2-(4,5-bis(butylthio)-1,3-dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-d]pyridazine-4,7-dione | 1359021-05-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4,5-bis(butylthio)-1,3-dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-d]pyridazine-4,7-dione
• 英文别名: 2-[4,5-Bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5,6-dihydro-[1,3]dithiolo[4,5-d]pyridazine-4,7-dione；2-[4,5-bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5,6-dihydro-[1,3]dithiolo[4,5-d]pyridazine-4,7-dione
• CAS: 1359021-05-8
• 化学式: C₁₆H₂₀N₂O₂S₆
• 分子量: 464.743
• InChiKey: RVQGBOAZKHKZKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  210
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(4,5-bis(butylthio)-1,3-dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-d]pyridazine-4,7-dione 在 三氯氧磷 作用下， 以90%的产率得到2-(4,5-bis(butylthio)-1,3-dithiol-2-ylidene)-4,7-dichloro-[1,3]dithiolo[4,5-d]pyridazine
  参考文献：
  名称：

  合成和基于3,6- diarylpyridazine稠合硫富瓦烯的T形有机缀合物的性质†

  摘要：

  描述了一种容易的合成方法，用于π-膨胀的四硫富瓦烯衍生物。3,6-二氯哒嗪稠合的四硫富富烯的Suzuki反应与苯基硼酸 或者 联苯硼酸给出了一系列新颖的T形有机π共轭物。通过循环伏安法和紫外可见光谱法的结合，对缀合物的电子性质进行了实验研究。它们的HOMO和LUMO能级估计约为-5 eV和-3.2 eV，分别是p沟道和n沟道场效应晶体管中的空气工作稳定性范围。经验证，只有一个带有较长烷基链的共轭物（n = 1，R = n -C 18 H 37）能在介晶相中自组装成层状结构，其薄膜器件的最佳载流子迁移率是4.5 ×10 -5 cm 2 V -1 s -1。

  DOI：

  10.1039/c3ob40704g
• 作为产物：
  描述：

  1,3-二硫杂环戊二烯-2-硫酮-4,5-二甲酸二甲酯 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(4,5-bis(butylthio)-1,3-dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-d]pyridazine-4,7-dione
  参考文献：
  名称：

  The pyridazine–tetrathiafulvalene conjugates: synthesis, photophysical, and electrochemical properties

  摘要：

  To study the electronic interactions in donor acceptor (D A) conjugates as a precursor of optoelectronic materials, a series monopyridazine-annulated tetrathiafulvalenes and a bispyridazine-annulated tetra-thiafluvalene were synthesized by a condensation reaction of 2,3-dimethoxycarbonyl-6,7-dibutylthiotetrathiafulvalene or/and 2,3,6,7-tetramethoxycarbonyltetrathiafulvalene with hydrazine hydrate and structurally characterized by conventional chemical and physical methods. Their electronic properties have been studied experimentally by the combination of electrochemistry and UV-vis spectroscopy. All of monopyridazine-tetrathiafulvalene conjugates 7-13 show intramolecular charge transfer interaction in ground states, which is rationalized on the basis of density functional theory. Their HOMO energy levels and Er values were estimated to be -4.88 to -5.07 eV from cyclic voltammetry and 2.43-2.79 eV from the absorption spectra, respectively. The X-ray crystallographic analyses of the pyridazine tetrathiafulvalene conjugates 7, 11-13 are also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.034

文献信息

• The pyridazine–tetrathiafulvalene conjugates: synthesis, photophysical, and electrochemical properties
  作者：Ningjuan Zheng、Bao Li、Changwei Ma、Tie Chen、Yuhe Kan、Bingzhu Yin

  DOI：10.1016/j.tet.2011.12.034

  日期：2012.2

  To study the electronic interactions in donor acceptor (D A) conjugates as a precursor of optoelectronic materials, a series monopyridazine-annulated tetrathiafulvalenes and a bispyridazine-annulated tetra-thiafluvalene were synthesized by a condensation reaction of 2,3-dimethoxycarbonyl-6,7-dibutylthiotetrathiafulvalene or/and 2,3,6,7-tetramethoxycarbonyltetrathiafulvalene with hydrazine hydrate and structurally characterized by conventional chemical and physical methods. Their electronic properties have been studied experimentally by the combination of electrochemistry and UV-vis spectroscopy. All of monopyridazine-tetrathiafulvalene conjugates 7-13 show intramolecular charge transfer interaction in ground states, which is rationalized on the basis of density functional theory. Their HOMO energy levels and Er values were estimated to be -4.88 to -5.07 eV from cyclic voltammetry and 2.43-2.79 eV from the absorption spectra, respectively. The X-ray crystallographic analyses of the pyridazine tetrathiafulvalene conjugates 7, 11-13 are also reported. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and properties of T-shaped organic conjugates based on 3,6-diarylpyridazine-fused tetrathiafulvalene
  作者：Ningjuan Zheng、Hongda Li、Guangyan Sun、Keli Zhong、Bingzhu Yin

  DOI：10.1039/c3ob40704g

  日期：——

  gave a series of novel T-shaped organic π-conjugates. The electronic properties of the conjugates were studied experimentally by the combination of cyclic voltammetry and UV-vis spectroscopy. Their HOMO and LUMO energy levels are estimated to be about −5 eV and −3.2 eV, which are the air operating stability ranges in the p-channel and n-channel field effect transistors, respectively. Only one conjugate

  描述了一种容易的合成方法，用于π-膨胀的四硫富瓦烯衍生物。3,6-二氯哒嗪稠合的四硫富富烯的Suzuki反应与苯基硼酸 或者 联苯硼酸给出了一系列新颖的T形有机π共轭物。通过循环伏安法和紫外可见光谱法的结合，对缀合物的电子性质进行了实验研究。它们的HOMO和LUMO能级估计约为-5 eV和-3.2 eV，分别是p沟道和n沟道场效应晶体管中的空气工作稳定性范围。经验证，只有一个带有较长烷基链的共轭物（n = 1，R = n -C 18 H 37）能在介晶相中自组装成层状结构，其薄膜器件的最佳载流子迁移率是4.5 ×10 -5 cm 2 V -1 s -1。