4-(2,2':6',2''-terpyridinyl-4'-yl)-benzyltriphenylphosphonium bromide

• 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: 4-(2,2':6',2''-terpyridinyl-4'-yl)-benzyltriphenylphosphonium bromide
• 英文别名: 4′-p-triphenylphosphinemethylphenyl-2,2′:6,2″-terpyridine bromide；4-(2,2':6',2''-terpyridyl-4')-benzyl triphenylphosphoniumbromide；Bromo-[[4-(2,6-dipyridin-2-ylpyridin-4-yl)phenyl]methyl]-triphenyl-lambda5-phosphane；bromo-[[4-(2,6-dipyridin-2-ylpyridin-4-yl)phenyl]methyl]-triphenyl-λ5-phosphane
• 化学式: C₄₀H₃₁BrN₃P
• 分子量: 664.584
• InChiKey: MFBRDIIXNDNXLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,2':6',2''-terpyridinyl-4'-yl)-benzyltriphenylphosphonium bromide 、 4-(1-1,2,4-三唑基)苯甲醛 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以76%的产率得到4’-(4-[4-(1H-[1,2,4]-triazolyl)styryl]phenyl)-2,2’:6’,2''-terpyridine
  参考文献：
  名称：

  A new 2,2′:6′,2′′-terpyridine-based ligand and its complexes: structures, photophysical properties and DFT calculations to evaluate the halogen effect on the TPA

  摘要：

  我们合成了一种新型 2,2':6',2â²â²-三吡啶配体（L）和八种配合物，并对其进行了全面表征。通过单晶 X 射线衍射分析确定了其中六个配合物（[CdLBr2]2Â-CHCl3 (2)、ZnLI2 (3)、[CdLI2]2Â-CH2Cl2 (4)、ZnL(SCN)2Â-CHCl3 (5)、[ZnL2]2(ClO4)4Â-7H2O (7) 和 [CdL2](ClO4)2Â-CH3OH (8)）。各种弱相互作用，包括氢键（CâHâ¯N、CâHâ¯X）、CâHâ¯和ÏâÏ相互作用在最终的超分子结构中发挥了重要作用。本文描述了配体和八种配合物的线性和非线性光学特性。实验结果表明，这些配合物的双光子吸收（TPA）截面比配体的大得多，在 DMF 中，L 和配合物 1â8 的最大值分别为 97、661、787、218、133、613、230、384 和 241 GM。对 1â6 进行的密度泛函理论（DFT）计算表明，由于电子感应效应不同，卤素会影响周围金属的接受能力，其顺序为 Br > SCN > I。结果表明，TPA 横截面的变化顺序为 Br > SCN > I，这与实验结果一致。

  DOI：

  10.1039/c2ce25467k
• 作为产物：
  描述：

  2-乙酰基吡啶 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium hydroxide 作用下， 以 四氯化碳 、 乙醇 、 甲苯 为溶剂， 反应 44.0h， 生成 4-(2,2':6',2''-terpyridinyl-4'-yl)-benzyltriphenylphosphonium bromide
  参考文献：
  名称：

  Arylene–vinylene terpyridine conjugates: highly sensitive, reusable and simple fluorescent probes for the detection of nitroaromatics

  摘要：

  一系列高发射率的芳烃-乙烯基三吡啶共轭物已经被开发用于检测硝基芳香化合物（NAC）炸药，作为高效可重复使用的荧光探针。

  DOI：

  10.1039/c7tc04178k

文献信息

• Synthesis, characterization, emission and DNA binding properties of four alkynylplatinum(II) terpyridine complexes
  作者：Pengfei Shi、Qin Jiang、Qiong Zhang、Yupeng Tian

