9,10-bis(benzimidazol-1-ylmethyl)anthracene | 1196989-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(benzimidazol-1-ylmethyl)anthracene
• 英文别名: 9,10-bis{(benzimidazol)methyl}anthracene；9,10-bis((1H-benzo[d]imidazol-1-yl)methyl)anthracene；9,10-Bis((1h-benzo[d]imidazol-1-yl)methyl)anthracene；1-[[10-(benzimidazol-1-ylmethyl)anthracen-9-yl]methyl]benzimidazole
• CAS: 1196989-85-1
• 化学式: C₃₀H₂₂N₄
• 分子量: 438.531
• InChiKey: WNSJMNSXKORJPA-UHFFFAOYSA-N

物化性质

• 沸点：
  745.2±70.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)palladium(II) tetrafluoroborate 、 9,10-bis(benzimidazol-1-ylmethyl)anthracene 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  自组装的Pd2L4笼，可选择性地包裹硝酸盐

  摘要：

  由四个蒽桥联的苯并咪唑配体和两个PdII离子自组装一个具有D4对称性的M2L4笼。笼子上有一个简洁的疏水性口袋，被蒽壁包裹着。

  DOI：

  10.1039/c5cc07306e
• 作为产物：
  描述：

  苯并咪唑 、 9,10-二(氯甲基)蒽 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 9,10-bis(benzimidazol-1-ylmethyl)anthracene
  参考文献：
  名称：

  1-(2-Naphthalenyl)benzimidazolium based fluorescent probe for acetate ion in 90% aqueous buffer

  摘要：

  A new fluorescent probe 9,10-bis[1-(2-naphthalenylbenzimidazolium)-3-methyl]anthracene 1 has been synthesized which shows highly selective fluorescence quenching with only acetate ions in 90% aqueous buffer at pH 7.4. The structure optimization (DFT) of probe 1 and its 1:1 complex with acetate anion, shows that probe 1 is pre-organized and has to undergo minimal spatial reorganization during complexation with acetate anion. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.084

文献信息

• Supramolecular Organic Frameworks (SOFs) Using Anthracene Based Flexible Azoles: Synthesis, Structural and Photophysical Studies
  作者：Udai P. Singh、Neetu Singh、Aurobinda Mohanty、Ray J. Butcher

  DOI：10.1007/s10870-020-00831-8

  日期：2021.3

  A series of salts viz., BIA.2SIA.2CH3OH (1a), BTA.NDS.2H2O (1b), BTA.NDS.2H2O.2DMF (1c), BBIA.0.5NDS.DMF (1d), BBIA.2SIA.2H2O (1e) and BPA.NDS.2H2O (1f) have been synthesised by solvothermal method. All these salts were characterized by elemental analysis, TGA, PXRD and single-crystal X-ray diffraction technique. Structural analysis revealed that these salts showed N–H⋯O, O–H⋯O, C–H⋯O, C–H⋯π and π⋯π interactions. The overall percentage of short contacts and the contribution of the different intermolecular interactions were examined by Hirshfeld surface analysis. The solid-state emission maxima of all salts is blue-shifted in comparison to the pure ligand. This may due to different modes of packing of anthracene moieties and solvent assisted hydrogen bonding in sulfonate salts. Thermal stability of 1d, 1e and 1f salts are more than other salts. Hirshfeld surface analysis employed to identify intermolecular interactions within the structure. The close inspection of Hirshfeld surface analysis of NDS and SIA molecule in all the structures revealed that the maximum area of the Hirshfeld surface are covered by O⋯H/H⋯O hydrogen bond interaction in all salts

  通过溶热法合成了一系列盐，即 BIA.2SIA.2CH3OH (1a)、BTA.NDS.2H2O (1b)、BTA.NDS.2H2O.2DMF (1c)、BBIA.0.5NDS.DMF (1d)、BBIA.2SIA.2H2O (1e) 和 BPA.NDS.2H2O (1f)。所有这些盐都通过元素分析、热重分析、PXRD 和单晶 X 射线衍射技术进行了表征。结构分析表明，这些盐表现出 N-H⋯O、O-H⋯O、C-H⋯O、C-H⋯π 和 π⋯π 相互作用。Hirshfeld 表面分析法检测了短接触的总体比例和不同分子间相互作用的贡献。与纯配体相比，所有盐的固态发射最大值都发生了蓝移。这可能是由于磺酸盐中蒽分子的不同包装模式和溶剂辅助氢键所致。1d、1e 和 1f 盐的热稳定性高于其他盐。利用 Hirshfeld 表面分析来确定结构中的分子间相互作用。对所有结构中 NDS 和 SIA 分子的 Hirshfeld 表面分析表明，在所有盐中，O⋯H/H⋯O 氢键相互作用覆盖了 Hirshfeld 表面的最大面积。
• Cadmium coordination polymers based on flexible bis(imidazole) ligands: A rare example for doublet of doublet cadmium polyhedron arrangements
  作者：Chatla Naga Babu、Paladugu Suresh、Natarajan Sampath、Ganesan Prabusankar

