2,7-dicyanocarbazole | 186192-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,7-dicyanocarbazole
• 英文别名: 9H-carbazole-2,7-dicarbonitrile
• CAS: 186192-99-4
• 化学式: C₁₄H₇N₃
• 分子量: 217.23
• InChiKey: AKJRDQOQHIMVTE-UHFFFAOYSA-N

物化性质

• 沸点：
  516.4±30.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,7-dicyanocarbazole 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 2,7-bis(2-imidazolinyl)-9-methylcarbazole dihydrochloride
  参考文献：
  名称：

  Anti-Pneumocystis carinii pneumonia activity of dicationic carbazoles

  摘要：

  A series of 2,7- and 3,6-bis cationic carbazoles was synthesized and evaluated for activity against a rat model of Pneumocystis carinii pneumonia (PCP). The compounds were also tested for inhibition of topoisomerase II and binding to DNA. Several of the compounds proved to be more potent and less toxic than a standard anti-PCP drug (pentamidine). While no quantitative correlation was seen between anti-PCP activity, topoisomerase inhibition and DNA binding, a minimal level of DNA binding was found to be necessary for antimicrobial activity.

  DOI：

  10.1016/s0223-5234(99)80064-6
• 作为产物：
  描述：

  4,4'-二溴-2,2'-二硝基联苯 在 tin(ll) chloride 作用下， 以 乙醇 、 磷酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 2,7-dicyanocarbazole
  参考文献：
  名称：

  Anti-Pneumocystis carinii pneumonia activity of dicationic carbazoles

  摘要：

  A series of 2,7- and 3,6-bis cationic carbazoles was synthesized and evaluated for activity against a rat model of Pneumocystis carinii pneumonia (PCP). The compounds were also tested for inhibition of topoisomerase II and binding to DNA. Several of the compounds proved to be more potent and less toxic than a standard anti-PCP drug (pentamidine). While no quantitative correlation was seen between anti-PCP activity, topoisomerase inhibition and DNA binding, a minimal level of DNA binding was found to be necessary for antimicrobial activity.

  DOI：

  10.1016/s0223-5234(99)80064-6

文献信息

• Comparative Efficacy Evaluation of Dicationic Carbazole Compounds, Nitazoxanide, and Paromomycin against <i>Cryptosporidium parvum</i> Infections in a Neonatal Mouse Model
  作者：Byron L. Blagburn、Kathryn L. Drain、Tracey M. Land、Rachel G. Kinard、P. Hutton Moore、David S. Lindsay、Donald A. Patrick、David W. Boykin、Richard R. Tidwell

  DOI：10.1128/aac.42.11.2877

  日期：1998.11

  The efficacies of dicationic carbazole compounds, nitazoxanide (NTZ), and paromomycin were evaluated against the AUCp1 isolate of Cryptosporidium parvum by using a neonatal mouse model. Compounds were solubilized or suspended in deionized water and administered orally by gavage to neonatal mice at a constant dose rate on days 0 to 5 (treatment started on day 0). Dose rates varied for individual carbazole compounds but ranged from 0.65 to 20 mg/kg of body weight. NTZ was tested at 100 and 150 mg/kg, and paromomycin was tested at 50 mg/kg. Efficacies were determined by comparing numbers of oocysts present in treated versus control mice at necropsy examination on day 6. Demonstrable efficacy was observed for several carbazole compounds, based on significant reductions in the numbers of oocysts recovered from treated mice versus control mice. Compounds 1, 7, and 10 (19.0 mg/kg) reduced oocyst passage in treated mice to less than 5% of that in control mice. Treatment with compounds 6, 8, and 9 (17.0 mg/kg) resulted in reductions of oocyst output to less than 10% of that in controls. Although they were not comparable in efficacy to compounds 1, 6, 7, 8, 9, and 10, treatment with other carbazole compounds resulted in statistically significant reductions in oocyst output in treated versus control mice. Compound 1 retained efficacy resulted in reduction of oocyst output to approximately 6% of that in controls when the dose was reduced to 5 mg/kg. Further reductions in the dose rate resulted in considerable reductions in anticryposporidial activity. Likewise, the efficacies of compounds 9 and 10 were reduced substantially when the doses were lowered to one-half the screening dose. Paromomycin yielded excellent activity (reduction of oocyst output to <2% of that in controls) at a dose of 50 mg/kg. NTZ yielded moderate efficacy as powder and injectable formulations administered at 100 mg/kg orally (reduction of oocyst output to 42 and 26% of that in controls, respectively). Oral administration of the injectable formulation of NTZ at a dose of 150 mg/kg resulted in improved efficacy (oocyst output, <5% of that in controls).

