White and Red Organic Light Emitting Materials

Derivatives of 2,3-(1,4-dialkoxyaceno)norbornadiene underwent ring-opening metathesis polymerization (ROMP) upon the catalysis of a ruthenium complex to afford the corresponding polymers. The polymeric materials containing anthracene chromophores emit white electro-luminescence, which can be fabricated into light-emitting diodes (LED). The broad emission band is composed of a blue emission from anthracene and a red emission from aggregates. A single layer device, ITO/polymer/Ca/Al, can be turned on at 7V and exhibits maximum intensity 427 cd/m2 at 15 V. A double layer device, ITO/polymer/TPBI/Mg:Ag (TPBI = (2,2′,2"-(1,3,5-benzenetriyl)-tris(1-phenyl-1H-benzimidazole)) displayed blue light with turn-on voltage 6 V and maximal intensity 930 cd/m2 at 15 V.Derivatives of bisindolylmaleimide were found to form amorphous solid films which exhibit intensive red luminescence. The property of forming glasses can be ascribed to the nonplanar geometry of these molecules. LED devices were fabricated by a layer of pure dye sandwiched between two charge transporting films. The yellow emission spectrum of the devices utilizing Alq (tris(8-hydoxyquinolinato)aluminum) contains a green component from Alq. Pure red emissions can be achieved by replacing Alq with TPBI. Typical devices can be turned on at ～3 V with maximal intensity 2000 cd/m2. White color devices are under current investigation, in which the green Alq layer is replaced by its blue derivative (bis(2-methyl-8-hydoxyquinolinato)(phenolato)aluminum).     

双吲哚马来酰亚胺硫脲化合物的合成及抗肿瘤活性

基于双吲哚马来酰亚胺化合物和硫脲化合物的结构及多样的生物活性,通过1-氨基-3,4-二(吲哚-3-基)-3-吡咯啉-2,5-二酮与异硫氰酸酯反应,合成了17种新的3,4-二(吲哚-3-基)-2,5-二酮-1-吡咯亚胺硫脲类化合物,化合物的结构通过1H NMR、13C NMR、HRMS等进行了表征。该系列化合物的初步抗肿瘤活性测试表明,它们都对细胞周期分裂蛋白25B(CDC 25B)表现出良好的抑制活性(大部分化合物的抑制率在96%以上),具有潜在的抗肿瘤活性及应用价值。     

N-苯甲酰胺基取代的双吲哚马来酰亚胺类化合物的合成与荧光性质研究

以琥珀酰亚胺为原料,经溴代、吲哚加成、与水合肼反应、酰基化和烷基化等反应,设计合成了6a～6c和7a～7b共5个新型N-苯甲酰胺基取代的双吲哚马来酰亚胺类化合物,其结构经IR,1H NMR和HRMS等进行了表征,并研究了该类化合物的紫外、荧光性能和热性质.研究表明,N-苯甲酰胺基取代的双吲哚马来酰亚胺类化合物的紫外吸收光谱在360～400和450～500 nm显示两个主要吸收峰,将N原子甲基化和苄基化后,紫外吸收峰波长发生红移.以化合物紫外最大吸收波长为激发波长,目标化合物的荧光发射光谱在560～620 nm有最大发射峰,7a有最大的荧光量子产率,7a在不同溶剂中随溶剂极性的增大,量子产率没有明显的变化规律,讨论了化合物的结构对荧光性能的影响.热学性质研究表明,化合物7a和7b的玻璃化转变温度(Tg)分别为116和80℃,目标化合物的分解温度接近400℃.     

Synthesis and Antiplasmodial Activity of Bisindolylcyclobutenediones

Malaria is one of the most dangerous infectious diseases. Because the causative Plasmodium parasites have developed resistances against virtually all established antimalarial drugs, novel antiplasmodial agents are required. In order to target plasmodial kinases, novel N-unsubstituted bisindolylcyclobutenediones were designed as analogs to the kinase inhibitory bisindolylmaleimides. Molecular docking experiments produced favorable poses of the unsubstituted bisindolylcyclobutenedione in the ATP binding pocket of various plasmodial protein kinases. The synthesis of the title compounds was accomplished by sequential Friedel-Crafts acylation procedures. In vitro screening of the new compounds against transgenic NF54-luc P. falciparum parasites revealed a set of derivatives with submicromolar activity, of which some displayed a reasonable selectivity profile against a human cell line. Although the molecular docking studies suggested the plasmodial protein kinase PfGSK-3 as the putative biological target, the title compounds failed to inhibit the isolated enzyme in vitro. As selective submicromolar antiplasmodial agents, the N-unsubstituted bisindolylcyclobutenediones are promising starting structures in the search for antimalarial drugs, albeit for a rational development, the biological target addressed by these compounds has yet to be identified.     

新型双吲哚马来酰亚胺衍生物的合成

以1-(3-氧代四氢吡喃丙基)-吲哚-3-乙醛酸甲酯(5)和吲哚-3-乙酰胺(6)为原料,在催化剂叔丁醇钾的四氢呋喃溶液存在下发生偶合反应,经浓盐酸处理得脱保护的中间体7,再经甲磺酰化反应、氨解反应得到4种新的具有不同氨烷基侧链的双吲哚马来酰亚胺衍生物9a,9b,9d,9e.目标产物结构通过1H NMR,13C NMR,MS和HRMS确证.