  DOI：10.1016/j.molstruc.2014.06.074

  日期：2014.10

  Two one-dimensional (1D) coordination polymers, [LCd(O2NO)(2)(DMF)(2)}(2)(LCd(O2NO)(2)(DMF))(DMF)}(2)](n) (1) and [L'Cd(O2NO)(ONO2)(DMF)(2)](n) (2), having an aryl chromophoric unit and a flexible bis(imidazole) tail, 9,10-bis(benzimidazol)methyl}anthracene (L) and 1,4-bis(imidazol)methyl}benzene (L'), with various coordination modes have been obtained. Molecule 1 represents the first structurally characterized one dimensional coordination polymer consisting of both hepta- and octa-coordinated cadmium centers. In 1, two distorted pentagonal bipyramidal Cd(II) centers and two distorted triangular dodecahedral Cd(II) centers are alternately arranged via bridging bidentate N,N-chelating ligand, L. Whereas, a distorted pentagonal bipyramidal Cd(II) center is formed in 2 where the sterically less crowded If serves as a bridging bidentate N,N-chelating ligand. Furthermore, 1 and 2 have been characterized by elemental analysis, FT-IR, H-1 NMR, UV-vis and fluorescent techniques. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis and Anion Sensing of Water-Soluble Metallomacrocycles
  作者：Liao-Yuan Yao、Lin Qin、Ting-Zheng Xie、Yi-Zhi Li、Shu-Yan Yu

  DOI：10.1021/ic200047t

  日期：2011.7.4

  The self-assembly of (TMEDA)Pd(NO(3))(2) or (TMEDA)Pt(NO(3))(2) (where TMEDA = N(1),N(1),N(2),N(2)-tetramethylethane-1,2-diamine) and anthracene- or ferrocene-based diimidazole ligands (L(1-3)) in aqueous solution affords a series of positively charged [M(2)L(2)](4+) dimetallomacrocycles. Their structures were characterized by (1)H NMR and electrospray ionization mass spectrometry and in the cases of [(TMEDA)Pd](2)L(2)(1)}(NO(3))(4) (1), [(TMEDA)Pd](2)L(2)(1)}(PF(6))(4) (1a), and [(TMEDA)Pd](2)L(2)(3)}(NO(3))(4) (4) by single-crystal X-ray diffraction analysis. Interestingly, the NMR spectra of 1 and la revealed that the difference of their structures, as confirmed by X-ray diffraction analysis, was that a NO(3)(-) of 1 was encapsulated inside the cavity of the basket-shaped metallomacrocycle by C-H center dot center dot center dot O hydrogen bonds, while PF(6)(-) of 1a was bound outside by C-H center dot center dot center dot F hydrogen bonds. The fluorescence titration experiment exhibited the formation of 1:1 host guest complexation for anthracene-based positively charged [M(2)L(2)](4+)-type metallomacrocycles with NO(3)(-). The interactions between metallomacrocycles and various anions were investigated via fluorescence titration and cyclic voltammetry studies, respectively.
• 1-(2-Naphthalenyl)benzimidazolium based fluorescent probe for acetate ion in 90% aqueous buffer
  作者：Sandeep Kumar、Prabhpreet Singh、Subodh Kumar

  DOI：10.1016/j.tetlet.2012.02.084

  日期：2012.4

  A new fluorescent probe 9,10-bis[1-(2-naphthalenylbenzimidazolium)-3-methyl]anthracene 1 has been synthesized which shows highly selective fluorescence quenching with only acetate ions in 90% aqueous buffer at pH 7.4. The structure optimization (DFT) of probe 1 and its 1:1 complex with acetate anion, shows that probe 1 is pre-organized and has to undergo minimal spatial reorganization during complexation with acetate anion. (c) 2012 Elsevier Ltd. All rights reserved.
• A self-assembled Pd₂L₄ cage that selectively encapsulates nitrate
  作者：Li-Peng Zhou、Qing-Fu Sun

  DOI：10.1039/c5cc07306e

  日期：——

  A M2L4 cage with D4 symmetry was self-assembled from four anthracene-bridged benzimidazole ligands and two PdII ions. The cage features a concise hydrophobic pocket wrapped up by the anthracene walls...

  由四个蒽桥联的苯并咪唑配体和两个PdII离子自组装一个具有D4对称性的M2L4笼。笼子上有一个简洁的疏水性口袋，被蒽壁包裹着。