2,5-bis(10-hexyl-10H-phenothiazin-3-yl)thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2,5-bis(10-hexyl-10H-phenothiazin-3-yl)thiophene
• 英文别名: 10-Hexyl-3-[5-(10-hexylphenothiazin-3-yl)thiophen-2-yl]phenothiazine；10-hexyl-3-[5-(10-hexylphenothiazin-3-yl)thiophen-2-yl]phenothiazine
• 化学式: C₄₀H₄₂N₂S₃
• 分子量: 646.985
• InChiKey: BOOWOIXDUQTVGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-bromo-10-hexyl-10H-phenothiazine 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 水 为溶剂， 反应 60.0h， 生成 2,5-bis(10-hexyl-10H-phenothiazin-3-yl)thiophene
  参考文献：
  名称：

  First synthesis and electronic properties of (hetero)aryl bridged and directly linked redox active phenothiazinyl dyads and triads

  摘要：

  Phenothiazinyl dyads and triads with variable functionalization can be synthesized in good yields by Suzuki coupling with suitable phenothiazinyl boronates. In addition, the structure of the phenylated phenothiazine (6) has been corroborated by an X-ray structure analysis. According to cyclic voltammetry these oligofunctional heterocyclic oligomers are strongly electronically coupled and represent suitable functional units for novel redox active molecular wires. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01848-2

文献信息

• Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties
  作者：Dominik Urselmann、Konstantin Deilhof、Bernhard Mayer、Thomas J J Müller

  DOI：10.3762/bjoc.12.194

  日期：——

  The pseudo five-component Sonogashira-Glaser cyclization synthesis of symmetrically 2,5-diaryl-substituted thiophenes is excellently suited to access thienyl-bridged oligophenothiazines in a one-pot fashion. Three thienyl-bridged systems were intensively studied by UV-vis and fluorescence spectroscopy as well as by cyclic voltammetry. The oxidation proceeds with lower oxidation potentials and consistently

  对称的2,5-二芳基取代的噻吩的假五组分Sonogashira-Glaser环化合成非常适合以单锅方式访问噻吩基桥接的低聚吩噻嗪。通过紫外-可见光谱和荧光光谱以及循环伏安法深入研究了三个噻吩桥联系统。氧化以较低的氧化电位进行，并且可以识别出始终可逆的氧化。斯托克斯位移很大，可以测量大量的荧光量子产率。计算化学表明，具有S形和螺旋结构的最低能量构象异构体，与低聚吩噻嗪类似。
• Luminescent, Redox-Active Diphenothiazine Dumbbells Expanded by Conjugated Arenes and Heteroarenes
  作者：Martina Hauck、Raluca Turdean、Karin Memminger、Jan Schönhaber、Frank Rominger、T. J. J. Müller

  DOI：10.1021/jo101997t

  日期：2010.12.17

  Dumbbell-shaped diphenothiazines bridged by conjugatively linked (hetero)aromatic moieties were synthesized in a modular fashion by Suzuki-Miyaura coupling in good yields. The electronic structure was studied by DFT computations, determining the geometry optimized lowest energy conformers and scrutinizing the Kohn-Sham FMOs. The torsional deviation from coplanarity is predominantly influencing the electronic structure, i.e., by deviation from ideal overlap and maximal electron transmission. The reversible oxidation potentials assigned to the phenothiazinyl electrophores in most cases can thereby be qualitatively rationalized. All dumbbell-shaped diphenothiazines are strongly luminescent, which can be attributed to extended pi-electron conjugation with considerable excited state electronic coupling as a consequence of large structural and electronic distributional changes upon photoexcitation.