  DOI：10.1016/j.jorganchem.2015.12.017

  日期：2016.2

  Four novel alkynylplatinum(II) terpyridine complexes, [Pt(C CPhR)L]Cl (L = (E)-'0-(4-N, N-bis(2-(2-methoxyethoxy) ethylamino) styrylphenyl)-2,2': 6',2 ''-terpyridine (O4TPY) or 4'-p-N, N-bis(2-hydroxyethyl) aminobenzyl-2,2': 6',2 ''-terpyridine (TPYOH) and R = n-Bu or H), were synthesized and characterized using H-1 NMR, C-13 NMR, MALDI-TOF-MS and elemental analysis. All Pt(II) complexes were weakly emissive at ambient temperature in a mixed solution of acetonitrile and water, in which two alkynylplatinum(II) complexes of TPYOH showed much longer emission maximum than those of O4TPY (677 nm for [Pt(C CPh) (TPYOH)] Cl vs 581 nm for [Pt(C CPh) (O4TPY)] Cl and 689 nm for [Pt(C CPhBu) (TPYOH)] Cl vs 595 nm for [Pt(C CPhBu) (O4TPY)] Cl). UV-vistitration experiments indicated that only two alkynylplatinum(II) complexes of O4TPY can bind CT-DNA and the binding constant K-b was 1.9 x 10(5) for [Pt(C CPh) (O4TPY)] Cl and 1.1 x 105 for [Pt(C CPhBu) (O4TPY)] Cl, respectively. The circular dichroism results indicted that the complexes [Pt(C CPhR) (O4TPY)] Cl can change the helicity of DNA, while the complexes [Pt(C CPhR) (TPYOH)] Cl could interact with the DNA base pair. The influence of ligands in the four complexes on their emission and DNA binding properties were discussed. (C) 2015 Elsevier B.V. All rights reserved.
• A new 2,2′:6′,2′′-terpyridine-based ligand and its complexes: structures, photophysical properties and DFT calculations to evaluate the halogen effect on the TPA
  作者：Fei-Xia Zhou、Zheng Zheng、Hong-Ping Zhou、Wei-Zai Ke、Jian-Qing Wang、Zhi-Peng Yu、Feng Jin、Jia-Xiang Yang、Jie-Ying Wu、Yu-Peng Tian

  DOI：10.1039/c2ce25467k

  日期：——

  A novel 2,2':6',2′′-terpyridine-based ligand (L) and eight complexes have been synthesized and fully characterized. Six of these complexes ([CdLBr2]2·CHCl3 (2), ZnLI2 (3), [CdLI2]2·CH2Cl2 (4), ZnL(SCN)2·CHCl3 (5), [ZnL2]2(ClO4)4·7H2O (7) and [CdL2](ClO4)2·CH3OH (8)) were determined by single crystal X-ray diffraction analysis. Various weak interactions, including hydrogen bonds (C–H⋯N, C–H⋯X), C–H⋯π and π–π interactions played significant roles in the final supramolecular structures. Linear and nonlinear optical properties of the ligand and eight complexes are described. Experimental results reveal that two-photon absorption (TPA) cross-sections of these complexes are extraordinarily larger than that of the ligand, with maximum values of 97, 661, 787, 218, 133, 613, 230, 384 and 241 GM for L and complexes 1–8 in DMF, respectively. Density functional theory (DFT) calculations were performed on 1–6 and revealed that the halogen affects the accepting capability of surrounding metals due to different electron inductive effects, in the order Br > SCN > I. Thus, this in turn affects the TPA cross-section values. The results indicate that the TPA cross-sections vary in the order Br > SCN > I, which is consistent with the experimental results.

  我们合成了一种新型 2,2':6',2â²â²-三吡啶配体（L）和八种配合物，并对其进行了全面表征。通过单晶 X 射线衍射分析确定了其中六个配合物（[CdLBr2]2Â-CHCl3 (2)、ZnLI2 (3)、[CdLI2]2Â-CH2Cl2 (4)、ZnL(SCN)2Â-CHCl3 (5)、[ZnL2]2(ClO4)4Â-7H2O (7) 和 [CdL2](ClO4)2Â-CH3OH (8)）。各种弱相互作用，包括氢键（CâHâ¯N、CâHâ¯X）、CâHâ¯和ÏâÏ相互作用在最终的超分子结构中发挥了重要作用。本文描述了配体和八种配合物的线性和非线性光学特性。实验结果表明，这些配合物的双光子吸收（TPA）截面比配体的大得多，在 DMF 中，L 和配合物 1â8 的最大值分别为 97、661、787、218、133、613、230、384 和 241 GM。对 1â6 进行的密度泛函理论（DFT）计算表明，由于电子感应效应不同，卤素会影响周围金属的接受能力，其顺序为 Br > SCN > I。结果表明，TPA 横截面的变化顺序为 Br > SCN > I，这与实验结果一致。
• Arylene–vinylene terpyridine conjugates: highly sensitive, reusable and simple fluorescent probes for the detection of nitroaromatics
  作者：Amit Sil、Dipanjan Giri、Sanjib K. Patra

  DOI：10.1039/c7tc04178k

  日期：——

  A series of highly emissive arylene–vinylene terpyridine conjugates have been developed for the detection of nitroaromatic (NAC) explosives as efficient and reusable fluorescent probes.

  一系列高发射率的芳烃-乙烯基三吡啶共轭物已经被开发用于检测硝基芳香化合物（NAC）炸药，作为高效可重复使用的荧光探针。