3,8-dibromobenzo[c]cinnoline | 79580-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,8-dibromobenzo[c]cinnoline
• CAS: 79580-35-1
• 化学式: C₁₂H₆Br₂N₂
• 分子量: 338.001
• InChiKey: DHEJMXHUNWPNME-UHFFFAOYSA-N

物化性质

• 熔点：
  237 °C
• 沸点：
  274.2±23.0 °C(Predicted)
• 密度：
  1.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,8-dibromobenzo[c]cinnoline 在 水 、 palladium diacetate 、 sodium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基乙酰胺 、 二乙二醇 为溶剂， 反应 20.0h， 生成 benzo[c]cinnoline-3,8-dicarboxylic acid
  参考文献：
  名称：

  Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties

  摘要：

  A four-step route was designed to synthesize 3,8-benzo[c]cinnoline dicarboxylic acid (4). New conjugated polymers, POXD (I) and POXD (T), containing benzo[c]cinnoline and oxadiazole moieties, were obtained by thermal cyclodehydration of their soluble polyhydrazide precursors PHA (I) and PHA (T), respectively. Two reduction peaks were observed for these new conjugated polymers during CV cathodic scan. From the CV voltammograms combined with the results from molecular simulation, we concluded that the first reduction occurred at oxadiazole moiety and benzo[c]cinnoline moiety was responsible for the second reduction. It indicates that oxadiazole has stronger electron affinity than benzo[c]cinnoline. We proposed a mechanism to explain this two-stage reduction process. Due to the planar and electron-accepting ability of benzo[c]cinnoline and oxadiazole moieties, POXD (I) and POXD (T) exhibited very low LUMO (-3.42 and -3.45 eV) and HOMO (-6.23 and -6.27 eV) energy levels. They can be used as hole-blocking or electron-injection layers for OLED applications. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.10.059
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 copper(l) iodide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.5h， 生成 3,8-dibromobenzo[c]cinnoline
  参考文献：
  名称：

  一种以苯并[c]噌啉为受体的化合物及其应用

  摘要：

  本发明公开了一种以苯并[c]噌啉为受体的化合物，属于有机电致发光功能材料及器件技术领域。该化合物的结构通式如式(Ⅰ)所示，式(Ⅰ)中，D1、D2相同均选自取代或未取代的咔唑基、吩唖嗪基、吩嗪基、吩噁嗪基、吩噻嗪基或吖啶基的给电子基团。本发明还提供了一种以苯并[c]噌啉为受体的化合物在有机电致发光器件中的应用以及有机电致发光器件。本发明提供的以苯并[c]噌啉为受体的化合物通过特定位置引入特定的给电子基团修饰构成的全新化合物具有较好的能量传输能力和电荷传输能力，可显著提高发光器件的发光稳定性，可广泛应用在OLED发光器件及显示装置上作为发光层主体材料、或者热活性延迟荧光(TADF)发光材料使用。结构通式如式(I)所示：。

  公开号：

  CN111574505B

文献信息

• Aryl and heteroaryl compounds as antibacterial and antifungal agents
  申请人：——

  公开号：US20030220340A1

  公开（公告）日：2003-11-27

  This invention provides novel compounds possessing antibacterial and/or antifungal and/or antitumor activity. Pharmaceutical compositions containing these compounds, methods of making and methods for using these compounds are also provided.

  这项发明提供了具有抗菌和/或抗真菌和/或抗肿瘤活性的新化合物。还提供了含有这些化合物的药物组合物、制备这些化合物的方法以及使用这些化合物的方法。
• Synthesis and properties of air-stable n-channel semiconductors based on MEH-PPV derivatives containing benzo[c]cinnoline moieties
  作者：Jyh-Chien Chen、Hsin-Chung Wu、Chi-Jui Chiang、Tuo Chen、Li Xing

  DOI：10.1039/c3tc32505a

  日期：——

  In this study we synthesized three novel poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] (MEH-PPV) derivatives that differ in terms of their ratios of heterocyclic benzo[c]cinnoline moieties: P50 containing only MEH-PPV/benzo[c]cinnolinevinylene (BZCV) alternating segments and P25 and P10 containing both MEH-PPV/BZCV alternating segments and MEH-PPV block segments. UV-Vis and PL spectra of

