2,9-Bis(2,2'-bithien-5-yl)-1,10-phenanthroline | 211501-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2,9-Bis(2,2'-bithien-5-yl)-1,10-phenanthroline
• 英文别名: 2,9-Bis(5-thiophen-2-ylthiophen-2-yl)-1,10-phenanthroline；2,9-bis(5-thiophen-2-ylthiophen-2-yl)-1,10-phenanthroline
• CAS: 211501-55-2
• 化学式: C₂₈H₁₆N₂S₄
• 分子量: 508.712
• InChiKey: JCCDJHZNWXGBHD-UHFFFAOYSA-N

物化性质

• 沸点：
  695.6±50.0 °C(predicted)
• 密度：
  1.400±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 6,9,12,15,18,21-Hexaoxa-35,38-diazahexacyclo[24.8.4.22,5.222,25.029,37.032,36]dotetraconta-1(35),2(42),3,5(41),22(40),23,25(39),26(38),27,29(37),30,32(36),33-tridecaene 、 2,9-Bis(2,2'-bithien-5-yl)-1,10-phenanthroline 以 二氯甲烷 、 乙腈 为溶剂， 以95%的产率得到[Cu(2,9-bis(2,2'-bithien-5-yl)-1,10-phenanthroline)(C12H6N2(C6H4(OCH2CH2)5OC6H4))]BF4
  参考文献：
  名称：

  Conjugated polyrotaxanes containing coordinating units: reversible copper(I) metallation–demetallation using lithium as intermediate scaffolding

  摘要：

  通过铜(I)模板和电聚合合成了一种含有共轭主链的新型聚轮烷； CuI 解络后，只有在铜去除过程中存在锂的情况下才可能进行重金属化，因为不稳定的支架能够防止自由配位位点和有机基质的塌陷。

  DOI：

  10.1039/a708662h
• 作为产物：
  描述：

  1,10-菲罗啉 以 四氢呋喃 、 甲苯 为溶剂， 生成 2,9-Bis(2,2'-bithien-5-yl)-1,10-phenanthroline
  参考文献：
  名称：

  π共轭配体聚合物缠绕在铜中心附近

  摘要：

  我们描述了与交替的α-四噻吩基（poly [Cu（T2）2]）或3'，4'，3''''，4''''-四己基-α-六氢噻吩基（poly [Cu （T3）2]）部分和1,10-菲咯啉络合位点。我们的策略是合成2,9-双（低聚噻吩基）-1,10-菲咯啉前体，然后通过Cu1模板组装这些配体，然后进行电聚合。聚[Cu（T2）2]对Cu氧化还原中心和共轭骨架显示出单独的电活性，而在聚[Cu（T3）2]的情况下，电活性重叠。在这两种情况下，对处于还原态的这些聚合物在Cu-K边缘进行的X射线吸收研究确定，四个氮原子是最接近的铜（I）邻居。对于聚[Cu（T2）2]，Cu1环境是扭曲的四面体，类似于单体模型化合物，但空间约束的数量略高。聚[Cu（T3）2]的Cu1环境是畸变较少的四面体，具有异常短的Cu1-N平均键长。去除聚[Cu（T2）2]中的Cu1会导致结构不可逆转的塌陷，而Cu1结合的可逆性对于聚[Cu

  DOI：

  10.1002/(sici)1521-3765(20000502)6:9<1663::aid-chem1663>3.3.co;2-h

文献信息

• Conjugated Polyrotaxanes Incorporating Mono- or Divalent Copper Complexes
  作者：Pierre-Louis Vidal、Bernadette Divisia-Blohorn、Gérard Bidan、Jean-Marc Kern、Jean-Pierre Sauvage、Jean-Louis Hazemann

