N²,N^2'-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1'-biphenyl]-2,2'-dicarboxamide | 1431380-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N²,N^2'-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1'-biphenyl]-2,2'-dicarboxamide
• 英文别名: N²,N^2′-bis[(1H-benzimidazol-2-yl)methyl]biphenyl-2,2′-dicarboxamide；N-(1H-benzimidazol-2-ylmethyl)-2-[2-(1H-benzimidazol-2-ylmethylcarbamoyl)phenyl]benzamide
• CAS: 1431380-85-6
• 化学式: C₃₀H₂₄N₆O₂
• 分子量: 500.56
• InChiKey: BUEODNNFIYBMMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N²,N^2'-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1'-biphenyl]-2,2'-dicarboxamide 在 盐酸 作用下， 反应 1.0h， 生成 N²,N^2'-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1'-biphenyl]-2,2'-dicarboxamide dihydrochloride
  参考文献：
  名称：

  Morphology dependant oxidation of aromatic alcohols by new symmetrical copper(II) metallatriangles formed by self-assembly of a shared bis-benzimidazolyl diamide ligand

  摘要：

  A new bis-benzimidazole-based diamide ligand N-2,N-2'-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1'-biphenyl]-2,2'-dicarboxamide, L and its three Cu(II) metallatriangles of general formula [Cu-3(L)(3)X-3]-center dot 3X center dot nH(2)O (where X = Cl, Br, NO3) have been synthesized and one of them is structurally characterized. X-ray diffraction work reveals that the metallatriangle [Cu-3(L)(3)Cl-3]center dot 3Cl center dot 15H(2)O crystallizes in trigonal R (3) over bar space group with two independent molecules in the asymmetric unit. The asymmetric unit contains only one-third of the molecules and the rest are generated by the crystallographic (3) over bar axis. Each copper(II) ion adopts a highly distorted square pyramidal geometry. The copper(II) metallatriangles are used as catalyst to carry out the oxidation of substituted benzyl alcohols heterogeneously, in the presence of tert-butyl hydroperoxide. Interestingly, the ratio of product profile and the percentage conversion of the products changes with the surface morphology of the metallatriangle employed as a catalyst. A kite type morphology is found to be highly selective to the formation of acid product over the aldehyde, while a hexagonal type morphology results in a mixed acid + aldehyde product. The initial rate of formation of the aldehyde is found to be almost independent of the amount of catalyst employed. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.12.037
• 作为产物：
  描述：

  2,2'-联苯二甲酸 、 2-(aminomethyl)benzimidazole dihydrochloride 在 吡啶 、 亚磷酸三苯酯 作用下， 生成 N²,N^2'-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1'-biphenyl]-2,2'-dicarboxamide
  参考文献：
  名称：

  使用通过配体共享形成的铜（II）金属三角形氧化取代的酚。

  摘要：

  N（2），N（2'）-双-[（（1-丁基-苯并咪唑-2基）甲基]联苯-2,2'-二甲酰胺（L）与CuX2·nH2O在甲醇中的反应导致组装成四个通式[Cu3（L）3X3]⋅3X⋅nH2O⋅mMeCN的三核Cu（II）配合物，其中X = Cl（-），Br（-），NO3（-）和C6H5COO（-），n = 0 -5，m = 0-8（分别为化合物1-4）。一种配合物的结构在等边三角形的角处包含三个Cu（II）金属离子。每个铜（II）通过两个苯并咪唑基亚胺亚胺N原子和两个酰胺羰基O原子配位，并且顶端位置被阴离子硝酸根离子占据，导致扭曲的方形锥体环境。通过哈密顿量H = -J（S1S2 + S2S3 + S1S3）分析磁化率数据，分别获得1-4的-J = 0.16、0.12、0.15和0.14cm（-1）。X波段EPR谱通常在120K处显示一条宽谱线，g值为2.11。以铜（II）金属三角形（1-3）为

  DOI：

  10.1016/j.saa.2014.06.026

文献信息

• Synthesis of a new N-substituted bis-benzimidazolyl diamide ligand and its trinuclear copper(II) complex: Structural and fluorescence studies
  作者：Kuldeep Mahiya、Pavan Mathur

