1,1-diethynyl-2,3,4,5-tetraphenyl-1-sila-2,4-cyclopentadiene | 68558-79-2

• 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-diethynyl-2,3,4,5-tetraphenyl-1-sila-2,4-cyclopentadiene
• 英文别名: 1,1-diethynyl-2,3,4,5-tetraphenylsilole；1,1-diethynyl-2,3,4,5-tetraphenyl-1H-silole
• CAS: 68558-79-2
• 化学式: C₃₂H₂₂Si
• 分子量: 434.612
• InChiKey: GVXNXSUERQKYDV-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 沸点：
  589.2±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  33
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,4-dilithio-1,2,3,4-tetraphenylbutadiene 在 四氯化硅 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 72.0h， 生成 1,1-diethynyl-2,3,4,5-tetraphenyl-1-sila-2,4-cyclopentadiene
  参考文献：
  名称：

  Preparation of oligomers containing tetraphenylsilole, acetylene and aromatic groups in the main chain, and incorporation of iron carbonyl

  摘要：

  Polycarbosilanes with the structure [-SiR2-C=C-Z-C=C]n (R2Si = 2,3,4,5-tetraphenyl-1-sila-2,4-cyclopentadiene; Z = 1,4-benzene, 4,4'-biphenyl, 9,10-anthracene, 2,7-fluorene, 2,5- and 2,6-pyridine, 6,6'-bipyridine, 2.5-thiophene. 2,6-p-dimethylaminonitrobenzene 2,6-p-nitroaniline, 2,6-p-nitrophenol, and 2,7-fluoren-9-one) were prepared by reaction of 1,1-diethynyl-2,3,4,5-tetraphenyl-1-sila-2,4-cyclopentadiene with the appropriate (hetero)aromatic dibromide or diiodide in the presence of [(PPh3)2PdCl2] and CuI. Exo- and endotherms observed in the initial DSC scans were absent in repeat scans. The oligomer where Z = p-C6H4 reacted with [Fe(CO)5] under UV irradiation to give an oligomer containing iron carbonyl fragments attached to ca. 30% of the silole groups.

  DOI：

  10.1016/0022-328x(93)83313-k

文献信息

• Hyperbranched Poly(phenylenesilolene)s:  Synthesis, Thermal Stability, Electronic Conjugation, Optical Power Limiting, and Cooling-Enhanced Light Emission
  作者：Junwu Chen、Han Peng、Charles C. W. Law、Yuping Dong、Jacky W. Y. Lam、Ian D. Williams、Ben Zhong Tang

  DOI：10.1021/ma034012r

  日期：2003.6.1

  Silole-containing hyperbranched polyphenylenes (1) are synthesized, which exhibit high thermal stability, extended electronic conjugation, excellent optical power limiting performance, and novel cooling-enhanced photoluminescence. The homopolycyclotrimerization of 1,1-diethynyl-2,3,4,5-tetraphenylsilole (2) and its copolycyclotrimerizations with 1-octyne catalyzed by TaCl5-Ph4Sn proceed smoothly at room temperature and produce completely soluble polymers in high yields (up to similar to85%). The molecular structures of 1 are characterized by spectroscopic analyses. The thermal stability of 1 is evaluated by thermogravimetric analyses, which detect virtually no weight losses when the polymers are heated to similar to300 degreesC. The hyperbranched polyphenylenes are electronically conjugated, as suggested by their strong absorption in the visible spectral region (lambda(max) similar to 520 nm). Because of this extended electronic conjugation, polymers 1 are nonlinear optically active and strongly attenuate the optical power of intense laser pulses, whose optical limiting performances are superior to that of C-60, the best-known optical limiter. The photoluminescence of the polymers is dramatically enhanced by cooling their solutions to low temperatures. This unique phenomenon of cooling-enhanced emission is probably caused by the restricted intramolecular rotations of the phenyl rings upon the axes of the single bonds linked to the silole cores at the cryogenic temperatures.
• BACHEBA N. A.; GAVRILOVA O. N.; SLADKOV A. M., IZV. AN CCCP. CEP. XIM., 1978, HO 9, 2149-2151
  作者：BACHEBA N. A.、 GAVRILOVA O. N.、 SLADKOV A. M.

  DOI：——

  日期：——