5,5'-bis(4,4'-dinonyl-2,2'-bithiazol-5-yl)-3,4,3',4'-bis(ethylenedioxy)-2,2'-dithienyl | 1000843-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-bis(4,4'-dinonyl-2,2'-bithiazol-5-yl)-3,4,3',4'-bis(ethylenedioxy)-2,2'-dithienyl
• 英文别名: 4-Nonyl-5-[5-[7-[4-nonyl-2-(4-nonyl-1,3-thiazol-2-yl)-1,3-thiazol-5-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]-2-(4-nonyl-1,3-thiazol-2-yl)-1,3-thiazole；4-nonyl-5-[5-[7-[4-nonyl-2-(4-nonyl-1,3-thiazol-2-yl)-1,3-thiazol-5-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl]-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]-2-(4-nonyl-1,3-thiazol-2-yl)-1,3-thiazole
• CAS: 1000843-64-0
• 化学式: C₆₀H₈₆N₄O₄S₆
• 分子量: 1119.76
• InChiKey: MPNZVHMLKZNKIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.4
• 重原子数：
  74
• 可旋转键数：
  37
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  230
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  5-trimethylstannyl-4,4'-dinonyl-2,2'-bithiazole 、 5,5'-dibromo-2,2'-bis(3,4-ethylenedioxythiophene) 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 生成 5,5'-bis(4,4'-dinonyl-2,2'-bithiazol-5-yl)-3,4,3',4'-bis(ethylenedioxy)-2,2'-dithienyl
  参考文献：
  名称：

  Side Chain Disorder and Phase Transitions in Alkyl-Substituted, Conjugated Oligomers. Relation to Side-Chain Melting in P3ATs

  摘要：

  Certain 4,4'-alkyl substituted 2,2'-bithiazole and bithiazole-thiophene oligomers display an endothermic transition in their DSC trace below their respective melting points. Variable-temperature FTIR, MAS-H-1 NMR, UV-vis spectra, and XRD all indicate that the thermal transition is due to a crystal-crystal phase transition that we have labeled alpha -> beta. FTIR shows a stepwise increase in the concentration of gauche defects at the alpha -> beta transition temperature, but MAS NMR spectra show little increase in the side chain motion until the mp is reached. UV-vis spectra demonstrate that the conjugated main chains remain essentially planar through the alpha -> beta transition, and significant deviations from planarity occur only at higher temperatures, but well below the mp. The close similarity of this behavior to the phase transitions in long chain n-paraffins and the "side-chain melting" phenomenon in poly(3-alkylthiophenes), P3ATs, suggests that the latter may actually be more accurately described as a crystal-crystal phase transition of the crystalline fraction, driven by side chain disorder.

  DOI：

  10.1021/ja076235t

文献信息

• Side Chain Disorder and Phase Transitions in Alkyl-Substituted, Conjugated Oligomers. Relation to Side-Chain Melting in P3ATs
  作者：M. David Curtis、John I. Nanos、Hyunsik Moon、Woong Sang Jahng

  DOI：10.1021/ja076235t

  日期：2007.12.1

  Certain 4,4'-alkyl substituted 2,2'-bithiazole and bithiazole-thiophene oligomers display an endothermic transition in their DSC trace below their respective melting points. Variable-temperature FTIR, MAS-H-1 NMR, UV-vis spectra, and XRD all indicate that the thermal transition is due to a crystal-crystal phase transition that we have labeled alpha -> beta. FTIR shows a stepwise increase in the concentration of gauche defects at the alpha -> beta transition temperature, but MAS NMR spectra show little increase in the side chain motion until the mp is reached. UV-vis spectra demonstrate that the conjugated main chains remain essentially planar through the alpha -> beta transition, and significant deviations from planarity occur only at higher temperatures, but well below the mp. The close similarity of this behavior to the phase transitions in long chain n-paraffins and the "side-chain melting" phenomenon in poly(3-alkylthiophenes), P3ATs, suggests that the latter may actually be more accurately described as a crystal-crystal phase transition of the crystalline fraction, driven by side chain disorder.