, (2020)
To study the effect of electron-donating ability on spin orbit charge transfer intersystem crossing (SOCT-ISC) efficiency, a series of bodipy derivatives (BDP-O, BDP-2-MN, BDP-2-EN) linked with electron-donating groups with different electron-donor abilities were synthesized. For BDP-2-MN and BDP-2-EN, both compounds show a sharp charge transfer emission band at 630 nm, and the local excited (LE) emission in both compounds were completely quenched due to photo-induced electron transfer (PET). By femtosecond transient absorption measurement, the triplet state population in both compounds was confirmed to occur through charge recombination (1996 ps ~2307 ps) process after the photo-induced electron transfer upon photoexcitation of bodipy moiety. A long-lived triplet excited state was observed for both compounds (lifetimes: 37 ~ 42 μs) via nanosecond transient absorption. The BDP-2-MN and BDP-2-EN can act as the triplet photosensitizers without heavy elements for the application of triplet-triplet-annihilation upconversion (TTA-UC, ΦUC can reach 4.88%). In case of BDP-O molecule, no triplet signal was observed for this compound because of poor electronic coupling between donor and acceptor. Therefore, the triplet excited state properties of bodipy chromophore was successfully regulated by adjusting electronic strength of donor moiety and implement these photosensitizers in the application of TTA-UC.
Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes
Liu, Shuai,Liu, Zhong-Quan,Shen, Tong,Shen, Xu,Wang, Nengyong,Wu, Jintao,Yang, Le,Zhao, Jianyou
, p. 3286 - 3295 (2022/03/14)
An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.
Novel N-heterocyclic carbene cyclic palladium compound as well as preparation method and application thereof
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Paragraph 0027; 0031; 0034, (2021/06/26)
The invention discloses a novel N-heterocyclic carbene cyclic palladium compound as well as a preparation method and application thereof, and belongs to the technical field of organic catalysis. The novel N-heterocyclic carbene cyclic palladium compound is prepared by the following steps: heating, stirring and mixing N-(4-butoxybenzyl)-N-ethylethylamine, palladium chloride and an organic solvent in an inert gas atmosphere, then adding potassium carbonate, performing stirring and mixing, and finally adding 1-(2,6-diisopropyl phenyl)-3-butyl-brominated imidazole for reflux reaction; and after the reaction is finished, performing quenching with an acid solution, performing extracting to obtain a crude product, and performing column chromatography separation and purification to obtain the novel N-heterocyclic carbene cyclic palladium compound. The N-heterocyclic carbene cyclic palladium compound provided by the invention has high catalytic activity, can catalyze cross-coupling reactions between aryl chloride and aryl phenylboronic acid and between aryl chloride and secondary amine in a catalytic amount of 1 mol%, and can be used as a high-efficiency catalyst for the coupling reactions.
Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones
Banerjee, Prabal,Maajid Taily, Irshad,Saha, Debarshi
supporting information, p. 5053 - 5057 (2021/09/30)
An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained Csp3?Csp3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.
1,3-Oxazine-2-one derived dual-targeted molecules against replicating and non-replicating forms of Mycobacterium tuberculosis
Velappan, Anand Babu,Kesamsetty, Dhanunjaya,Datta, Dhrubajyoti,Ma, Rui,Hari, Natarajan,Franzblau, Scott G.,Debnath, Joy
supporting information, (2020/10/02)
The high mortality rate and increasing prevalence of resistant Mtb are the major concerns for the Tuberculosis (TB) treatment in this century. To curtail the prevalence of resistant Mtb, we have prepared 1,3-oxazine-2-one based dual targeted molecules. Compound 67 and 68 were found to be equally active against replicating and non-replicatiing form of Mtb (MICMABA 3.48 and 2.97 μg/ml; MICLORA 2.94 and 2.15 μg/ml respectively). They had found to suppress the biosynthesis of alfa, methoxy and keto-mycolate completely, as well as inhibit enzymatic activity of MenG (IC50 = 9.11 and 6.25 μg/ml respectively for H37Ra; IC50 = 11.76 and 10.88 μg/ml respectively for M smegmatis).
