4,4',4'',4'''-tetra-(4-pentenoxymethyl)-2,2',5',5'',2'',2'''-quaterthiazole | 535993-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,4',4'',4'''-tetra-(4-pentenoxymethyl)-2,2',5',5'',2'',2'''-quaterthiazole
• CAS: 535993-87-4
• 化学式: C₃₆H₄₆N₄O₄S₄
• 分子量: 727.05
• InChiKey: CNACVHOMFHUPKP-UHFFFAOYSA-N

物化性质

• 沸点：
  811.2±75.0 °C(predicted)
• 密度：
  1.177±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.44
• 重原子数：
  48.0
• 可旋转键数：
  27.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  88.48
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4,4',4'',4'''-tetra-(4-pentenoxymethyl)-2,2',5',5'',2'',2'''-quaterthiazole 在 9-硼双环[3.3.1]壬烷 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到4,4',4'',4'''-tetra-(5-hydroxypentyloxymethyl)-2,2',5',5'',2'',2'''-quaterthiazole
  参考文献：
  名称：

  Intermolecular Interactions in π-Stacked Conjugated Molecules. Synthesis, Structure, and Spectral Characterization of Alkyl Bithiazole Oligomers

  摘要：

  Syntheses are reported of new 4,4'-dialkyl-2,2'-bithiazole oligomers that have alkenoxy side chains that are capable of easy conversion to oligomers with functionalized side chains, e.g., terminally substituted hydroxy chains. The crystal structures of two representative oligomers (4,4',4",4"'-tetra-(2-propenoxymethyl)2,2',5',5",2",2"'-quaterthiazole (3132) and 4,4',4",4"'-tetra-(3-hydroxypropyloxymethyl)-2,2',5',5",2",2"'quaterthiazole (3H2)) were determined; 3P2 crystallizes in a pi-stacked motif with two molecules per unit cell, whereas 3H2 forms pi-stacks that are linked with hydrogen bonds to form infinite two-dimensional sheets with one molecule per unit cell. A comparison of the UV-vis spectra of the compounds in solution and in the solid state provides unequivocal evidence for the presence of a Davyclov splitting, W-D approximate to 0.2 eV, in solid 3P2. The spectra are interpreted in the framework of molecular exciton theory to extract a value of the intermolecular transfer integral, J approximate to 0.2 eV, for a total exciton bandwidth of ca. 0.8 eV. Monte Carlo calculations were used to determine the density of states of the exciton band and the absorption and emission line shapes of the 0 <-- 0 transition. It is suggested that the "three-humped" absorption profile typical of partially crystalline, regioregular polymers is the "optical signature" of pi-stacking.

  DOI：

  10.1021/ja029216m
• 作为产物：
  描述：

  4,4'-Bis(chloromethyl)-2,2'-bi-1,3-thiazole 在 正丁基锂 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 6.0h， 生成 4,4',4'',4'''-tetra-(4-pentenoxymethyl)-2,2',5',5'',2'',2'''-quaterthiazole
  参考文献：
  名称：

  Intermolecular Interactions in π-Stacked Conjugated Molecules. Synthesis, Structure, and Spectral Characterization of Alkyl Bithiazole Oligomers

  摘要：

  Syntheses are reported of new 4,4'-dialkyl-2,2'-bithiazole oligomers that have alkenoxy side chains that are capable of easy conversion to oligomers with functionalized side chains, e.g., terminally substituted hydroxy chains. The crystal structures of two representative oligomers (4,4',4",4"'-tetra-(2-propenoxymethyl)2,2',5',5",2",2"'-quaterthiazole (3132) and 4,4',4",4"'-tetra-(3-hydroxypropyloxymethyl)-2,2',5',5",2",2"'quaterthiazole (3H2)) were determined; 3P2 crystallizes in a pi-stacked motif with two molecules per unit cell, whereas 3H2 forms pi-stacks that are linked with hydrogen bonds to form infinite two-dimensional sheets with one molecule per unit cell. A comparison of the UV-vis spectra of the compounds in solution and in the solid state provides unequivocal evidence for the presence of a Davyclov splitting, W-D approximate to 0.2 eV, in solid 3P2. The spectra are interpreted in the framework of molecular exciton theory to extract a value of the intermolecular transfer integral, J approximate to 0.2 eV, for a total exciton bandwidth of ca. 0.8 eV. Monte Carlo calculations were used to determine the density of states of the exciton band and the absorption and emission line shapes of the 0 <-- 0 transition. It is suggested that the "three-humped" absorption profile typical of partially crystalline, regioregular polymers is the "optical signature" of pi-stacking.

  DOI：

  10.1021/ja029216m