chlorodimethyl(E,E)-(1,2,3,4-tetraphenyl-1,3-butadien-1-yl)tin | 99643-58-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: chlorodimethyl(E,E)-(1,2,3,4-tetraphenyl-1,3-butadien-1-yl)tin
• CAS: 99643-58-0
• 化学式: C₃₀H₂₇ClSn
• 分子量: 541.707
• InChiKey: ZCHHPWSKRUTCRY-PGXPKDKISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  chlorodimethyl(E,E)-(1,2,3,4-tetraphenyl-1,3-butadien-1-yl)tin 在 溴 作用下， 以 四氯化碳 为溶剂， 生成 1-Brom-1,2,3,4-tetraphenyl-cis,cis-butadien-(1,3)
  参考文献：
  名称：

  Tetraphenylcyclobutadiene Derivatives. III. Preparation of Precursors and Some Preliminary Investigations

  摘要：

  DOI：

  10.1021/jo01054a002
• 作为产物：
  描述：

  1,4-dilithio-1,2,3,4-tetraphenylbutadiene 在 ethanol 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 chlorodimethyl(E,E)-(1,2,3,4-tetraphenyl-1,3-butadien-1-yl)tin
  参考文献：
  名称：

  硼酸芳烃系统。第 8 部分。硼环多烯中环状共轭的物理和化学后果。五芳基硼的抗芳香性

  摘要：

  五取代硼或硼环戊二烯已通过两种途径制备：(1) (E&)-(1,2,3,4-四芳基-1,3-丁二烯-1,4-亚基)二锂在醚溶液中与芳基(二卤)硼烷形成硼醚醚合物；(2) 1,1-二烷基-2,3,4,5-四芳基锡酚在非供体介质中的交换反应生成未溶剂化的硼。硼是出乎意料的强路易斯酸，与胺甚至醚和腈络合，并且非常容易发生氧化、溶剂分解和 Diels-Alder 反应。上述化学行为，连同它们不寻常的核磁和电子光谱特性，可以直接解释为 4-*-电子硼环戊二烯核的 Hiickel 反芳香特性。通过将这种核作为受扰的环戊二烯基 7r 系统处理，可以获得对光谱和化学性质的定性理解。从这些考虑，很明显，三配位硼的 2p,-轨道和四碳丁二烯基阵列之间的共轭是不稳定的，并且是硼的高反应性的来源。$-杂化硼原子可能会形成带有 sp2 杂化碳阵列的环状共轭系统，因为硼的共价半径 (0.80 A) 和 Allred-Rochow

  DOI：

  10.1021/ja00263a006

文献信息

• Electrochemical and Photophysical Properties of a Series of Group-14 Metalloles
  作者：Justin Ferman、Joseph P. Kakareka、Wim T. Klooster、Jerome L. Mullin、Joseph Quattrucci、John S. Ricci、Henry J. Tracy、William J. Vining、Scott Wallace

  DOI：10.1021/ic980662d

  日期：1999.5.1

  A series of six group-14 dimethyl- or diphenyl-tetraphenylmetallacyclopentadienes were synthesized and characterized by their spectroscopic and electrochemical properties. The group-14 elements investigated were silicon, germanium, and tin. (The compounds are designated according to the heteroatom and the substituent on the heteroatom, i.e., SiMe, SiPh, ..., SnPh.) Five of the six compounds luminesce in both the solid state and in solution. The emission maxima of SiPh, GePh, and SnPh are invariant to a change in the heteroatom, while for SiMe, GeMe, and SnMe there is a strong dependence of the emission maxima on the identity of the heteroatom. SiMe emits at a longer wavelength than GeMe, while SnMe is not luminescent. The dramatic luminescence difference between the two tin compounds was investigated. C-13 NMR coupling to Sn-119/117, observed in both SnMe and SnPh, was used to make C-13 NMR resonance assignments. Qualitative results of semiempirical molecular orbital calculations support the C-13 NMR assignments. The crystal structure data for SnPh was obtained at 20 degrees C: a = 10.353(2) Angstrom, b = 16.679(2) Angstrom, c = 9.482(1) Angstrom, alpha = 99.91(1)degrees, beta = 106.33(1)degrees, gamma = 77.80(1)degrees with Z = 2 in space group . It is proposed that the increased electron density at tin in SnMe is responsible for the deactivation of the emissive state. The presence of phenyl substituents in SnPh serves to stabilize the emissive state and luminescence is observed.