1,1-dihydroxy-2,3,4,5-tetraphenyl-1H-silole | 389631-49-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1-dihydroxy-2,3,4,5-tetraphenyl-1H-silole
• 英文别名: 1,1-dihydroxyl-2,3,4,5-tetraphenylsilole；1,1-dihydroxo-2,3,4,5-tetraphenylsilole；1,1-dihydroxy-2,3,4,5-tetraphenylsilole；1,1-Dihydroxy-2,3,4,5-tetraphenylsilole
• CAS: 389631-49-6
• 化学式: C₂₈H₂₂O₂Si
• 分子量: 418.567
• InChiKey: NACUXHXFDXUVEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-二氯-1,1,3,3,-四甲基二硅氧烷 、 1,1-dihydroxy-2,3,4,5-tetraphenyl-1H-silole 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以10%的产率得到1-(1,4-(1,2,3,4-tetramethyl-1,3-butadiene))-3,3,5,5-tetraphenyl cyclotrisiloxane
  参考文献：
  名称：

  AEE-active cyclic tetraphenylsilole derivatives with ∼100% solid-state fluorescence quantum efficiency

  摘要：

  含有亮度高的四苯基硅烷基环硅氧烷，发射波长为500纳米，固态荧光量子产率约为100%。

  DOI：

  10.1039/c5dt01846c
• 作为产物：
  描述：

  1,1-dichloro-2,3,4,5-tetraphenyl-1H-silole 在 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 1,1-dihydroxy-2,3,4,5-tetraphenyl-1H-silole
  参考文献：
  名称：

  高荧光二喹纳丁酮铝硅烷衍生物的合成

  摘要：

  荧光二合一化合物：将强发射体，二喹纳丁酮铝和良好的电子传输剂四苯基甲硅烷混合在一起，产生了高荧光化合物，这些化合物有望成为不需要掺杂剂的发光器件的候选者（见图）。

  DOI：

  10.1002/chem.201300728

文献信息

• High solid-state fluorescence in ring-shaped AEE-active tetraphenylsilole derivatives
  作者：Yuanjing Cai、Kerim Samedov、Haley Albright、Brian S. Dolinar、Ilia A. Guzei、Rongrong Hu、Chaocan Zhang、Ben Zhong Tang、Robert West

  DOI：10.1039/c4cc06203e

  日期：——

  Three ring-shaped AEE-active silole-containing compounds were synthesized by mild condensation reactions. Cyclotrisiloxane compound 1 displays high solid-state quantum yield (Φfl = 0.86) with the fluorescence maximum at 512 nm. This high fluorescence efficiency results mainly from decreased vibrational pathways to fluorescence decay due to the intramolecular C–H⋯π interactions.

  通过温和的缩合反应合成了三种环状 AEE 活性含噻咯化合物。环三硅氧烷化合物 1 显示出高固态量子产率 (Φfl = 0.86)，荧光最大值位于 512 nm。这种高荧光效率主要是由于分子内 C-H⋯π 相互作用导致荧光衰减的振动路径减少。
• Observation of Negative Charge Trapping and Investigation of Its Physicochemical Origin in Newly Synthesized Poly(tetraphenyl)silole Siloxane Thin Films
  作者：Jin-Kyu Choi、Seunghyun Jang、Ki-Jeong Kim、Honglae Sohn、Hyun-Dam Jeong

  DOI：10.1021/ja1108112

  日期：2011.5.25

  A new kind of organic inorganic hybrid polymer, poly(tetraphenyl)silole siloxane, was invented and synthesized for realization of its unique charge trap properties. The organic portions consisting of (tetraphenyl)silole rings were responsible for negative charge trapping, while the Si-O-Si inorganic linkages provided the intrachain energy barrier for controlling electron transport. The polysilole siloxane dielectric thin films were fabricated by spin-coating and curing of the polymers, followed by characterization with spectroscopic ellipsometry (SE), near edge X-ray absorption fine structure spectroscopy (NEXAFS), and photoemission spectroscopy (PES). The abrupt increase in density and decrease in thickness of the thin film at a curing temperature of 100 degrees C was attributed to a thermodynamically preferred state in the nanoscopic arrangement of the polymer chains; this was due to cofacial pi-pi interactions in a skewed manner between peripheral phenyl groups of the (tetraphenyl)silole rings of the adjacent polymer chains. Using the NEXAFS spectrum to assess high electron affinity, the LUMO energy level of the dielectric thin film cured at 150 degrees C was positioned 1 eV above the Fermi energy level (E-F). The electron trapping of the dielectric thin films was confirmed from the positive flat band shift (Delta V-FB) in the capacitance-voltage (C-V) measurements performed within the metal-insulator-semiconductor (MIS) device structure, which strongly verified the polymer design concept. From the simple kinetics model of the electron transport, it was proposed that the flat band shift (Delta V-FB) or trap density of the negative charges (vertical bar rho vertical bar) was logarithmically proportional to the decay constant (beta) for the electron-tunneling process. When a phenyl group of a silole ring in a polymer chain was inserted into the two available phenyl groups of another silole ring in another polymer chain, the electron transfer between the groups was enhanced, decreasing the trap density of the negative charges (vertical bar rho vertical bar). For the thermodynamically preferred state generating the high refractive index, the distance between the two phenyl groups of the adjacent polymer chains was estimated to be in the range of 0.27-0.36 nm.
• Synthesis and High Solid-State Fluorescence of Cyclic Silole Derivatives
  作者：Yuanjing Cai、Kerim Samedov、Brian S Dolinar、Zhegang Song、Ben Zhong Tang、Chaocan Zhang、Robert West

  DOI：10.1021/om500884b

  日期：2015.1.12

  Cyclotetrasiloxanes 13 containing different silole-based fluorogenic units (silafluorene, 1,3-diphenyl-9-silafluorene, tetraphenylsilole) were synthesized by cohydrolysis and condensation reactions. Their optical properties in solution and as crystals were studied. These compounds have low quantum yields in solution (Phi(fl) = 0.01-0.18) with fluorescence maxima at 359-375 nm for silafluorene-containing compounds 1 and 3 and at 491 nm for AEE-active tetraphenylsilole compound 2. However, 13 have high solid-state quantum yields (Phi(fl) = 0.65-0.78) with fluorescence maxima at 377-390 nm for compounds 1 and 3 and at 517 nm for tetraphenylsilole- and silafluorene-containing compound 2. Packing analysis of 13 in the crystal structure and MO and excited-state calculations were performed to explore possible fluorescence mechanisms in these compounds.