2,5-pyridinedicarboxylic dihydrazide | 6011-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,5-pyridinedicarboxylic dihydrazide
• 英文别名: pyridine-2,5-dicarbohydrazide；pyridine-2,5-dicarboxylic acid dihydrazide；Pyridin-2,5-dicarbonsaeure-dihydrazid；Isocinchomeronsaeure-dihydrazid
• CAS: 6011-55-8
• 化学式: C₇H₉N₅O₂
• mdl: MFCD05863351
• 分子量: 195.181
• InChiKey: OTPQUWGVUDNOLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-pyridinedicarboxylic dihydrazide 在 氢氧化钾 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2,5-bis<5'-(2''-dimethylaminoethylthio)-1',3',4'-thiadiazol-2'-yl>pyridine
  参考文献：
  名称：

  Barlin, Gordon B., Australian Journal of Chemistry, 1985, vol. 38, # 10, p. 1491 - 1497

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-吡啶二甲酸二乙酯 在 乙醇 、 一水合肼 作用下， 生成 2,5-pyridinedicarboxylic dihydrazide
  参考文献：
  名称：

  Shinohara et al., Kobunshi Kagaku, 1958, vol. 15, p. 839,844

  摘要：

  DOI：

文献信息

• New electroluminescent bipolar compounds for balanced charge-transport and tuneable colour in organic light emitting diodes: triphenylamine–oxadiazole–fluorene triad molecules
  作者：Kiran T. Kamtekar、Changsheng Wang、Sylvia Bettington、Andrei S. Batsanov、Igor F. Perepichka、Martin R. Bryce、Jin H. Ahn、Mohammad Rabinal、Michael C. Petty

  DOI：10.1039/b604543j

  日期：——

  This work describes bipolar 2,5-diaryl-1,3,4-oxadiazole–fluorene hybrids which incorporate triphenylamine or carbazole units within the π-electron system, viz. compounds 7, 8, 14 and 16. A related bipolar bis(oxadiazolyl)pyridine system 20 is reported. The syntheses of these five new materials are discussed, along with their optoelectronic absorption and emission properties, and their solution electrochemical redox properties. Anodic electropolymerisation of 20 was observed. Calculations using DFT (density functional theory) establish that they all possess a significantly higher HOMO energy level (by 0.60–1.02 eV) than 1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazol-5-yl]benzene (OXD-7) due to the presence of electron-rich amine moieties and increased conjugation lengths, thereby leading to more balanced charge-transport characteristics. Devices were fabricated by spin-coating techniques using the bipolar compounds as the emitters in the simple device architecture ITO:PEDOT-PSS:X:Ca/Al (X = 7, 8, 14, 16 or 20). The turn-on voltages were 2.9, 5.5, 3.6, 4.5 and 3.4 V for the devices incorporating 7, 8, 14, 16 and 20, respectively. The highest external quantum efficiency (EQE) was observed for compound 7: viz. EQE 0.36%; current efficiency 1.00 cd A−1; power efficiency 0.56 lm W−1 at 5.7 V. The EQE of the device fabricated from 8 was considerably lower than for devices using other materials due to low light emission. The EL emission peaked at λmax 430, 487, 487 and 521 nm for 8, 14 and 16, and 7, respectively. For the 20 device λmax = 521 nm and 564 nm. Thus the HOMO–LUMO gap has been modified, allowing the colour of the emitted light to vary from light blue through to green by the systematic chemical modification of the molecular subunits. The high chemical and thermal durability of these materials combined with the simplicity of the device structure and low turn-on voltages offers considerable potential for OLED applications.

