4,4'-di(trimethylsilyl)-2,2'-bipyridine | 1372805-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4'-di(trimethylsilyl)-2,2'-bipyridine
• 英文别名: 4,4'-Bis(trimethylsilyl)-2,2'-bipyridine；trimethyl-[2-(4-trimethylsilylpyridin-2-yl)pyridin-4-yl]silane
• CAS: 1372805-52-1
• 化学式: C₁₆H₂₄N₂Si₂
• 分子量: 300.551
• InChiKey: KCWAUZLBROLSPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(三甲基甲硅烷基)吡啶 在 sodium 、 水 作用下， 以 四氢呋喃 、 paraffin oil 为溶剂， 以69%的产率得到4,4'-di(trimethylsilyl)-2,2'-bipyridine
  参考文献：
  名称：

  钠分散吡啶脱氢二聚合成 2,2'-联吡啶

  摘要：

  2,2'-联吡啶衍生物是通过使用钠分散体对未活化的吡啶进行脱氢二聚反应合成的。该反应具有操作简单、条件温和以及使用地球上储量丰富且无毒的钠作为唯一金属源的特点。重要的是，不需要过渡金属，这在材料科学和药物合成领域是有益的，因为过渡金属的污染可能会导致重大问题。

  DOI：

  10.1055/a-2047-8355

文献信息

• Silane: A new linker for chromophores in dye-sensitised solar cells
  作者：Katherine Szpakolski、Kay Latham、Colin Rix、Rozina A. Rani、Kourosh Kalantar-zadeh

  DOI：10.1016/j.poly.2012.07.078

  日期：2013.3

  A series of ruthenium(II) polypyridyl complexes, with novel silane functionalisation, [Ru(bipy)(2)(bipy-sil)] (PF6)(2) (3), [Ru(bipy-sil)(2)Cl-2] (6), and [Ru(bipy-sil)(2)(NCS)(2)] (7) have been synthesised and tested as chromophores (dyes) in TiO2 and WO3 based dye-sensitised solar cells (DSSCs). The performance of the respective DSSCs were compared to analogous dyes with ionic carboxylate ([Ru(bipy)(2)(dcbipy)](PF6)(2) (1), [Ru(dcbipy)(2)Cl-2] (4), [Ru(dcbipy)(2)(NCS)(2)] (5)) or phosphonate ([Ru(bipy)(2)(dpipy)](PF6)(2) (2)) linking groups. The covalent silane-metal oxide linkage offers much needed improvement to the operating conditions, and lifetime of DSSCs, in terms of pH range and choice of solvent. UV-Vis spectroscopy of the deep-red solutions showed that the bis-bipy-sil complexes absorbed more visible light than the tris-bipy complex, as indicated by the presence of two absorption bands and higher E values. The UV-Vis spectrum of (3) contained a single broad absorption at 400-600 nm with: lambda(max) = 457 nm; epsilon = 10520 +/- 440 L mol(-1) cm(-1), whereas two intense broad absorption bands were observed for novel bis-bipy-sil complexes (6): 340-370 nm (lambda(max(1)) = 365 nm, epsilon((1)) = 12716 +/- 180 L mol(-1) cm(-1)); and 440-540 nm (lambda(max(2)) = 485 nm, epsilon((2)) = 11070 +/- 150 L mol(-1) cm(-1)), and (7): 340-400 nm (lambda(max) = 371 nm epsilon((1)) = 20690 +/- 485 L mol(-1) cm(-1)), and 460-530 nm (lambda(max) = 500 nm and epsilon((2)) = 20750 +/- 487 L mol(-1) cm(-1)). The bands in (7) being significantly more defined.A 10-fold improvement in the efficiency of the bipy-sil TiO2-based DSSCs was observed from (3) to (6) to (7). This performance was lower than that of the commercial N3 dye, [Ru(dcbipy)(2)(NCS)(2)] (5), but the current of (7) on WO3, was comparable to that of the carboxylate system (4). There is considerable potential for further improvement by modification of the silyl linker, reducing the long non-conjugated propyl chain between the amide group and the silatrane (bipy-sil), to a short, conjugated link. During an extensive synthetic study, the most promising strategy was identified as direct linkage, the formation of a direct Si-C bond, using butyllithium with 4,4'-dibromo-2,2'-bipyridine and either trimethylsilane or 1-ethoxysilatrane, provided that the product can be captured and stabilised prior to binding to a metal oxide coated DSSC substrate. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 2,2’-Bipyridines via Dehydrogenative Dimerization of Pyridines Using Sodium Dispersion
  作者：Pinaki Bhusan De、Laurean Ilies、Kazuhiko Takai、Sobi Asako

  DOI：10.1055/a-2047-8355

  日期：——

  2,2′-Bipyridine derivatives were synthesized by dehydrogenative dimerization of nonactivated pyridines using sodium dispersion. The reaction features operational simplicity, mild conditions, and the use of earth abundant and nontoxic sodium as the sole metal source. Importantly, transition metals are not required, which is beneficial in the fields of materials science and drug synthesis, where the

  2,2'-联吡啶衍生物是通过使用钠分散体对未活化的吡啶进行脱氢二聚反应合成的。该反应具有操作简单、条件温和以及使用地球上储量丰富且无毒的钠作为唯一金属源的特点。重要的是，不需要过渡金属，这在材料科学和药物合成领域是有益的，因为过渡金属的污染可能会导致重大问题。