Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides.

Here, we report a novel and facile protocol for the synthesis of benz[c,d]indol-2-imines via palladium-catalyzed C-C and C-N coupling of 8-halo-1-naphthylamines with isocyanides in a single step. The reaction features broad substrate scopes and mild conditions, providing an efficient alternative for the construction of antiproliferative agents and BET bromodomain inhibitors. If 0.1 mL of H2O was added to this reaction, the N-substituted amino-1-naphthylamides could be obtained easily.

Copper-catalyzed construction of (Z)-benzo[cd]indoles: stereoselective intramolecular trans-addition and SN-Ar reaction.

Substituted benzo[cd]indoles are one of the most attractive frameworks because of their wide range of biological and optical activities. Herein, a copper-catalyzed one-step synthesis of biologically important polysubstituted benzo[cd]indoles starting from 8-alkynyl-1-naphthylamine derivatives is reported. In this protocol, many substituents tolerated the reaction conditions and produced (Z)-benzo[cd]indoles in good yields. Preliminary mechanistic studies indicated that the reaction proceeds via a stereoselective intramolecular trans-addition and SN-Ar reaction with high selectivity and high yields. The synthesized polysubstituted (Z)-benzo[cd]indoles possess sulfonamide building blocks, which make them candidates for bioactive molecules.

Ratiometric fluorescent probe with AIE characteristics for hypochlorite detection and biological imaging.

It is very important and highly valuable to detect ClO- in samples and living cells with accuracy and speed. In this work, a novel fluorescent probe NA was prepared from 4-bromo-1,8-naphthalic anhydride by acylation reaction and Suzuki coupling reaction and used for the detection of ClO-. Thiomethyl serves as the recognition group for probe NA, while naphthalimide serves as fluorescent chromophore. The probe exhibited an extremely pronounced blue shift from yellow to blue fluorescence within 1 min after the addition of hypochlorite (ClO-). The probe demonstrates high sensitivity to ClO- with a limit of detection (LOD) of 1.22 µM. Also, probe NA demonstrates excellent selectivity and immunity to interference. Additionally, simple fluorescent test strips containing probe NA were prepared in this study, enabling rapid detection of ClO- in water samples. And NA had been effectively used to image endogenous and exogenous ClO-fluorescence in living cells. The results suggest that probe NA has significant potential for portable detection and biological applications.

Synthesis and application of hypochlorite ratiometric fluorescence probe based on cellulose.

Cellulose is the most abundant natural polymer with good biocompatibility and easy modification characteristics. In this paper, a novel cellulose fluorescence probe CNS for detecting ClO- was prepared by modifying microcrystalline cellulose (MCC). The fluorescence detection results indicate that CNS exhibits a highly specific "ratiometric" and "colorimetric" fluorescence response to ClO-. In the presence of ClO-, the fluorescence color changes from green to cyan. In addition, the color of the solution changes from yellow to colorless, which can be observed with the "naked eye". Considering the good selectivity and anti-interference ability of CNS, the probe can be used for the detection of ClO- in real water samples. Importantly, CNS composite films and test papers were prepared and showed practicability in the detection of ClO-, highlighting its broad application potentials.

Regioselective intramolecular cyclization of o-alkynyl arylamines with the in situ formation of ArXCl to construct poly-functionalized 3-selenylindoles.

In this article, a practical and metal-free method for the synthesis of poly-functionalized 3-selenyl/sulfenyl/telluriumindoles from o-alkynyl arylamines has been achieved. In this protocol, the in situ formation of selenenyl chloride, sulfenyl chloride or tellurenyl chloride is considered as the key intermediate and the 3-selenyl/sulfenyl/telluriumindoles can be obtained in good to excellent yields. Furthermore, the product 2-phenyl-3-(phenylselanyl)-1-tosyl-1H-indole can be selectively oxidized to compounds 2-phenyl-3-(phenylseleninyl)-1-tosyl-1H-indole and 2-phenyl-3-(phenylselenonyl)-1-tosyl-1H-indole in good yields.

Boiling water resistant fully bio-based adhesive made from maleated chitosan and glucose with excellent performance.

Biomass resources are widely considered potential alternatives to formaldehyde-based wood adhesives because of their abundance. In this study, an environmentally friendly biomass adhesive, carboxylated chitosan-glucose (CSC-G), was prepared using chitosan, maleic anhydride, and glucose. The structure and water resistance of the adhesive were analyzed in detail. Maleic anhydride act as a bridge connecting chitosan and glucose, giving the adhesive good water solubility and resistance. The improved water resistance of the CSC-G adhesive was attributed to the formation of covalent cross-linked structures and an increased degree of system cross-linking. Additionally, the curing temperature of the CSC-G adhesive was superior to those of previously reported polyester adhesives. This study not only expands the application scope of fishery waste, but also demonstrates its great potential for the preparation of high-performance plywood.

Synthesis of biomass hyperbranched polyamide resin from cellulose and citric acid for wood adhesive.

Traditional wood adhesives have the problems of excessive dependence on fossil resources and environmental pollution. Cellulose, a renewable biomass resource with a low price and huge output, provides a basis for preparing biomass wood adhesives. In this study, a new type of polyamide resin was prepared by modifying microcrystalline cellulose and reacting with natural citric acid. Specifically, toluenesulfonyl cellulose (TS) was synthesized, and functional amino cellulose (AC) was prepared by a nucleophilic substitution reaction with hyperbranched polyamide (HP). Then cellulose-based hyperbranched polyamide resin (CHP) was prepared by polycondensation with citric acid. The structure of CHP resin was investigated by FTIR, XPS, 13C NMR and GPC, and plywood was prepared to study its mechanical properties. Due to the formation of hyperbranched cross-linked network structure inside the resin, the prepared plywood has excellent properties. The dry shear strength reaches 2.24 MPa, and the strength reaches 1.25 and 1.31 MPa after soaking in water at 63 °C and 93 °C for 3 h. The resin in this study has a simple preparation process and excellent performance, which provides a solid foundation for developing high-performance cellulose-based wood adhesives.

Synthesis of corn bract cellulose-based Au3+ fluorescent probe and its application in composite membranes.

To achieve real-time monitoring of Au3+, a corn bract cellulose-based fluorescent probe MAC-1 for was synthesized. MAC-1 showed good fluorescence properties in DMF-H2O (1:9, v/v, pH = 7.4) solution, showed a fluorescence emission peak at 520 nm with quenching fluorescence properties for Au3+. The structure of MAC-1 was analyzed by SEM (Sample microstructure images), XRD (X-ray diffraction), FTIR (Fourier transform infrared spectroscopy), 1H NMR, Elemental analysis, EDS, Mapping and TG (Thermogravimetry) were analyzed. The fluorescence properties of the probe were also characterized by UV spectrophotometer and fluorescence spectrophotometer. The results showed that the recognition of Au3+ by the probe MAC-1 exhibited high selectivity and high sensitivity. Moreover, it is highly resistant to interference and has a short response time, which can be rapidly responded within 1 min. In addition, to improve the practical application of the probe, the probe was prepared as a fluorescent composite film and the fluorescence effect shown by the fluorescent composite film is consistent with the fluorescence change of the probe MAC-1 itself. The fluorescent composite film also has excellent selectivity and good overall physical and mechanical properties. This study provides a meaningful reference for the detection of Au3+ and further expands the application field of agroforestry waste.