N,N-bis(3-methoxysalicylidene)-1,4-diaminobutane | 104978-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N-bis(3-methoxysalicylidene)-1,4-diaminobutane
• 英文别名: O-Cresol, alpha,alpha'-(tetramethylenedinitrilo)bis[6-methoxy-；2-[4-[(2-hydroxy-3-methoxyphenyl)methylideneamino]butyliminomethyl]-6-methoxyphenol
• CAS: 104978-24-7
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: PSJZCPKYFYKXHM-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  536.6±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cobalt(II) chloride hexahydrate 、 N,N-bis(3-methoxysalicylidene)-1,4-diaminobutane 以 sodium hydroxide 为溶剂， 生成 bis(2-hydroxy-3-methoxy-benzylidene)-tetramethylene-diamine-cobalt(II)
  参考文献：
  名称：

  Diehl, H.; Liggett, L. M.; Hach, C. C., Iowa State College Journal of Science, 1947, vol. 22, p. 110 - 125

  摘要：

  DOI：
• 作为产物：
  描述：

  邻香草醛 、 四亚甲基二胺 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到N,N-bis(3-methoxysalicylidene)-1,4-diaminobutane
  参考文献：
  名称：

  硝酸盐抗衡离子组装的Mn（III）-席夫碱配合物的超分子网络：一维链和二维网络的X射线晶体结构

  摘要：

  摘要从3-甲氧基-2-羟基苯甲醛与不同的二胺缩合得到的双阴离子六齿席夫碱合成了一系列硝酸锰（III）配合物。通过元素分析，ESI质谱，IR和1H NMR光谱对复合物进行了表征。还进行了磁研究和摩尔电导率测量。配合物[MnL1（H2O）2] 2·2NO3·2CH3OH（1），[MnL2（H2O）2] 2·2NO3·2CH3OH（2）和[MnL5（H2O）2] 2·2NO3·6H2O（5）结晶表征。X射线结构显示出金属周围的八面体几何形状，赤道面上的席夫碱作为四齿，轴向上的水或甲醇分子起作用。八面体实体通过相邻轴向水分子之间的a-aquo桥成对连接，也通过π-π堆积相互作用成对连接，建立二聚体和聚合物结构。硝酸根阴离子被容纳在骨架的空腔中，并与水配体和甲醇或结晶水形成氢键，导致络合物的无限超分子聚集。氯离子，高氯酸根和硝酸根络合物的比较表明，阴离子的性质是指导结构拓扑的关键因素。

  DOI：

  10.1016/j.poly.2011.09.031

文献信息

• The Crystal Structures of [N,N’-Bis(3-methoxysalicylidene)-1,3- diaminopropane]nickel(II) and -copper(II)
  作者：Ayhan Elmali、Celal T Zeyrek、Yalcin Elerman

  DOI：10.1515/znb-2004-0216

  日期：2004.2.1

  [N,N′’-Bis(3-methoxysalicylidene)-1,3-diaminopropane]nickel(II) dihydrate [Ni(C₁₉H₂₀N₂O₄)· 2(H₂O)] 1 and [N,N′-bis(3-methoxysalicylidene)-1,4-diaminobutane]copper(II) [Cu(C₂₀H₂₂N₂O₄)] 2 have been synthesized and their crystal structures determined. Crystals of compound 1 are orthorhombic, space group Pnma, a = 7.509(3), b = 22.070(7), c = 11.532(4) Å, V = 1611.1(12) ų, Z = 4 and D_c = 1.498 g·cm⁻³. The molecule 1 has mirror symmetry, but the ligand is not planar. The two parts of the Schiff base moieties are folded so as to form an angle of 21.6(1)°. The Ni atom is in a distorted octahedral geometry and coordinated by the donor atoms of the ligand in the horizontal plane and of two water molecules. Crystals of compound 2 are monoclinic, space group P2₁/c, a = 9.488(1), b = 21.918(3), c = 8.413(1) Å, β = 91.45(1)°, V = 1749.0(4) ų, Z = 4 and D_c = 1.587 g·cm⁻³. The Cu atom is coordinated by an N₂O₂ donor set from the imine-phenol ligand in a distorted planar geometry, with the two phenolate O atoms deprotonated. The Cu-O bond lengths are 1.854(3) and 1.868(3)Å . The Cu-N bond lengths are 1.931(3) and 1.950(3) Å, the dihedral angle between the two 3-methoxysalicylidene groups is 43.4(1)°.

