2-[(5-(5-dimethyl(isothiocyanatomethyl)silyl)thien-2-yl)thien-2-yl]-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide

• 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: 2-[(5-(5-dimethyl(isothiocyanatomethyl)silyl)thien-2-yl)thien-2-yl]-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide
• 英文别名: [5-[5-(5,9-Dimethyl-7,7-dioxo-3,7lambda6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl)thiophen-2-yl]thiophen-2-yl]-(isothiocyanatomethyl)-dimethylsilane；[5-[5-(5,9-dimethyl-7,7-dioxo-3,7λ6,11-trithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl)thiophen-2-yl]thiophen-2-yl]-(isothiocyanatomethyl)-dimethylsilane
• 化学式: C₂₂H₁₉NO₂S₆Si
• 分子量: 549.88
• InChiKey: JNTSSDFRHLOOFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-bromo-3,5-dimethyl-dithieno[2,3-d:3',2'-b]thiophene-4,4-dioxide 在 tetrakis(triphenylarsine)palladium(0) 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 18.0h， 生成 2-[(5-(5-dimethyl(isothiocyanatomethyl)silyl)thien-2-yl)thien-2-yl]-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide
  参考文献：
  名称：

  Rigid-Core Fluorescent Oligothiophene-S,S-dioxide Isothiocyanates. Synthesis, Optical Characterization, and Conjugation to Monoclonal Antibodies

  摘要：

  In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.

  DOI：

  10.1021/jo026298o

文献信息

• Rigid-Core Fluorescent Oligothiophene-<i>S</i>,<i>S</i>-dioxide Isothiocyanates. Synthesis, Optical Characterization, and Conjugation to Monoclonal Antibodies
  作者：Giovanna Sotgiu、Massimo Zambianchi、Giovanna Barbarella、Fabio Aruffo、Franco Cipriani、Alfredo Ventola

  DOI：10.1021/jo026298o

  日期：2003.2.1

  In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.