  DOI：10.1021/ic990516n

  日期：1999.9.1

  A conjugated polyrotaxane poly[Cu(1.2)(+)] has been synthesized via copper(I)-templated strategy and electropolymerization. The polymer backbone contains alternating quaterthiophene moieties and 1,10-phenanthroline complexes. It is threaded by coordinating cyclic units. Copper(I) binding was reversible only if lithium cation was present during copper removal, as a labile scaffolding, maintaining the topography of the free coordinating sites and of the organic matrix, as demonstrated by H-1 NMR studies on monomer precursors. Electrochemistry has been coupled with X-ray absorption spectroscopy at the Cu K edge to study the interactions between the complexed copper centers and the conjugated backbone. The spectra of poly[Cu(1.2)(n+)] in various oxidation states have been analyzed and compared with those of monomeric model compounds. For all of the samples four nitrogen atoms are the closest neighbors. No dramatic geometric and electronic differences exist between monomeric and polyrotaxane Cu(I) binding sites. However, for the copper(I) rotaxane the closest neighbors were unambiguously split into two subshells of two nitrogen atoms, reflecting higher steric constraints around the copper center in the polymetallorotaxane. For the divalent complexed copper-rotaxane, these steric constraints partially prevent the flattening of the coordination tetrahedron expected when passing from Cu(I) to Cu(II) and the Cu(II)-N distances are significantly longer in the polymer (2.04 Angstrom) than in the model compound (2.00 Angstrom).
• π-Conjugated Ligand Polymers Entwined around Copper Centres
  作者：Pierre-Louis Vidal、Bernadette Divisia-Blohorn、Gérard Bidan、Jean-Louis Hazemann、Jean-Marc Kern、Jean-Pierre Sauvage

  DOI：10.1002/(sici)1521-3765(20000502)6:9<1663::aid-chem1663>3.3.co;2-h

  日期：2000.5.2

  overlap in the case of poly[Cu(T3)2]. An X-ray absorption study on these polymers in their reduced state at the Cu-K edge identifies, in both cases, four nitrogen atoms as the closest copper(I) neighbours. For poly[Cu(T2)2], the Cu1 environment is a distorted tetrahedron similar to a monomer model compound, but with a slightly higher number of steric constraints. The Cu1 environment for poly[Cu(T3)2]

  我们描述了与交替的α-四噻吩基（poly [Cu（T2）2]）或3'，4'，3''''，4''''-四己基-α-六氢噻吩基（poly [Cu （T3）2]）部分和1,10-菲咯啉络合位点。我们的策略是合成2,9-双（低聚噻吩基）-1,10-菲咯啉前体，然后通过Cu1模板组装这些配体，然后进行电聚合。聚[Cu（T2）2]对Cu氧化还原中心和共轭骨架显示出单独的电活性，而在聚[Cu（T3）2]的情况下，电活性重叠。在这两种情况下，对处于还原态的这些聚合物在Cu-K边缘进行的X射线吸收研究确定，四个氮原子是最接近的铜（I）邻居。对于聚[Cu（T2）2]，Cu1环境是扭曲的四面体，类似于单体模型化合物，但空间约束的数量略高。聚[Cu（T3）2]的Cu1环境是畸变较少的四面体，具有异常短的Cu1-N平均键长。去除聚[Cu（T2）2]中的Cu1会导致结构不可逆转的塌陷，而Cu1结合的可逆性对于聚[Cu
• Conjugated polyrotaxanes containing coordinating units: reversible copper(I) metallation–demetallation using lithium as intermediate scaffolding
  作者：P. L. Vidal、M. Billon、B. Divisia-Blohorn、G. Bidan、P. L. Vidal、B. Divisia-Blohorn、J. M. Kern、J. P. Sauvage

  DOI：10.1039/a708662h

  日期：——

  A new polyrotaxane containing a conjugated backbone has been synthesized via a copper(I) template and electropolymerisation; after decomplexation of CuI, remetallation is only possible if lithium is present during copper removal, as labile scaffolding able to prevent collapse of the free coordination sites and of the organic matrix.

  通过铜(I)模板和电聚合合成了一种含有共轭主链的新型聚轮烷； CuI 解络后，只有在铜去除过程中存在锂的情况下才可能进行重金属化，因为不稳定的支架能够防止自由配位位点和有机基质的塌陷。