  本工作描述了包含三苯胺或咔唑单元的双极性2,5-二芳基-1,3,4-噁二唑-荧光烯杂化物，即化合物7、8、14和16。还报道了一种相关的双极性双(噁二唑基)吡啶系统20。讨论了这五种新材料的合成，以及它们的光电吸收和发射特性及其溶液电化学氧还原特性。观察到20的阳极电化学聚合。使用密度泛函理论（DFT）计算表明，它们的HOMO能级明显高于1,3-双[2-(4-叔丁基苯基)-1,3,4-噁二唑-5-基]苯（OXD-7），提高了0.60–1.02 eV，这得益于富电子的胺基团和增加的共轭链长，从而导致更均衡的电荷传输特性。通过旋涂技术制造了器件，将这些双极性化合物作为发射体用于简单的器件结构ITO:PEDOT-PSS:X:Ca/Al（X = 7、8、14、16或20）。融入7、8、14、16和20的器件的开启电压分别为2.9、5.5、3.6、4.5和3.4 V。化合物7的外量子效率（EQE）最高：即EQE 0.36%；电流效率1.00 cd A⁻¹；在5.7 V时，功率效率为0.56 lm W⁻¹。由8制成的器件的EQE明显低于使用其他材料的器件，原因是发光较弱。EL发射在8、14、16和7时分别达到峰值λmax 430、487、487和521 nm。对于20器件，λmax = 521 nm和564 nm。因此，HOMO–LUMO间隙得到了调节，使得发出光的颜色可以通过分子亚单位的系统化化学修饰从浅蓝色变化到绿色。这些材料的高化学和热稳定性，加上器件结构的简易性和低开启电压，为OLED应用提供了可观的潜力。
• Efficient synthesis of Some Novel Symmetrical and Unsymmetrical Pyridine bis-1,2,4-triazoles and bis-1,3,4-thiadiazoles
  作者：Naser Foroughifar、Akbar Mobinikhaledi、Abdolhossein Rafiee

  DOI：10.3184/174751914x13896291543361

  日期：2014.2

  series of novel bis-1,2,4-triazoles and bis-1,3,4-thiadiazoles bearing pyridine rings was synthesised, by multistep reaction sequences, in good to high yields. Reaction of pyridine-2,5-bis- and pyridine-2,6-bis-carbohydrazides with alkyl- or aryl-isothiocyanates gave the corresponding bis(thiosemicarbazide) derivatives, which could be cyclised under strongly basic conditions to give novel pyridine bis(1

  通过多步反应顺序合成了一系列新型双-1,2,4-三唑和双-1,3,4-噻二唑类吡啶环，产率高。吡啶-2,5-双-和吡啶-2,6-双-碳酰肼与烷基-或芳基-异硫氰酸酯反应得到相应的双（氨基硫脲）衍生物，可以在强碱性条件下环化得到新型吡啶双（ 1,2,4-三唑-3-硫醇）。然而，在强酸性条件下获得了相应的双（2-氨基-1,3,4-噻二唑）。报道了新化合物的合成路线和光谱表征。
• Intramolecular charge transfer induced by deprotonation of hydroxyl groups in π-conjugated polymers with π-deficient aromatic rings
  作者：Isao Yamaguchi、Hidehito Mitsuno

  DOI：10.1016/j.reactfunctpolym.2010.11.014

  日期：2011.2

  compounds suggests the expansion of the π-conjugation system along the polymer chain. The reaction of polymer-4 and model-2 with NaH caused the dehydration of the OH groups, which induced an intramolecular charge transfer (ICT) from the ONa group to the Tz ring. The ICT affected the optical properties of the polymers and the model compounds. The cast films of polymers obtained in this study underwent electrochemical

  由对苯撑（Ph）和1,3,4-恶二唑（Oz）或4-辛基苯基-1,3,4-三唑（OctOz）环组成的π共轭聚合物[聚合物-1：（Ph-Oz）n和聚合物2：（Ph-OctTz）n ]以及由9,9-二己基-2,7-芴（Flu）和Oz或1-（4-羟苯基）-1,3,4-三唑（HOPhTz）组成的聚合物）通过聚合合成[聚合物3：（Ph-Oz-Py-Oz-Flu）n和聚合物4：（Ph-HOPhTz-Py-HOPhTz-Flu）n（Py = 2,5-吡啶）]的环。分别由多磷酸和Pd配合物催化。模型化合物（模型1：Ph-Oz-Py-Oz-Ph，模型2合成了Ph-HOPhTz-Py-HOPhTz-Ph和模型3：Ph-OctPhTz-Py-OctPhTz-Ph）。该事实λ最大的聚合物的波长均比模型化合物的更长表明沿着聚合物链的π共轭系统的扩展。的反应聚合物-4和模型-2用NaH引起OH基团的脱水，从而诱发从ON
• Meyer,H.; Staffen, Monatshefte fur Chemie, 1913, vol. 34, p. 521
  作者：Meyer,H.、Staffen

  DOI：——

  日期：——
• Supaniewski et al., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1955, vol. 3, p. 55,58
  作者：Supaniewski et al.

  DOI：——

  日期：——