2-(5-bromothiophen)imidazo[4,5-f][1,10]phenanthroline | 1332651-09-8

• 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-(5-bromothiophen)imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(5-bromothiophen-2-yl)imidazo[4,5-f ]-[1,10]phenanthroline；2-(5-bromothiophen-2-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1332651-09-8
• 化学式: C₁₇H₉BrN₄S
• 分子量: 381.255
• InChiKey: ZNQGMKXYWKYEDA-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: methanol (67-56-1))
• 沸点：
  654.2±65.0 °C(Predicted)
• 密度：
  1.727±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-bromothiophen)imidazo[4,5-f][1,10]phenanthroline 在 盐酸 、 sodium perchlorate monohydrate 作用下， 以 水 为溶剂， 反应 96.0h， 以60%的产率得到[H(5-Br-TIP)](ClO₄)(H₂O)₂
  参考文献：
  名称：

  Comparative structural and spectral analyses for mononuclear and dinuclear metal complexes of 2-thiophen and 2-(5-bromothiophen) imidazo[4,5-f][1,10]phenanthroline

  摘要：

  一系列具有不同金属/配体摩尔比 (1 : 1) 的单核和双核汞 (I)、汞 (II)、镍 (II)、镧 (III)、亚铁 (II) 和钌 (II) 配合物 4–11 ，1 : 2 和 1 : 3)，具有 2-噻吩咪唑[4,5-f[[1,10[菲咯啉 (TIP)] 和 2-(5-溴噻吩)咪唑[4,5-f][1,10 [菲咯啉 (5-Br-TIP) 配体已被合成并进行结构比较。此外，本文描述了 TIP 和 5-Br-TIP (1-3) 与 PF6- 和 ClO4- 抗衡离子的三种质子化盐，其中发现质子位于 1,10-菲咯啉的氮原子之一上部分。值得注意的是，双核汞（I）和镍（II）配合物6和7的整个分子分别在2.52和2.90 nm的长度上表现出优异的平面性。配体 TIP 和 5-Br-TIP、质子化盐 1-3 和金属配合物 4-11 的 UV-Vis、1H NMR 和发光光谱也进行了研究和比较。

  DOI：

  10.1039/c2ce26001h
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 2-(5-bromothiophen)imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  N-烷基化策略可保持寡聚噻吩/咪唑/ 1,10-菲咯啉基杂环半导体和荧光化合物的分子平面性

  摘要：

  平面低聚噻吩/咪唑/ 1,10-菲咯啉（OTIP）基的杂环，芳族，半导体和荧光化合物，带有N-取代的烷基链（烯丙基，n-丁基，n-辛基，n-十二烷基和n-cetyl）已经过设计和合成。它们都具有特定的N配位位点，各种供体-受体间隔基，良好的分子平面性，合适的溶解度和较高的热稳定性。与噻吩环的常规双β-烷基化相比，我们的研究结果表明，用于OTIP的单咪唑N-烷基化策略除了提高溶解度外，还具有保持整个分子平面性的优势，这一点可以清楚地证明由八个X射线单晶结构中相邻的噻吩/咪唑/ 1,10-菲咯啉（TIP）环之间的小二面角决定。特别是，正十二烷基和正十六烷基取代的OTIP（7和8）具有相同的2.37 nm分子长（M W＝ 939和1052），具有良好的分子平面性，上述二面角为8.9（5）和10.4（5）°。此外，特别注意了到七个对称OTIPs（理化性质6 - 8，13 - 15，和19），包括在

  DOI：

  10.1002/asia.201402851

文献信息

• Aggregation-induced emission generation via simultaneous N-alkylation and rhenium(I) tricarbonyl complexation for 2-(2-thienyl)imidazo[4,5-f][1,10]-phenanthroline
  作者：Hua-Qi Liu、Yu-Xin Peng、Yi Zhang、Xi-Qiang Yang、Fan-Da Feng、Xu-Biao Luo、Liu-Shui Yan、Bin Hu、Wei Huang