  [N,N′’-双(3-甲氧基水杨醛亚胺)-1,3-二氨基丙烷]二水合物镍(II) [Ni(C₁₉H₂₀N₂O₄)· 2(H₂O)] 1 和[N,N′-双(3-甲氧基水杨醛亚胺)-1,4-二氨基丁烷]铜(II) [Cu(C₂₀H₂₂N₂O₄)] 2 已合成并确定了它们的晶体结构。化合物1的晶体为正交晶系，空间群Pnma，a = 7.509(3) Å，b = 22.070(7) Å，c = 11.532(4) Å，V = 1611.1(12) ų，Z = 4，D_c = 1.498 g·cm⁻³。分子1具有镜像对称性，但配体不是平面的。Schiff碱基的两部分折叠形成21.6(1)°的角度。镍原子处于扭曲的八面体几何构型，并由水平面的配体供体原子和两个水分子配位。化合物2的晶体为单斜晶系，空间群P2₁/c，a = 9.488(1) Å，b = 21.918(3) Å，c = 8.413(1) Å，β = 91.45(1)°，V = 1749.0(4) ų，Z = 4，D_c = 1.587 g·cm⁻³。铜原子由偏平面几何构型中的亚胺-酚配体的N₂O₂供体集合配位，两个酚氧原子被去质子化。Cu-O 键长为1.854(3) Å和1.868(3) Å。Cu-N 键长为1.931(3) Å和1.950(3) Å，两个3-甲氧基水杨醛亚胺基团之间的二面角为43.4(1)°。
• Syntheses, crystal structures, and solid-state photoluminescence properties of heterotrinuclear Zn2Ln (Ln: La, Sm, Eu, Tb) complexes derived from 1,4-diaminobutane-based N2O4 compartmental ligand
  作者：Daishin Kori、Yuma Dote、Masayuki Koikawa、Yasunori Yamada

  DOI：10.1016/j.poly.2019.06.012

  日期：2019.9

  shows a reddish-orange colored f–f photoluminescence via an energy transfer from the T1 state localized on the Zn(MeOsalbn)} units to the acceptor level of the central Sm(III) ion. The results of TD-DFT calculations show that the lowest excited singlet state or triplet state involved in photoluminescence of the La(III) or Sm(III) complex has some intramolecular charge-transfer (CT) character from the

  摘要N，N'-双（3-甲氧基水杨基亚基）-1,4-二氨基丁烷（MeOsalbnH2），高氯酸锌（II）和乙酸镧系元素（III）的摩尔比为2：2：1的一锅反应可以得到配制成[Ln（CH3COO）2 Zn（MeOsalbn）} 2] ClO4的杂三核Zn2Ln（Ln：La，Sm，Eu，Tb）络合物。在该络合物中，中心的Ln（III）原子被两个Zn（MeOsalbn）}单元和两个乙酸酯配体桥接，形成十配位环境。每个Zn（II）原子都通过MeOsalbn2-通过N2O2位点与一个氧原子从桥连乙酸盐中进行配位，以提供五配位几何形状。在室温下的结晶状态下，La（III）配合物显示出明亮的蓝色荧光，而Sm（III）络合物通过能量转移从位于Zn（MeOsalbn）}单元上的T1态到中心Sm（III）离子的受主能级显示出橙红色的f-f光致发光。TD-DFT计算结果表明，参与La（III）或Sm（III
• Anion-dependent construction of two hexanuclear 3d–4f complexes with a flexible Schiff base ligand
  作者：Xiaoping Yang、Christopher Chan、Daniel Lam、Desmond Schipper、Julie M. Stanley、Xiaoyan Chen、Richard A. Jones、Bradley J. Holliday、Wai-Kwok Wong、Shengchun Chen、Qun Chen