  摘要 对二阳离子咔唑化合物、硝唑胺（NTZ）和帕罗霉素在新生小鼠模型中对AUCp1分离的隐孢子虫（Cryptosporidium parvum）的疗效进行了评估。化合物被溶解或悬浮在去离子水中，并在0至5天（治疗始于第0天）以恒定剂量经口灌胃给新生小鼠。个别咔唑化合物的剂量率有所不同，但范围从0.65到20毫克/千克体重。NTZ以100和150毫克/千克进行测试，帕罗霉素以50毫克/千克进行测试。通过比较尸检检查时治疗组与对照组小鼠中存在的孢子囊数量，确定了疗效。对于几种咔唑化合物，观察到了明显的疗效，基于治疗小鼠中从孢子囊中恢复的数量与对照小鼠的显著减少。化合物1、7和10（19.0毫克/千克）使治疗小鼠中的孢子囊排出量降低到对照小鼠的不到5%。化合物6、8和9（17.0毫克/千克）的治疗导致孢子囊产量降低到对照组的不到10%。尽管它们在疗效上与化合物1、6、7、8、9和10不可比拟，但使用其他咔唑化合物进行治疗导致治疗组与对照组小鼠中的孢子囊产量显著降低。当剂量降低到5毫克/千克时，化合物1保持了疗效，导致孢子囊排出量降低到对照组的约6%。剂量率进一步降低导致抗隐孢子虫活性显著降低。同样，当剂量降低到筛选剂量的一半时，化合物9和10的疗效显著降低。帕罗霉素在50毫克/千克的剂量下表现出优异的活性（孢子囊排出量降低到对照组的<2%）。NTZ作为粉剂和注射剂口服时，以100毫克/千克的剂量表现出中等的疗效（孢子囊排出量分别降低到对照组的42%和26%）。口服150毫克/千克的NTZ注射剂剂型导致改善的疗效（孢子囊排出量<5%）。
• OLEDs based on the emission of interface and bulk exciplexes formed by cyano-substituted carbazole derivative
  作者：Eigirdas Skuodis、Ausra Tomkeviciene、Renji Reghu、Laura Peciulyte、Khrystyna Ivaniuk、Dmytro Volyniuk、Oleksandr Bezvikonnyi、Gintautas Bagdziunas、Dalius Gudeika、Juozas V. Grazulevicius

  DOI：10.1016/j.dyepig.2017.01.016

  日期：2017.4

  photoluminescence quantum efficiency of 43.8% and orange interface exciplex emission with the efficiency of 3.84%. The fluorescent non-doped blue OLED exhibited maximum luminance of 2515 cd/m2 and external quantum efficiency reaching of 2%, while the yellow exciplex OLED exploiting the effect of thermally activated delayed fluorescence had maximum luminance of 6260 cd/m2 and external quantum efficiency of 5.8%

  合成了在取代基中具有氰基的四种咔唑-9-基和二苯基氨基取代的9-乙基咔唑衍生物，并通过实验和理论工具对其进行了表征。研究了热，光学，光物理和电化学性质。所述衍生物表现出适度的热稳定性，超过300℃的5％失重温度。发现所有衍生物都能够在77至111℃的玻璃化转变温度下形成玻璃。固体样品的光学带隙为2.84–3.38 eV。一种衍生物用于制备蓝色非掺杂发射层，并用作激基复合物形成材料，用于制造蓝色和黄色有机发光二极管，其CIE颜色坐标分别为（0.17，0.28）和（0.40，0.52） 。基于黄色激基复合物的器件的电致发光是由于天蓝色体发射与光致发光量子效率为43.8％的橙色界面激基复合物发射的重叠率为3.84％。荧光非掺杂蓝色OLED的最大亮度为2515 cd / m2和外部量子效率达到2％，而利用热活化延迟荧光效应的黄色激基复合物OLED的最大亮度为6260 cd / m 2，外部量子效率为5
• Benzimidazolo[1,2-A]benzimidazole carrying aryl- or arylnitril groups for organic light emitting diodes
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：US10689385B2

