9-(5-iodothiophen-2-yl)-9H-carbazole | 916915-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(5-iodothiophen-2-yl)-9H-carbazole
• CAS: 916915-76-9
• 化学式: C₁₆H₁₀INS
• 分子量: 375.233
• InChiKey: BHWKVQYLJVVZQK-UHFFFAOYSA-N

物化性质

• 沸点：
  485.1±45.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  9-(5-iodothiophen-2-yl)-9H-carbazole 、 [5-ethynyl-15-(4-nitrophenylethynyl)-10,20-bis(3,5-bis(3,3-dimethyl-1-butyloxy)phenyl)porphinato]zinc(II) 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到[5-(2-(9H-carbazol-9-yl)thiophen-5-yl-ethynyl)-15-(4-nitrophenylethynyl)-10,20-bis(3,5-bis(3,3-dimethyl-1-butyloxy)phenyl)porphinato]zinc(II)
  参考文献：
  名称：

  Electronic Modulation of Hyperpolarizable (Porphinato)zinc(II) Chromophores Featuring Ethynylphenyl-, Ethynylthiophenyl-, Ethynylthiazolyl-, and Ethynylbenzothiazolyl-Based Electron-Donating and -Accepting Moieties

  摘要：

  A series of conjugated (porphinato)zinc(II)-based chromophores structurally related to [5-(4-dimethylaminophenylethynyl)-15-( 5-nitrothienyl-2-ethynyl)-10,20-bis(3,5-bis(3,3-dimethyl-1-butyloxy)phenyl)porphinato]zinc(II) were synthesized using metal-catalyzed cross-coupling reactions involving [5-bromo-15-triisopropylsilylethynyl-10,20-diarylporphinato] zinc(II), [5-bromo-15-(4-dimethylaminophenylethynyl)-10,20-diarylporphinato]zinc(II), [5-(4-dimethylaminophenylethynyl)15- ethynyl-10,20-diarylporphinato]zinc(II), and [5-(4-nitrophenylethynyl)-15-ethynyl-10,20-diarylporphinato] zinc(II), along with appropriately functionalized aryl, thienyl (or thiophenyl), thiazolyl, benzothiazolyl, and carbazolyl precursors. The linear and nonlinear optical properties of these asymmetrically 5,15-substitued( 10,20-diarylporphinato)zinc(II) chromophores that bear either 2-(9H-carbazol-9-yl)-thiophen-5-yl-ethynyl, 4-dimethylaminophenylethynyl, or 2-(N, N-diphenylamino)thiophen-5-yl-ethynyl electron-releasing groups and an electron withdrawing group selected from 2-formyl-thiophen-5-yl-ethynyl, 2-(2,2-dicyanovinyl)-thiophen-5-yl-ethynyl, 4-nitrophenylethynyl, 6-nitrobenzothiazol-2-yl-ethynyl, or 5-nitrothiazol-2-yl-ethynyl are reported. The dynamic hyperpolarizabilities of these compounds were determined from hyper-Rayleigh light scattering measurements carried out at a fundamental incident irradiation wavelength (lambda(inc)) of 1300 nm; these measured beta(1300) values ranged from 690 -> 1400 x 10(-30) esu. These data (i) show that these neutral dipolar molecules express substantial beta(1300) values, (ii) highlight that reductions in the magnitude of the aromatic stabilization energy of (porphinato) metal-pendant arylethynyl groups have a significant impact upon the magnitude of the molecular hyperpolarizability, and (iii) provide insights into advantageous design modifications for closely related structures having potential utility in long-wavelength electrooptic applications.

  DOI：

  10.1021/ic060898e