2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene
• 英文别名: 2,5-bis(2,2-di(thiophen-2-yl)vinyl)thiophene；2,5-Bis(2,2-dithiophen-2-ylethenyl)thiophene；2,5-bis(2,2-dithiophen-2-ylethenyl)thiophene
• 化学式: C₂₄H₁₆S₅
• 分子量: 464.721
• InChiKey: BYOWBPXZKQNVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene 以 氘代氯仿 为溶剂， 反应 25.0h， 以28%的产率得到7,11-di(thien-2-yl)trithia[5]helicene
  参考文献：
  名称：

  Formation of a trithia[5]helicene in an unexpected photoreaction of a methyl-substituted bis(dithienylethenyl)thiophene through a double sequence of 6π-electrocyclization/aromatization (dehydrogenation/demethylation)

  摘要：

  Photochemical reactions of 2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene (1a) and its tetramethyl derivative 1b, under direct photoexcitation, and photoinduced electron-transfer conditions, were studied. Our initial prediction was that 1b would undergo a photoreaction as part of a reversible photochromic system, while a reaction of its non-methyl substituted analog 1a would undergo a typical double sequence of 6 pi-electrocyclization (6 pi-EC)/aromatization (AR) (double dehydrogenation, -2H) to give 7,11-di(thien-2-yl)trithia[5]helicene (2a). In fact, we observed that photoirradiation of 1b leads to formation of the 7,11-bis(3-methylthien-2-yl)trithia[5]helicene (2b). In this process, 2b is formed via a double sequence of 6 pi-EC/AR (dehydrogenation/demethylation, -H/-Me). Moreover, the yield of formation of 2b is much higher than that of 2a, which reacts through a double sequence of 6 pi-EC/AR (-2H). Thus, this photochemically-induced paradoxical cascade reaction based on the newly uncovered reactivity serves as an efficient method to construct the trithia[5]helicene framework. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.10.012
• 作为产物：
  描述：

  2,5-双(氯甲基)噻吩 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 40.0h， 生成 2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene
  参考文献：
  名称：

  Formation of a trithia[5]helicene in an unexpected photoreaction of a methyl-substituted bis(dithienylethenyl)thiophene through a double sequence of 6π-electrocyclization/aromatization (dehydrogenation/demethylation)

  摘要：

  Photochemical reactions of 2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene (1a) and its tetramethyl derivative 1b, under direct photoexcitation, and photoinduced electron-transfer conditions, were studied. Our initial prediction was that 1b would undergo a photoreaction as part of a reversible photochromic system, while a reaction of its non-methyl substituted analog 1a would undergo a typical double sequence of 6 pi-electrocyclization (6 pi-EC)/aromatization (AR) (double dehydrogenation, -2H) to give 7,11-di(thien-2-yl)trithia[5]helicene (2a). In fact, we observed that photoirradiation of 1b leads to formation of the 7,11-bis(3-methylthien-2-yl)trithia[5]helicene (2b). In this process, 2b is formed via a double sequence of 6 pi-EC/AR (dehydrogenation/demethylation, -H/-Me). Moreover, the yield of formation of 2b is much higher than that of 2a, which reacts through a double sequence of 6 pi-EC/AR (-2H). Thus, this photochemically-induced paradoxical cascade reaction based on the newly uncovered reactivity serves as an efficient method to construct the trithia[5]helicene framework. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.10.012

文献信息

• Aggregation‐Induced and Polymorphism‐Dependent Thermally Activated Delayed Fluorescence (TADF) Characteristics of an Oligothiophene: Applications in Time‐Dependent Live Cell Multicolour Imaging
  作者：Samir Kumar Sarkar、Meenakshi Pegu、Santosh Kumar Behera、Siva Krishna Narra、Pakkirisamy Thilagar

  DOI：10.1002/asia.201901138

  日期：2019.12.13

  architecture have been exploited for constructing thermally activated delayed fluorescence (TADF) materials. Herein, we report the first example of a thiophene-based thermally activated delayed fluorescent molecule without a D-A architecture. Compound 1 (2,5-bis(2,2-di(thiophen-2-yl)vinyl)thiophene) is conformationally flexible and shows weak fluorescence in the solution state but displays bright TADFin

  通常，具有扭曲的供体-受体（DA）结构的分子已被用于构建热激活的延迟荧光（TADF）材料。在此，我们报道了没有DA结构的基于噻吩的热激活延迟荧光分子的第一个例子。化合物1（2,5-双（2,2-二（噻吩-2-基）乙烯基）噻吩）具有构象柔性，在溶液状态下显示弱荧光，但在稠合和固态下均显示明亮的TADF。化合物1结晶为两种不同的多晶型物（1a和1b）。有趣的是，两种多晶型物均显示出截然不同的TADF特征。对于活细胞随时间变化的多色（绿色，黄色和红色）成像，已经探究了1的宽光谱特征和TADF特征。