  公开（公告）日：2020-06-23

  Novel benzimidazolo[1,2-a]benzimidazoles carrying aryl- or heteroarylnitril groups, an electronic device, comprising said novel benzimidazolo[1,2-a]benzimidazoles carrying aryl- or heteroarylnitril groups, which is preferably an electroluminescent device, a charge transport layer, a charge/exciton blocker layer, or an emitting layer comprising said novel benzimidazolo[1,2-a]benzimidazoles carrying aryl- or heteroarylnitril groups, an apparatus selected from the group consisting of stationary visual display units; mobile visual display units; illumination units; key-boards; items of clothing; furniture; wallpaper, comprising said organic electronic device, or said charge transport layer, said charge/exciton blocker layer, or said emitting layer.

  携带芳基或杂芳基氮基团的新型苯并咪唑并[1,2-a]苯并咪唑，包括所述携带芳基或杂芳基氮基团的新型苯并咪唑并[1,2-a]苯并咪唑的电子装置，最好是电致发光装置、电荷传输层、电荷/激子阻挡层或发光层，其中包含上述携带芳基或杂芳基氮基团的新型苯并咪唑并[1,2-a]苯并咪唑； 选自固定视觉显示装置组的装置；移动视觉显示装置；照明装置；键盘；服装；家具；壁纸，包括所述有机电子装置，或所述电荷传输层、电荷/激子阻挡层或所述发射层。
• Synthesis and characterization of poly(N-alkyloxyarylcarbazolyl-2,7-vinylene) derivatives and their applications in bulk-heterojunction solar cells
  作者：Myungkwan Song、Jin Su Park、Kyung Jin Yoon、Chul-Hyun Kim、Min Joung Im、Jang Soo Kim、Yeong-Soon Gal、Jae Wook Lee、Jun Hee Lee、Sung-Ho Jin

  DOI：10.1016/j.orgel.2010.03.024

  日期：2010.6

  The novel pi-conjugated polymers, poly(N-(3,4-bis(decyloxy) phenyl) carbazolyl-2,7-vinylene) (PCzV) and poly[N-(3,4-bis(decyloxy) phenyl) carbazolyl-2,7-vinylene)-co-2-methoxy- 5-(2-ethylhexyloxy)-1,4-phenylenevinylene}] (PCzV-co-MEH-PPV) were synthesized by using the Gilch polymerization method and their photovoltaic properties were investigated. The newly designed and highly branched polymers, formed from PCzV and PCzV-co-MEH-PPV, are soluble in common organic solvents and easily spin-coated onto indium-tin oxide (ITO) coated glass substrates.The weight-average molecular weights (M(w)) and the polydispersity of the polymers were determined to be in the ranges of 3.86-7.9 x 10(4) and 1.60-2.05, respectively. Bulk-heterojunction solar cells, with ITO/PEDOT: PSS/polymer: PC(61)BM/TiO(x)/Al configurations, were fabricated. The solar cell based on PCzV-co-MEH-PPV: PC(61)BM (1:6 wt/wt) displays a higher photovoltaic performance as compared to that produced from PCzV: PC61BM (1: 6 wt/wt). The bulk-heterojunction solar cell with PCzV-co-MEH-PPV: PC61BM (1: 6 wt/wt) has a power conversion efficiency (PCE) of 2.31% (J(sc) = 6.43 mA/cm(2), V(oc) = 0.82 V, FF = 44%), measured using an AM 1.5 G solar simulator at 100 mW/cm(2) light illumination. (C) 2010 Elsevier B. V. All rights reserved.
• CARBAZOLES FOR TREATING MICROBIAL INFECTIONS
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP0831811B1

  公开（公告）日：2003-11-19