Hit to Leads with Cytotoxic Effect in Leukemic Cells: Total Synthesis Intermediates as a Molecule Treasure Chest

A previously designed and developed 12-step total synthesis that includes [1,1′-biphenyl]-2-amine and carbazole intermediates and that ultimately produces the carbazole alkaloid carbazomycin G was exploited as a screening compound library with the goal of identifying potential lead compound(s) with cytotoxic effect. These compounds were investigated by using in-vitro tests involving the two human cell lines HL-60 and MOLM-13, which both model acute myeloid leukaemia (AML). The in-vitro biological test results were used together with the molecular structures of the various intermediates in a concise SAR analysis. Several of the intermediates revealed cytotoxicity (IC₅₀<10⁻⁴ M), although the final natural product carbazomycin G did not reveal cytotoxicity versus the two said human cell lines.     

Electroactive polymers containing 3-arylcarbazolyl units as hole transporting materials for OLEDs

Monomers and their polymers containing 3-arylcarbazolyl electrophores have been synthesized by the multi-step synthetic route. The materials were characterized by thermo-gravimetric analysis, differential scanning calorimetry and electron photoemission technique. The polymers represent materials of high thermal stability having initial thermal degradation temperatures in the range of 331–411 °C. The glass transition temperatures of the amorphous polymeric materials were in the rage of 148–175 °C. The electron photoemission spectra of thin layers of monomers showed ionization potentials in the range of 5.6–5.65 eV. Hole-transporting properties of the polymers were tested in the structures of organic light emitting diodes with Alq₃ as the green emitter. The device containing hole-transporting layers of polyether with 3-naphthylcarbazolyl groups exhibited the best overall performance with a maximum current efficiency of 3.3 cd/A and maximum brightness of about 1000 cd/m².     

Optimization of solvent crystallization process in obtaining high purity anthracene and carbazole from crude anthracene

Solvent crystallization is the main method used for preparing anthracene and carbazole from the crude anthracene. The key to the optimization of this method is improving the solubility selectivity of the solvent by means of solvent modulating and process optimization. In this study, the solubility of anthracene, phenanthrene, and carbazole in xylene, dimethylformamide (DMF), DMF with amine/amide, isopropanolamine, and chlorobenzene is examined and the solid‐liquid ternary anthracene–carbazole–DMF/(DMF+19.96% isopropanolamine) system phase diagram is determined and applied in the solvent crystallization process. The results showed that the solubility selectivity of xylene increases with increased temperature. Also, selectivity increases with an increase of the amount of isopropanolamine in the mixture of DMF and isopropanolamine, while decreases with increased temperature. Through multiple washings of crude anthracene with xylene, DMF+19.96% isopropanolamine, and chlorobenzene, it was possible to obtain anthracene and carbazole of purity higher than 98 wt %. © 2013 American Institute of Chemical Engineers AIChE J, 60: 275–281, 2014     

新型近红外咔唑吲哚类硼酸酯荧光探针的合成与表征

以咔唑为起始原料,经过与亲电取代反应、Vilsmeier反应、溴化反应以及与双联频哪醇硼酸酯的偶联反应,合成了N-乙基咔唑-3-甲醛-6-苯硼酸酯,以合成的N-乙基咔唑-3-甲醛-6-苯硼酸酯,以合成的乙基取代咔唑硼酸,以合成的乙基取代咔唑硼酸酯醛与1,2,3,3-四甲基-3H-吲哚碘化物缩合,合成了一种新型近红外咔唑吲哚啉类硼酸酯荧光探针,其结构经过1H NMR,IR进行了表征。     

3,6-二氨基咔唑衍生物的合成及与DNA的相互作用

以咔唑为起始原料,通过硝化、还原、酰化合成了3,6-二(3-丙酰氯氨基)咔唑,再分别与4个含氮化合物进行烷基化反应,合成了4个具有不同取代基的3,6-二氨基咔唑衍生物,用1HNMR、13CNMR和ESI-MS进行了结构表征。通过UV-Vis谱、荧光光谱、圆二色谱和热变性实验研究了合成化合物与小牛胸腺(Ct)-DNA的结合能力。结果表明,化合物Ⅳa及Ⅳb作为DNA嵌入剂与Ct-DNA有较好的结合能力。     

Carbazole based hole transporting materials for solid state dye sensitizer solar cells: role of the methoxy groups

