2-(4'-(methylthio)phenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole | 1159194-94-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4'-(methylthio)phenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole
• 英文别名: 1,3-Diethyl-2-[2-(4-methylsulfanylphenyl)ethynyl]-1,3,2-benzodiazaborole
• CAS: 1159194-94-1
• 化学式: C₁₉H₂₁BN₂S
• 分子量: 320.266
• InChiKey: UTPMJSHFKYJPQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  31.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-bromo-1,3-diethyl-1,3,2-benzodiazaborole 、 p-methylthiophenylethynyllithium 以 四氢呋喃 为溶剂， 生成 2-(4'-(methylthio)phenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole
  参考文献：
  名称：

  UV-Photoelectron Spectroscopic Studies on 2-Arylethynyl-1,3,2-benzodiazaboroles

  摘要：

  Gas-phase He 1 photoelectron spectra of a series of 2-arylethynyl-1,3,2-benzodiazaboroles BEP-X [1 (X = H), 2 (X = Me), 3 (X = OMe), 4 (X = SMe), 5 (X = NMe2), 6 (X = Br)] have been recorded and assessed by density functional theory calculations. The first ionization energies of these benzodiazaboroles are in the order 5 (7.0 eV) < 3 (7.15 eV) < 2 (7.2 eV) < 1 = 4 = 6 (7.3 eV). As an important result of this study it was disclosed that in contrast to the remaining diazaboroles the frontier orbitals of the amino derivative 5 lack contributions from the diazaborole part of the molecule. In keeping with this, the dipole moment of the ground state (5.51 D) is only slightly changed, to 6.60 D, upon electronic excitation. This also rationalizes the low Stokes shift of 2600 cm(-1) in comparison to the other diazaboroles in this study (5900-7300 cm(-1)).

  DOI：

  10.1021/om100352c

文献信息

• Synthetic, structural, photophysical and computational studies on 2-arylethynyl-1,3,2-diazaboroles
  作者：Lothar Weber、Vanessa Werner、Mark A. Fox、Todd B. Marder、Stefanie Schwedler、Andreas Brockhinke、Hans-Georg Stammler、Beate Neumann

  DOI：10.1039/b821208b

  日期：——

  are largely aryl in character for all compounds. Thus, in contrast to other conjugated systems containing three-coordinate boron centers such as B(Mes)(2), (Mes = 2,4,6-Me(3)C(6)H(2)), in which the boron serves as a pi-acceptor, the 10-pi electron benzodiazaborole moiety appears to function as a pi-donor moiety.

  新的2-芳基炔基苯并-1,3,2-二氮杂硼烷，2-（4'-XC（6）H（4）C [三键，长度为m-破折号] C）-1,3-Et（2） -1,3,2-N（2）BC（6）H（4）（X = Me; MeO; MeS; Me（2）N）由B-溴二氮杂硼酸酯2-Br-1,3-制备Et（2）-1,3,2-N（2）BC（6）H（4），带有适当的锂化芳基乙炔，ArC 3键，长度为m-CLi。和的分子结构通过X射线衍射研究确定。对这些diazaboroles的紫外可见光谱和发光光谱研究表明，强烈的蓝/紫荧光具有非常大的量子产率，为0.89-0.99。实验结果得到DFT和TD-DFT计算的补充。相对于5900-7300 cm（-1）范围内的斯托克斯位移，仅2600 cm（-1）的斯托克斯位移由（X = H）所发现的不同电子结构部分地解释了。HOMO主要位于其中的二氮杂硼烯丙基中的芳基上，而对于所有化合物而言，L