  DOI：10.1016/j.dyepig.2019.108074

  日期：2020.3

  In this paper, imidazole N-alkylation (allyl and n-butyl) and the following rhenium(I) complexation strategy have been used for 2-(2-thienyl)imidazo[4,5-f][1,10]-phenanthroline (TIP) to generate two aggregation-induced emission (AIE) active rhenium(I) tricarbonyl complexes Re2 and Re3. The destroy of planarity and conjugation of TIP by introducing alkyl chains and the increase of steric hindrance via

  在本文中，咪唑N-烷基化（烯丙基和正丁基）和以下rh（I）络合策略已用于2-（2-噻吩基）咪唑并[4,5- f ] [1,10]-菲咯啉（TIP）生成两个聚集诱导发射（AIE）活性active（I）三羰基配合物Re2和Re3。通过引入烷基链破坏TIP的平面性和结合以及通过植入八面体Re（I）配位球增加空间位阻导致分子内旋转受到限制以及分子间π-π堆积的形成，这可能是产生这种现象的主要原因AIE激活。Re1和Re2的X射线单晶结构引入空间拥挤的烯丙基后，验证TIP骨架中的二面角从10.8（5）o增大到22.7（1）o以及不同的晶体堆积方式（AAAA与ABAB）。进一步的研究表明，上述同时修饰对于AIE的产生至关重要，因为对照实验表明，无论是单个咪唑N-烷基化（L2和L3）还是单个rh（I）三羰基络合物（Re1）都会引起典型的聚集-引起荧光猝灭。据我们所知，这是有关Re（I）-TIP配合物和用
• Electronic Effect of Substituents on the DNA Intercalation of Ruthenium(II)Polypyridyl Complexes
  作者：Chang-Ge Zheng、Chun-Lei Ma、Xiao-Wei Yu、Qian-Li Qian、Yang Song、Jun Kong、Yan Xu

  DOI：10.1002/cbdv.201000336

  日期：2011.8

  photophysical and DNA‐binding properties were investigated by means of UV and fluorescence spectroscopic methods and viscosity measurements, respectively. The results suggest that all five complexes can bind to CT‐DNA with various binding strength. Complexes 2 and 3 showed the strongest and the weakest binding affinity, respectively, among these five complexes. Due to the substituent position of the

  五种钌(II)配合物，即[Ru(bpy)2(TIP)]2+ (bpy=2,2'-联吡啶；TIP=2-噻吩咪唑并[4,5-f] [1,10]菲咯啉； 1), [Ru(bpy)2(5-NTIP)]2+ (5-NTIP=2-(5-nitrothiophen)imidazo[4,5-f] [1,10]phenaNThroline; 2), [Ru( bpy)2(5-MOTIP)]2+ (5-MOTIP=2-(5-甲氧基噻吩)咪唑并[4,5-f] [1,10]菲咯啉；3), [Ru(bpy)2(5- BTIP)]2+ (5-BTIP=2-(5-溴噻吩)咪唑并[4,5-f] [1,10]菲咯啉；4)，和[Ru(bpy)2(4-BTIP)]2+ (4-BTIP=2-(4-溴噻吩)咪唑并[4,5-f] [1,10]菲咯啉；5)，通过元素分析和UV/VIS、IR和1H-NMR光谱方法合成和表征. 分别通过紫
• Multicolor (Vis-NIR) mesoporous silica nanospheres linked with lanthanide complexes using 2-(5-bromothiophen)imidazo[4,5-f][1,10]phenanthroline for in vitro bioimaging
  作者：Ying Liu、Lining Sun、Jinliang Liu、Yu-Xin Peng、Xiaoqian Ge、Liyi Shi、Wei Huang

  DOI：10.1039/c4dt02444c

  日期：——

  Using the modified phenanthroline ligand, the multicolor mesoporous silica nanospheres linked with lanthanide complexes were synthesized and characterized, and the application for cell imaging has been studied.

