2,6-diphenyl-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide | 379692-11-2

• 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: 2,6-diphenyl-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide
• 英文别名: DTTO；5,9-Dimethyl-4,10-diphenyl-3,7lambda6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene 7,7-dioxide；5,9-dimethyl-4,10-diphenyl-3,7λ6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene 7,7-dioxide
• CAS: 379692-11-2
• 化学式: C₂₂H₁₆O₂S₃
• 分子量: 408.566
• InChiKey: YAKHVIZSJFFTDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-溴-4-甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 、 双(三丁基锡)硫醚 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 39.5h， 生成 2,6-diphenyl-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide
  参考文献：
  名称：

  Live-Cell-Permeant Thiophene Fluorophores and Cell-Mediated Formation of Fluorescent Fibrils

  摘要：

  In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives' (DTTOs). that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of Other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

  DOI：

  10.1021/ja2065522

文献信息

• Facilitated synthesis of functional oligothiophenes for application in thin film devices and live cell imaging
  作者：Francesca DiMaria、Giovanna Barbarella

  DOI：10.1080/17415993.2013.807810

  日期：2013.12.1

  This paper describes recent developments in the synthesis of ultrapure functional oligothiophene-based materials taking advantage of enabling techniques such as microwave/ultrasound irradiation and chitosan-supported palladium catalysts. Examples showing how ultrapure oligothiophenes self-organize in order to optimize charge transport in thin film devices and fluorescence emission inside living cells are reported.[GRAPHICS].