4-bromo-7-(4-hexylthiophen-2-yl)benzo[c][1,2,5]selenadiazole | 1526919-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4-bromo-7-(4-hexylthiophen-2-yl)benzo[c][1,2,5]selenadiazole
• CAS: 1526919-68-5
• 化学式: C₁₆H₁₇BrN₂SSe
• 分子量: 428.254
• InChiKey: FDPGAILXAHGMPX-UHFFFAOYSA-N

物化性质

• 沸点：
  482.3±55.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-bromo-7-(4-hexylthiophen-2-yl)benzo[c][1,2,5]selenadiazole 在 四(三苯基膦)钯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 27.0h， 生成 (E)-1,2-bis(7-(4-hexyl-5-(trimethylstannyl)thiophen-2-yl)benzo[c][1,2,5]selenadiazol-4-yl)ethene
  参考文献：
  名称：

  Bis(benzoselenadiazol)ethane: A π‐Extended Acceptor‐Dimeric Unit for Ambipolar Polymer Transistors with Hole and Electron Mobilities Exceeding 10 cm2 V−1 s−1

  摘要：

  The lack of ambipolar polymers with balanced hole (μh) and electron mobilities (μe) >10 cm2 V−1 s−1 is the main bottleneck for developing organic integrated circuits. Herein, we show the design and synthesis of a π‐extended selenium‐containing acceptor‐dimeric unit, namely benzo[c][1,2,5]selenadiazol‐4‐yl)ethane (BBSeE), to address this dilemma. In comparison to its sulfur‐counterpart, BBSeE demonstrates enlarged co‐planarity, selective noncovalent interactions, polarized Se−N bond, and higher electron affinity. The successful stannylation of BBSeE offers a great opportunity to access acceptor‐acceptor copolymer pN‐BBSeE, which shows a narrower band gap, lower‐lying lowest unoccupied molecular orbital level (−4.05 eV), and a higher degree of backbone planarity. Consequently, the pN‐BBSeE‐based organic transistors display an ideally balanced ambipolar transporting property with μh and μe of 10.65 and 10.72 cm2 V−1 s−1, respectively. To the best of our knowledge, the simultaneous μh/μe values >10.0 cm2 V−1 s−1 are the best performances ever reported for ambipolar polymers. In addition, pN‐BBSeE shows an excellent shelf‐storage stability, retaining over 85 % of the initial mobility values after two months storage. Our study demonstrates the π‐extended acceptor‐dimeric BBSeE is a promising acceptor building block for constructing high‐performance ambipolar polymers applied in next‐generation organic integrated circuit.

  DOI：

  10.1002/anie.202400061
• 作为产物：
  描述：

  3-己基噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-bromo-7-(4-hexylthiophen-2-yl)benzo[c][1,2,5]selenadiazole
  参考文献：
  名称：

  Benzoselenadiazole Fluorescent Probes – Near-IR Optical and Ratiometric Fluorescence Sensor for Fluoride Ion

  摘要：

  A highly selective and sensitive near-IR optical sensor, benzoselenadiazole based diarylamine (TBS-HN), for fluoride (F-) has been designed and synthesized. TBS-HN also shows turn-on ratiometric fluorescence signaling in the presence of F- by inhibiting the excited state intramolecular proton transfer (ESIPT) processes.

  DOI：

  10.1021/ol403082p