  使用改良的菲啰啉配体，合成并表征了与镧系络合物相连的多色介孔二氧化硅纳米球，并研究了其在细胞成像方面的应用。
• Dual topoisomerase I and II poisoning by chiral Ru(II) complexes containing 2-thiophenylimidazo[4,5-f][1,10]phenanthroline derivatives
  作者：Yu-Chuan Wang、Chen Qian、Zai-Li Peng、Xiao-Juan Hou、Li-Li Wang、Hui Chao、Liang-Nian Ji

  DOI：10.1016/j.jinorgbio.2013.09.015

  日期：2014.1

  A series of chiral Ru(II) complexes bearing thiophene ligands were synthesized and characterized. Both Ru(II) complexes Delta/Lambda-[Ru(bpy)(2)(pscl)](2+) (Delta/Lambda-1) and Delta/Lambda-[Ru(bpy)(2)(psbr)](2+) (Delta/Lambda-2) (bpy = 2,2'-bipyridine, pscl = 2(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline, psbr = 2-(5-bromothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline) showed antitumor activities against A549, HepG2 and BEL-7402 tumor cell lines, especially HeLa tumor cell line. Moreover, Delta enantiomers were more active than Lambda enantiomers, accounting for the different cellular uptake. In addition, with the extension of time, these enantiomers could finally accumulate in the nucleus, suggesting that nucleic acids were the cellular target of these enantiomers. The DNA-binding behaviors of complexes were studied using spectroscopic and viscosity measurements. Results suggested that four complexes could bind to DNA in an intercalative mode but no obvious DNA-binding selectivity between the enantiomers was observed. Topoisomerase inhibition and DNA religation assay confirmed that four complexes acted as efficient dual topoisomerase I and II poisons, DNA strand breaks had also been observed from alkaline single cell gel electrophoresis (comet assay). Delta-1 and Delta-2 inhibited the growth of HeLa cells through the induction of apoptotic cell death, as evidenced by the Alexa Fluor (R) 488 annexin V staining assays and flow cytometry analysis. The results demonstrated that Delta/Lambda-1 and Delta/Lambda-2 acted as dual topoisomerase I and II poisons and caused DNA damage that could lead to cell cycle arrest by apoptosis. (C) 2013 Elsevier Inc. All rights reserved.
• Luminescent lanthanide(III)-cored complexes based on the combination of 2-(5-bromothiophen)imidazo[4,5-f][1,10]phenanthroline and 2-thenoyltrifluoroacetonate ligands
  作者：Qian-Qian Liu、Jiao Geng、Xiao-Xu Wang、Ke-Hua Gu、Wei Huang、You-Xuan Zheng

  DOI：10.1016/j.poly.2013.04.036

  日期：2013.8

  A family of ternary beta-diketonate lanthanide(III)-cored complexes based on the combination of 2-(5-bromothiophen)imidazo[4,5-f] [1,10] phenanthroline (5-Br-TIP)/2-thiophenimidazo[4,54][1,10]phenanthroline (TIP) and 2-thenoyltrifluoroacetonate (TTA) ligands have been described herein, i.e. Ln(TTA)(3)(5-Br-TIP) [Ln = Eu (1), Dy (2), Er (3), Tb (4), Sm (5), Yb (6)] and Eu(ITA)(3)(TIP) (7). According to the fluorescence spectra of complexes 1, 3, 5, 6 and 7, characteristic luminescence of the Ln(3+) ions in the visible and near-infrared band ranges is observed, which is attributed to efficient energy transfer from the ligands to the metal centers. The room-temperature luminescence intensity of 7 is analogous to that of the strong fluorescent complex Eu(TTA)(3)(phen), but the fluorescence intensity of 1 is much weaker. In addition, complexes 1 and 7 show 1.1 and 1.4 times greater fluorescence intensity at 77 K compared with the fluorescence spectra at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.