4'-(3'''-aminophenyl)-2,2':6,2''-terpyridine | 158014-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4'-(3'''-aminophenyl)-2,2':6,2''-terpyridine
• 英文别名: 3-aminophenylterpyridine；3-(2,6-Dipyridin-2-ylpyridin-4-yl)aniline
• CAS: 158014-73-4
• 化学式: C₂₁H₁₆N₄
• 分子量: 324.385
• InChiKey: KGOXEWWDRKUUKP-UHFFFAOYSA-N

物化性质

• 沸点：
  537.7±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6,7,12-四叔丁基苯氧基苝-3,4,9,10-四甲酸二酐 、 4'-(3'''-aminophenyl)-2,2':6,2''-terpyridine 在 喹啉 作用下， 反应 72.0h， 以60%的产率得到N,N'-bis[3-([2,2':6',2"]terpyridin-4'-yl)phenyl]-1,6,7,12-tetra(p-t-butylphenol)perylene-3,4:9,10-tetracarboxylic acid bisanhydride
  参考文献：
  名称：

  Perylene-Based, Bis(terpyridine)-Ru(II) Complexes: Synthesis, Electrochemical and Photovoltaic Properties

  摘要：

  Perylene-based, terpyridine-Ru(II) complexes are synthesized and their electrochemical and photoelectrochemical properties are studied; their fabrication into dye-sensitized solar cells are described (DSSCs) and their resultant photovoltaic properties are evaluated.

  DOI：

  10.3987/com-14-s(k)49
• 作为产物：
  描述：

  4-(3-硝基苯基)-2,6-二吡啶-2-基吡啶 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 4'-(3'''-aminophenyl)-2,2':6,2''-terpyridine
  参考文献：
  名称：

  一个非常稳定的氢键结合的卟啉·铁（吡啶）离子对。

  摘要：

  即使在竞争激烈的溶剂（例如DMSO）中，卟啉双（羧酸根）二价阴离子与铁（三吡啶）双（脲）之间的氢键键合和离子配对也可导致强烈的双分子缔合和随后的荧光猝灭。

  DOI：

  10.1039/b106430b

文献信息

• The synthesis of 4′-aryl substituted terpyridines by Suzuki cross-coupling reactions: substituent effects on ligand fluorescence
  作者：Wendy Goodall、Kerstin Wild、Kathryn J. Arm、J. A. Gareth Williams

  DOI：10.1039/b205330f

  日期：——

  Several 4′-aryl-substituted 2,2′:6′,2″-terpyridines (tpy-C6H4R) have been prepared by palladium-catalysed cross-coupling of 4′-bromoterpyridine or 4′-triflate-terpyridine (triflate = trifluoromethylsulfonyloxy) with aryl boronic acids or esters, RC6H4B(OR′)2 (R = H, m-NH2, p-CHO, -NO2, -CN, -NMe2, -NPh2). The new ligand 4′-mesitylterpyridine (mesityl = 2,4,6-trimethylphenyl) was prepared in the same way. Similarly, 4′-bromophenylterpyridine (tpy-ϕ-Br) has been cross-coupled with aryl halides to generate several new biaryl-substituted terpyridines (tpy-ϕ-C6H4R where R = H, p-CN, NMe2, NPh2), together with two related compounds with pendent 3- or 4-pyridyl groups (tpy-ϕ-C6H4-py). For selected compounds, the alternative coupling strategy of reaction of a terpyridine-4-boronate or terpyridine-4-phenylboronate with the appropriate aryl halide has also been investigated (e.g. to prepare tpy-ϕ-C6H4NO2), but was generally found to be less satisfactory. All of the compounds are fluorescent in the UV region of the spectrum, the biaryl-substituted compounds being only slightly red-shifted compared to the monoaryl systems, but with the further red-shift that accompanies protonation being more significant for the former. Fluorescence lifetimes in solution are in the range 1–5 ns. The emission spectra of the aminobiphenyl-substituted compounds (tpy-ϕ-C6H4NR″2, where R″ = Me or Ph) display a large red-shift with increasing solvent polarity, suggesting the involvement of an intramolecular charge transfer state, as found previously for the two analogues omitting the phenyl ring (tpy-C6H4NR″2). In contrast to the latter, however, protonation or binding of a Lewis acidic metal ion to the aminobiphenyl compounds serves to quench almost completely their emission.