  DOI：10.1039/c2dt31268a

  日期：——

  Two hexanuclear 3d–4f Ni–Eu and Cu–Eu complexes [Eu4Ni2L2(OAc)12(EtOH)2] (1) and [Eu4Cu2L2(OAc)12]·2H2O (2) are reported which are formed from the salen type Schiff-base ligand H2L (H2L = N,N′-bis(3-methoxysalicylidene)butane-1,4-diamine). In both complexes, four Eu3+ cations are bridged by eight OAc− groups and the chain is terminated at each end by two ML (M = Ni and Cu) units. The structures of 1 and 2 were determined by single crystal X-ray crystallographic studies and the luminescence properties of the free ligand and metal complexes in solution were measured.

  本报告介绍了两种六核 3dâ4f NiâEu 和 CuâEu 复合物 [Eu4Ni2L2(OAc)12(EtOH)2] (1) 和 [Eu4Cu2L2(OAc)12]Â-2H2O (2)，它们是由 Salen 型希夫碱配体 H2L（H2L = N,Nâ²-双(3-甲氧基水杨酰)丁烷-1,4-二胺）形成的。在这两种配合物中，四个 Eu3+ 阳离子由八个 OAcâ 基团桥接，链的两端分别以两个 ML（M = Ni 和 Cu）单元终止。通过单晶 X 射线晶体学研究确定了 1 和 2 的结构，并测量了游离配体和金属配合物在溶液中的发光特性。
• Ligand influence <i>versus</i> electronic configuration of d-metal ion in determining the fate of NIR emission from Ln^III ions: a case study with Cu^II, Ni^II and Zn^II complexes
  作者：Abhineet Verma、S. K. Saddam Hossain、Sailaja S. Sunkari、Joseph Reibenspies、Satyen Saha

  DOI：10.1039/d0nj04020g

  日期：——

  Based on fifteen lanthanide complexes, where Cu, Ni and Zn ions with a Schiff-base ligand act as an antenna, it is demonstrated that electronic configuration of the d-block metal ion is very crucial for obtaining emission in NIR region.

  基于十五个镧系金属配合物，其中铜、镍和锌离子与席夫碱配体作为天线，证明了d-块金属离子的电子构型对于获得近红外区域的发射非常关键。
• Construction of 1-D 4f and 3d–4f coordination polymers with flexible Schiff base ligands
  作者：Xiaoping Yang、Daniel Lam、Christopher Chan、Julie M. Stanley、Richard A. Jones、Bradley J. Holliday、Wai-Kwok Wong

  DOI：10.1039/c1dt11036e

  日期：——

  Three new lanthanide 1-D coordination polymers ([Ln2(H2L)(OAc)6]·EtOH·2H2O}n (Ln = Eu (1), Er (2)) and YbNiLCl(OAc)2(H2O)}n (3)) and a heterobinuclear complex [YbNiLCl3(H2O)3] (4) are reported which are formed from salen type Schiff-base ligands H2L (H2L = N,N′-bis(3-methoxysalicylidene)butane-1,4-diamine). The polymeric structures are formed by bridging H2L units in the case of 1 and 2, and by acetate groups in 3. The structures of 1–4 were determined by single crystal X-ray crystallographic studies and their luminescence properties in MeCN solution were determined.

  三种新型镧系元素一维配位聚合物 ([Ln2(H2L)(OAc)6]·EtOH·2 }n (Ln = Eu (1), Er (2)) 和 YbNiLCl(OAc)2(H2O) }n (3)) 和异双核配合物 [YbNiLCl3( )3] (4) 被报道是由 salen 型希夫碱配体 H2L (H2L = N,N-bis(3-methoxysalicylidene)butane- 1,4-二胺）。 1和2中的聚合结构是通过桥接H2L单元形成的，3中是通过乙酸基团形成的。1-4的结构通过单晶X射线晶体学研究确定，并测定了它们在MeCN溶液中的发光性质。