The synthesis of new organic hole transporting materials (HTMs) based on 3,6‐disubstituted 9H‐carbazole‐3,6‐diamine,N,N,N′,N′‐tetraphenyl‐9‐(4‐methoxyphenyl) derivatives and their applications in solid state dye sensitizer solar cells (DSSCs) are described. The effect of the methoxy group localized on the para position of the diphenylamine moieties on the thermal, electronic and electrochemical properties and photovoltaic performance is discussed. In solid state DSSCs, utilization of the aforementioned HTMs in combination with the dye D102 (TiO₂/D102/HTM/Au) shows a positive influence of the methoxy group on the photovoltaic conversion efficiency compared with unsubstituted diphenylamine grafted groups. A study on the concentration of the HTM is also carried out and shows an optimal concentration around 200 mg mL^?1. Without further optimization, the best device gives a power conversion efficiency of 1.75% under AM 1.5 solar irradiation (100 mW cm^?2).     

咔唑生产技术浅谈

对蒸馏-溶剂法、溶剂-蒸馏法和双溶剂法生产咔唑的3种实用工艺进行了评述。结果表明,双溶剂法工艺的咔唑得率高、劳动强度小、投资少,可以充分利用煤焦油中的咔唑资源。该工艺适用于50万t/a以下的煤焦油加工厂,经济效益好。     

Synthesis of Poly(arylene vinylene)s Containing Carbazole,Triphenylamine, and Phenothiazine Rings in the Backbone by Cascade Suzuki-Heck Reactions

Three new conjugated poly(arylene vinylene) structures containing triphenylamine, carbazole, or phenothiazine as aromatic units in the main chain and connected by vinyl segments have been synthesized by a cascade Suzuki-Heck reactions. The best reaction yields were obtained by coupling of the dibromoarylamines with vinyl segments via Suzuki-Heck reaction cascade using Pd(OAc)₂ as catalyst and triethylamine as solvent. The polymers were obtained as fully or partially soluble materials in chlorinated or aprotic polar solvents. They were characterized by ¹H-NMR, FT-IR, UV-Vis, and photoluminescence spectroscopy. Cyclic voltammetry characteristics were studied in solution and as solid thin films deposited on the electrode surface.     

从煤焦油分离提纯蒽和咔唑工艺改进探讨

溶剂结晶-精馏法是目前从煤焦油中分离提纯蒽和咔唑的比较先进成熟的已工业化工艺,其杂质的脱除主要在溶剂结晶部分,操作步骤多,但杂质分离效果还不是很理想,最终影响产品纯度。通过实验研究,发现结晶物中高杂质母液的滞留是该工艺杂质分离效果难以提高的关键因素。提出了溶剂结晶结合抽滤-精馏法新工艺,给结晶箱组合气液分离器,实现结晶同步抽滤功能,降低结晶物的母液滞留量,可提高分离效果,减少溶剂循环量,提高产品纯度和回收率,降低装置能耗,增加产能,有较好的经济性。     

Synthesis,characterization and corrosion protection properties of poly(N-vinyl carbazole-co-glycidyl methacrylate) coatings on low nickel stainless steel

Methacrylate based copolymers are considered as one of the best organic coating materials for anticorrosive application. Poly(N-vinyl carbazole-co-glycidyl methacrylate) have been synthesized by free radical solution polymerization technique from different mole ratios of N-vinyl carbazole (N-Vc) and glycidyl methacrylate (GMA) and characterized using Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (¹H NMR and ¹³C NMR). Thermal analyses of the poly(N-Vc-co-GMA) were performed by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The number average molecular weight (M_n) of different compositions of the same was determined by gel permeation chromatography (GPC). The corrosion performances of low nickel stainless steel specimens coated with different composition of copolymers were investigated in 1 M H₂SO₄ using potentiodynamic polarization, electrochemical impedance spectroscopic (EIS) method, scanning electron microscopic (SEM) and energy dispersive X-ray analysis (EDAX). Poly(N-Vc-co-GMA) have been provided in order to achieve adherent, low permeability to aggressive ions as well as environmentally favored good anticorrosive coating. Electrochemical corrosion test and surface analysis results clearly showed that poly(N-Vc-co-GMA) coatings served as a stable host matrix on low nickel stainless steel against corrosion. It was also observed that the coatings of poly(N-Vc-co-GMA) with equal mole ratio of N-Vc and GMA exhibited the best corrosion resistance among all combinations.