  DOI：10.1016/j.saa.2013.05.006

  日期：2013.9

  The synthesis of a new N-substituted fluorescent probe based on a bis-benzimidazole diamide N(2),N(2')-bis[(1-(4-methylbenzyl)-benzimidazol-2-yl)methyl]biphenyl-2,2'-dicarboxamide (L1) with a biphenyl spacer group and its trinuclear copper(II) complex [Cu3(L1)3Cl3]·3Cl·3H2O] has been described. X-ray studies shows that the trinuclear complex crystallizes as [Cu3(L1)3Cl3}2·6Cl·13CH3CN·2H2O] in triclinic

  基于双苯并咪唑二酰胺N（2），N（2'）-双[（（1-（4-甲基苄基）-苯并咪唑-2-基）甲基]联苯-2的新型N取代荧光探针的合成已经描述了具有联苯间隔基的，2′-二甲酰胺（L1）及其三核铜（II）配合物[Cu3（L1）3Cl3]·3Cl·3H2O。X射线研究表明，三核配合物在三斜晶空间群P-1中结晶为[Cu3（L1）3Cl3} 2·6Cl·13CH3CN·2H2O]，在不对称单元中有两个独立的分子。每个铜（II）在每个单元中都采用扭曲的五坐标几何形状。L1在甲醇中的荧光光谱显示出以300 nm为中心的发射带。该带的产生是由于连接系统中的苯并咪唑基部分。Fe（3+）存在下的二酰胺L1显示（300nm）的“猝灭”和“增强” （375 nm）发射带。375 nm处的新发射带归因于联苯部分的内部配体π-π（*）跃迁。Cu（2+）和Ag（+）仅显示300 nm波段的猝灭。没有观察到其他金属离子，如Ni（2
• Bis-Benzimidazolyl Diamide Based Fluorescent Probe for Copper(II): Synthesis, Structural and Fluorescence Studies
  作者：Kuldeep Mahiya、Pavan Mathur

  DOI：10.1007/s10895-013-1182-1

  日期：2013.7

  A new fluorescent probe based on a bis-benzimidazole diamide N 2,N 2′-bis[(1-ethyl-benzimidazol-2-yl)methyl]biphenyl-2,2′-dicarboxamide ligand L 1 with a biphenyl spacer group and a Copper(II) trinuclear metallacycle has been synthesized and characterized by X-ray single crystallography, elemental and spectral (FT-IR, 1H & 13C NMR, UV-Visible) analysis. The fluorescence spectra of L 1 in MeOH show an emission band centered at 300 nm. This band arises due to benzimidazolyl moiety in the ligating system. The diamide L 1 in the presence of Cu2+ show the simultaneous ‘quenching’ of (300 nm) and ‘enhancement’ of (375 nm) emission band. Similar fluorescence behavior was found in water–methanol mixture (9:1). The new emission band at 375 nm is attributed to intra ligand π–π* transition of the biphenyl moiety. L 1 exhibited high selectivity and sensitivity towards Cu2+ in both the medium over other common metal ions like Ni2+, Co2+, Mn2+, Mg2+, Zn2+, Pb2+ and Hg2+. The binding constant with Cu2+ was calculated by the Benesi-Hildebrand equation. Selective “off-on-off” behavior of L 1 in methanol has also been studied. The fluorescent intensity of 375 nm bands in L 1 enhances (turns-on) upon addition of Cu2+ and quenches (turn-off) upon addition of Na2-EDTA.