Synthesis and mesomorphic properties of coumarin derivatives with chalcone and imine linkages
Durgapal, Sunil Dutt,Soni, Rina,Soman, Shubhangi S.,Prajapati
, (2019/11/26)
We report here design and synthesis of two new mesogenic homologous series of coumarin derivatives consisting of chalcone and imine central linkages along with terminal n-alkoxy chain. All the compounds were synthesized and characterized by combination of elemental analysis and standard spectroscopic methods. All compounds were screened under polarising optical microscope (POM) for liquid crystalline properties, thermogram of all compounds were studied using differential scanning calorimetry (DSC) to get phase transition temperatures, enthalpy and entropy. X-ray single crystal study of n-octyloxy coumarin derivative 16 g was resolved with imine central linkage, which showed linear rod like geometry.
Anticancer, antimicrobial activities of quinoline based hydrazone analogues: Synthesis, characterization and molecular docking
Katariya, Kanubhai D,Shah, Shailesh R.,Reddy, Dushyanth
supporting information, (2019/11/26)
Based on the biologically active heterocycle quinoline, a series (18a-p) of quinoline hydrazone analogues were prepared, starting from 6-bromo/6-chloro-2-methyl-quinolin-4-yl-hydrazines. For all the newly synthesized compounds cytotoxic activities were carried out at the National Cancer Institute (NCI), USA, against full NCI 60 human cancer cell lines. Amongst all the tested compounds, nine compounds (18b, 18d, 18e, 18f, 18g, 18h, 18i, 18j, 18l) exhibited important anti-proliferative activity at 10 μM concentration and were further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 μM) with GI50 values ranging from 0.33 to 4.87 μM and LC50 values ranging from 4.67 μM to >100j μM. Further, the mean values of GI50, TGI and LC50 of the most potent compound 18j were compared with the clinically used anticancer agents bendamustine and chlorambucil, revealed that the quinolyl hydrazones holds promise as a potential anticancer agents. Further all the newly prepared compounds were screened for their antimicrobial activity. All the quinolyl hydrazones displayed good to excellent antimicrobial activity with MIC values ranging from 6.25 to 100 μg/mL against the tested pathogenic strains. Molecular docking of the synthesized compounds into the active binding site of human DNA topoisomerase I (htopoI) was carried out to predict the binding mode to the DNA topoisomerase I inhibitors. Hopefully in future, compounds based on quinoline core could be used as a lead compounds for designing new anticancer agents.
2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms
Datta, Dhrubajyoti,Debnath, Joy,Franzblau, Scott G.,Ghosh, Kalyan Sundar,Hari, Natarajan,Ma, Rui,Rana, Shiwani,Velappan, Anand Babu
, (2020/09/04)
The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 μg/ml; MIC(LORA) 2.06 and 1.59 μg/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 μM respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 μM respectively) followed by the Vit-K2 rescue study and ATP production assay.
Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex
Cao, Rui,Lai, Chu-Hui,Li, Gang,Liu, Fengyi,Lu, Huan-Huan,Wang, Chao,Xiao, Jianliang,Xue, Dong,Yang, Liu,Zhang, Wei
supporting information, p. 12714 - 12719 (2020/06/02)
A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.
Porphyrin molecule for fluorenyl Friedel-Crafts reaction modification, post-modification material, preparation method and application thereof
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Paragraph 0059; 0061; 0062, (2019/11/19)
The invention discloses a porphyrin molecule for fluorenyl Friedel-Crafts reaction modification, a post-modification material, a preparation method and application thereof. The method for functional modification of porphyrin molecule by Friedel-Crafts reaction introduces porphyrin ring into a conjugate interrupted steric hindrance group molecule, advantageously destroys the pi-pi effect between faces, effectively regulates the energy level structure and realizes functional modification. The synthetic strategy of Friedel-Crafts reaction provided by the invention is green and environment-friendly, has low loss and high yield, is simple in operation and low in cost, and is a new porphyrin functional modification method that can be popularized and applied. The porphyrin Friedel-Crafts post-modified structural molecule designed and synthesized by the invention is a functional photoelectric information material, can be applied to a memristor active layer for functional simulation of an artificial neural network, and is expected to provide new possibility for application of organic memristor materials.
