Latest ArticlesThe isoindolinone and biaryl scaffolds are prevalent in natural products and drug molecules, which have showed broad and interesting biological activities. The efficient construction of such hybridized molecules and biological evaluation are of great interest to medicinal chemistry community. In this communication, we report an efficient Brønsted acid-promoted C(sp3)-H functionalization approach that enables the rapid construction of biologically important isoindolinone/[1,2,4]triazolo[1, 5-a]pyrimidine hybrids from 5-methyl-7-(2, 4, 6-trimethoxyphenyl)-[1,2,4]triazolo[1, 5-a]pyrimidine, 2-formylbenzoic acid and various anilines. The title compounds were generated in high to excellent yields (up to 96%) regardless of the electronic nature and steric effects of the substituents. In this reaction, an isoindolinone scaffold, one C-C single bond, and two C-N bonds were formed simultaneously with high atom economy. In this work, we have envisioned that the methyl group linked to the electron-deficient Nheterocycles could be used as a new synthetic handle for late-state diversification and may have broad applications in the field of organic and medicinal chemistry. Besides, the title compounds have exhibited promising activity against the SKP2-CKS1 interaction.
A new star-shaped molecule StOF-Br3 containing oligofluorenes and halogen atoms (Bromine) has been synthesized and studied by Scanning Tunneling Microscopy (STM) at the highly oriented pyrolytic graphite (HOPG) surface. We have obtained the high-resolution self-assembled STM images, from which the highly ordered and closely packed non-porous arrangements of the StOF-Br3 molecular selfassemblies at the heptanoic acid/HOPG surface could be observed. The molecular models and selfassembled StOF-Br3 architectures have been given in the following text. Besides, we have also figured out the surface free energy by the density functional theory (DFT) calculation, which proved that the halogen···halogen interaction was strong enough to stabilize the ordered molecular self-assemblies. This work verifies the existence of bromine···bromine interactions, and meanwhile provides a kind of effective approach for quickly building ordered molecular nanoarchitectures with large areas and different geometries.
A range of bench-stable carbazole-containing hypervalent iodine(Ⅲ) reagents were synthesized by I-N bond formation in good yields. This kind of benziodoxolone reagents was used for a C-N coupling reaction to introduce a carbazole group to aromatic heterocycle compounds.
Aggregation-induced emission (AIE) active photochromic molecules have attracted growing attention for their versatile applications. Here we designed and synthesized five newly unsymmetrical photochromic diarylethene (DAE) dyads (BTE1-5) by connecting tetraphenylethene (TPE) and aromatic substituent via bithienylethene (BTE) bridge. The chemical structures of those compounds were identified by 1H NMR, 13C NMR and HRMS.The absorption and emission of these dyads were investigated by UV-vis and fluorescence spectroscopy, respectively. The results showed that all those compounds exhibited typically AIE or aggregation-induced emission enhancement (AIEE) characteristic. Particularly, when an aggregation caused quenching (ACQ) fluorophore (triphenylamine) was grafted to the molecule, connecting with TPE via BTE-bridge, the ACQ phenomenon was dissipated and converted to an AIE luminophore, and those compounds exhibited photochromism upon irradiation with alternative UV and visible light. The solution or solid of those compounds showed distinctly fluorescence switching "ON" or "OFF" observation upon irradiation with alternative UV and visible light.It is interesting that BTE1 could be applied in recording and rewritable information storage, and the cyclization quantum yields could be affected by substituent significantly.
Polylactic acid (PLA) is one of the most suitable candidates for environmental pollution treatment because of its biodegradability which will not cause secondary pollution to the environment after application. However, there is still a lack of a green and facile way to prepare PLA oil-water separation materials. In this work, a water-assisted thermally induced phase separation method for the preparation of superhydrophobic PLA oil-water separation material with honeycomb-like structures is reported. The PLA material shows great ability in application and could adsorb 27.3 times oil to its own weight. In addition, it could also be applicated as a filter with excellent efficiency (50.9 m3 m-2 h-1).
Host-guest supramolecular gels were developed via the self-assembly of inclusion complexes (ICs) of β-cyclodextrins/phenylboronic acid gelator (PBA). Salts and current were involved in the self-assembly to stabilize the host-guest gels. The stability of the gels was greatly improved after salts were added. The stable time of gels was extended from 2.5 h to 120 h with the addition of NH4NO3 at the concentration of 2.5×10-2 g/mL. The morphology of the gel was affected by the concentrations of NH4NO3. SEM images revealed that the gels were three-dimensional nanofibrous networks, the sizes of fibers decreased with decreasing NH4NO3 concentrations, which affected the stability of gels, further proved by the rheological properties of gels. More stable gels were obtained with current stimulation, the stable time of the gel was increased from 2.5 h to 55 h with current by adding NaBF4. The current also exhibited significant influence on the aggregation as the voltage varied (0-500 mV) with a constant concentration of salts. The result showed the self-assembly process of host-guest gel could be well controlled via the addition of salts and current to desired morphology and stability.
A new silver mediated aminophosphinoylation of propargyl alcohols with aromatic amines and Hphosphine oxides for the construction of α-aminophosphine oxides has been developed. The C-N and C-P bond could be efficiently formed in one pot operation via sequential C-C and C-O bond cleavage of propargylic alcohols. This present methodology, which not only provides a simple and alternative strategy for the synthesis of α-aminophosphine oxides, but also opens a new window for the cleavage reactions of propargyl alcohols via dealkynalation coupling.
An organocatalytic asymmetric [3+2] cycloaddition of trifluoromethyl-containing azomethine ylides with cyclic 2, 4-dienones was developed. The process enables efficient incorporation of CF3 groups into functionalized spiro[pyrrolidin-3, 2'-oxindoles] in high yields with good to excellent enantio-and diastereoselectivities.
A quinine-derived thiourea-catalyzed inter-/intramolecular Michael cycloaddition of chromoneoxindole/benzofuranone synthons with 3-substituted methylenebenzofuranones has been established, which constructed enantiomerically pure bispiro[benzofuran-oxindole/benzofuran-chromanone]s bearing five consecutive stereocenters including two spiro quaternary carton centers in good yields (up to 93%) with high diastereoselectivities (up to >20:1 dr) and good enantioselectivities (up to >99% ee). Moreover, this is the first example of bifunctional chromone-benzofuranone synthon directed organocatalytic tandem reaction, and also the first example of the bispiro[benzofuran-oxindole] and bispirobenzofuranone, potentially useful in medicinal chemistry.
A heteropore covalent organic framework (COF) integrating tetraphenylethene skeleton and catechol segment is designed and synthesized. It exhibits extremely high stability in water under different pH conditions, which makes it an excellent material for adsorptive removal of Cd(Ⅱ) from aqueous solutions with very fast adsorption kinetics, high uptake capacity, and good recyclability.
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