  通过 X 射线单晶、元素和光谱（傅立叶变换红外光谱、1H &；13C NMR、紫外-可见光）分析。L 1 在 MeOH 中的荧光光谱显示出以 300 nm 为中心的发射带。该发射带是由连接系统中的苯并咪唑基引起的。在 Cu2+ 存在下，二酰胺 L 1 的发射带同时 "淬灭"（300 nm）和 "增强"（375 nm）。在水-甲醇混合物（9:1）中也发现了类似的荧光行为。375 nm 处的新发射带归因于联苯分子的配体内 π-π* 转变。在两种介质中，L 1 对 Cu2+ 都表现出较高的选择性和灵敏度，而对 Ni2+、Co2+、Mn2+、Mg2+、Zn2+、Pb2+ 和 Hg2+ 等其他常见金属离子的选择性和灵敏度则较低。与 Cu2+ 的结合常数是通过 Benesi-Hildebrand 公式计算得出的。还研究了 L 1 在甲醇中的选择性 "开关 "行为。加入 Cu2+ 时，L 1 中 375 nm 波段的荧光强度增强（开启）；加入 Na2-EDTA 时，荧光强度熄灭（关闭）。
• Morphology dependant oxidation of aromatic alcohols by new symmetrical copper(II) metallatriangles formed by self-assembly of a shared bis-benzimidazolyl diamide ligand
  作者：Kuldeep Mahiya、Pavan Mathur

  DOI：10.1016/j.ica.2012.12.037

  日期：2013.4

  A new bis-benzimidazole-based diamide ligand N-2,N-2'-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1'-biphenyl]-2,2'-dicarboxamide, L and its three Cu(II) metallatriangles of general formula [Cu-3(L)(3)X-3]-center dot 3X center dot nH(2)O (where X = Cl, Br, NO3) have been synthesized and one of them is structurally characterized. X-ray diffraction work reveals that the metallatriangle [Cu-3(L)(3)Cl-3]center dot 3Cl center dot 15H(2)O crystallizes in trigonal R (3) over bar space group with two independent molecules in the asymmetric unit. The asymmetric unit contains only one-third of the molecules and the rest are generated by the crystallographic (3) over bar axis. Each copper(II) ion adopts a highly distorted square pyramidal geometry. The copper(II) metallatriangles are used as catalyst to carry out the oxidation of substituted benzyl alcohols heterogeneously, in the presence of tert-butyl hydroperoxide. Interestingly, the ratio of product profile and the percentage conversion of the products changes with the surface morphology of the metallatriangle employed as a catalyst. A kite type morphology is found to be highly selective to the formation of acid product over the aldehyde, while a hexagonal type morphology results in a mixed acid + aldehyde product. The initial rate of formation of the aldehyde is found to be almost independent of the amount of catalyst employed. (C) 2013 Elsevier B.V. All rights reserved.
• Oxidation of substituted phenols using copper(II) metallatriangles formed through ligand sharing
  作者：Kuldeep Mahiya、Ravinder Kumar、Francisco Lloret、Pavan Mathur

  DOI：10.1016/j.saa.2014.06.026

  日期：2014.12

  line at 120K with g∼2.11. Oxidation of phenols was studied homogeneously using copper(II) metallatriangles (1-3) as catalyst in acetonitrile. The oxidation of 2,4,6-tri-tert-butyl phenol yields the corresponding quinone after oxidative dealkylation. The oxidation of 2-amino-5-methyl phenol yields the corresponding phenoxazinone while the oxidation of 2-amino-4-tert-butyl phenol yields the phenoxazine

  N（2），N（2'）-双-[（（1-丁基-苯并咪唑-2基）甲基]联苯-2,2'-二甲酰胺（L）与CuX2·nH2O在甲醇中的反应导致组装成四个通式[Cu3（L）3X3]⋅3X⋅nH2O⋅mMeCN的三核Cu（II）配合物，其中X = Cl（-），Br（-），NO3（-）和C6H5COO（-），n = 0 -5，m = 0-8（分别为化合物1-4）。一种配合物的结构在等边三角形的角处包含三个Cu（II）金属离子。每个铜（II）通过两个苯并咪唑基亚胺亚胺N原子和两个酰胺羰基O原子配位，并且顶端位置被阴离子硝酸根离子占据，导致扭曲的方形锥体环境。通过哈密顿量H = -J（S1S2 + S2S3 + S1S3）分析磁化率数据，分别获得1-4的-J = 0.16、0.12、0.15和0.14cm（-1）。X波段EPR谱通常在120K处显示一条宽谱线，g值为2.11。以铜（II）金属三角形（1-3）为