  在这项研究中，我们合成了三种新颖的聚[2-甲氧基-5-（2-乙基己基氧基）-1,4-亚苯基亚乙烯基]（MEH-PPV）衍生物，它们的杂环苯并[ c ] cinnoline部分的比例不同：P50仅包含MEH-PPV /苯并[ c ]肉桂基亚乙烯基（BZCV）交替链段，P25和P10包含MEH-PPV / BZCV交替链段和MEH-PPV嵌段链段。UV-Vis和这些聚合物的PL光谱显示的值λ UV最大值和λ PL最大的是范围从440到489和从492到551分别纳米，; 当加入其他苯并[ c]时，这些波长会蓝移] cinnoline部分。我们还观察到了从MEH-PPV / BZCV交替段到MEH-PPV嵌段段的能量转移。P50在其主链中具有交替结构，显示出溶剂变色效应，在非极性溶剂中发出绿光，在极性溶剂中发出黄光。使用循环伏安法测量的这些聚合物的HOMO和LUMO能级分别为-5.11至-5.62和-3
• Synthesis and characterization of heterocyclic conjugated polymers containing planar benzo[c]cinnoline and tetraazapyrene structures for organic field-effect transistor application
  作者：Shih-Wei Lee、Shih-Hsuan Chien、Jyh-Chien Chen、Shih-Hao Wang、Lee-Yih Wang、Bo-Han Lai、Chien-Lung Wang

  DOI：10.1016/j.orgel.2018.12.027

  日期：2019.3

  522 and 534 nm, respectively. From cyclic voltammertry measurement, TAPTVT and BZCTVT exhibited low LUMO (−3.61 and −3.47 eV) and HOMO (−5.64 and −5.63 eV) energy levels. Even though BZC and TAP were planar structures, BZCTVT and TAPTVT showed large dihedral angles between alkylated thiophene and TVT (10.8–22.6°), and between alkylated thiophene and BZC and TAP (22.2–30.3°) based on their simulated energy-minimized

  通过在微波反应器中使用Stille偶联聚合反应，分别制备了含苯并[ c ] cinnoline（BZC）和四氮杂ap烯（TAP）的杂环共轭聚合物BZCTVT和TAPTVT。BZC和TAP充当受体，噻吩-亚乙烯基-噻吩（TVT）充当供体。烷基化噻吩是受体和供体之间的连接基。这是第一次将四氮杂yr烯掺入到共轭聚合物中。BZCTVT和TAPTVT的膜分别在522和534 nm处显示最大吸收波长。根据循环伏安法测量，TAPTVT和BZCTVT表现出较低的LUMO（−3.61和−3.47 eV）和HOMO（−5.64和−5.63 eV）能级。尽管BZC和TAP是平面结构，但是BZCTVT和TAPTVT根据模拟的能量最小化几何结构显示出烷基化噻吩和TVT之间的大二面角（10.8–22.6°），以及烷基化噻吩与BZC和TAP之间的大二面角（22.2–30.3°） 。基于TAPTVT和BZCTVT的底栅，
• Anti-Pneumocystis carinii pneumonia activity of dicationic carbazoles
  作者：DA Patrick、DW Boykin、WD Wilson、FA Tanious、J Spychala、BC Bender、JE Hall、CC Dykstra、KA Ohemeng、RR Tidwell

  DOI：10.1016/s0223-5234(99)80064-6

  日期：1997.10

  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.
• UV-Irradiation-Enhanced Photoluminescence Emission of Polyfluorenes Containing Heterocyclic Benzo[<i>c</i>]cinnoline Moieties
  作者：Hsin-Chung Wu、Jyh-Chien Chen、Hong-Ze Lin

  DOI：10.1021/acs.macromol.5b01108

  日期：2015.7.14

  Polyfluorenes (PFO) derivatives, containing different ratios of heterocyclic, electron-withdrawing benzo[c]cinnoline moieties, BF10, BF25, and BF50 were synthesized by Suzuki coupling reaction. Photoluminescence (PL) spectra showed red-shifted emission peaks at around 500 nm for dilute polymer solutions and at around 530 nm for film samples. The PL quantum yields of polymer dilute solutions decreased as the ratios of benzo [c] cinnoline moieties in main chain increased. By UV irradiation (352 nm), the PL intensity of dilute polymer solutions was enhanced. The PL emission enhancement was attributed to the shorter conjugated length and the reduced donor acceptor interaction caused by oxygen-containing groups that were formed on fluorene moieties by UV irradiation. The enhanced emission could be quenched further by the addition of proton donors such as trifluoroacetic acid. The completely alternating polymer BF50 consisting of fluorene and benzo[c]cinnoline moieties in dilute THF solution showed a linear relationship between UV doses and PL quantum yields after UV irradiation. It exhibited good potential for UV-sensing applications.