  通过钯催化的交叉偶联反应，制备了几种4′-芳基取代的2,2′:6′,2″-三联吡啶（tpy-C6H4R），涉及4′-溴三联吡啶或4′-三氟甲磺酸酯三联吡啶（triflate = 三氟甲磺酰氧基）与芳基硼酸或硼酸酯的反应，RC6H4B(OR′)2（R = H, m-NH2, p-CHO, -NO2, -CN, -NMe2, -NPh2）。新配体4′-三甲基苯基三联吡啶（mesityl = 2,4,6-三甲基苯基）也通过相同方法制备。类似地，4′-溴苯基三联吡啶（tpy-Φ-Br）已与芳基卤化物交叉偶联，生成了几种新的双芳基取代三联吡啶（tpy-Φ-C6H4R，其中R = H, p-CN, NMe2, NPh2），以及两种含有3-或4-吡啶基侧链的相关化合物（tpy-Φ-C6H4-py）。对于选定的化合物，还研究了替代的偶联策略，即反应一个三联吡啶-4-硼酸酯或三联吡啶-4-苯基硼酸酯与适当的芳基卤化物（例如制备tpy-Φ-C6H4NO2），但通常发现效果较差。所有化合物在紫外区域都有荧光发射，双芳基取代的化合物相比于单芳基系统仅有轻微的红移，但其伴随质子化产生的进一步红移对前者更为显著。溶液中的荧光寿命在1~5纳秒范围内。氨基联苯取代化合物的发射光谱（tpy-Φ-C6H4NR″2，其中R″ = Me或Ph）随着溶剂极性的增加显示出较大的红移，表明存在分子内电荷转移态，这与先前报道的两种省略苯环的类似物（tpy-C6H4NR″2）一致。然而，与后者不同，氨基联苯化合物在质子化或与路易斯酸性金属离子结合时，其发射几乎完全淬灭。
• A remarkably stable hydrogen-bonded porphyrin·iron(terpyridine) ion pair
  作者：Tyler B. Norsten、Kelly Chichak、Neil R. Branda

  DOI：10.1039/b106430b

  日期：——

  Even in highly competitive solvents such as DMSO, strong bimolecular association and subsequent fluorescence quenching result from the combination of hydrogen bonding and ion pairing between a porphyrinic bis(carboxylate) dianion and an iron(terpyridine) bis(urea).

  即使在竞争激烈的溶剂（例如DMSO）中，卟啉双（羧酸根）二价阴离子与铁（三吡啶）双（脲）之间的氢键键合和离子配对也可导致强烈的双分子缔合和随后的荧光猝灭。
• PHARMACEUTICAL USE OF TERPYRIDINE DERIVATIVE
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0677293A1

  公开（公告）日：1995-10-18

  A terpyridine derivative represented by general formula (I) (wherein R represents hydrogen, (un)substituted phenyl, pyridyl, etc.), which has the effect of promoting the production of nerve growth factors or a neurotrophic factor activity. Hence it can be used as an ameliorant or remedy for the symptoms and diseases accompanying peripheral nerve degeneration which is idiopathic or caused by trauma, chemicals such as alcohol or anticancer drug, inflammation, or metabolism as observed in, for example, diabetes. In addition, it can be used as an ameliorant or remedy for the symptoms and diseases accompanying central nerve degeneration, such as senile dementia of Alzheimer type, cerebrovascular dementia, Down's syndrome, Parkinson's disease or Hantington's chorea, mental and motor function incompetences caused by cerebral ischemia, cerebral infarction, cerebral hemorrhage or head injury, spinal neuroparalysis, and so forth.

  一种由通式(I)代表的terpyridine衍生物（其中R代表氢、（未）取代的苯基、吡啶基等），具有促进神经生长因子或神经营养因子活性产生的作用。因此，它可作为一种改善剂或治疗剂，用于治疗特发性或由创伤、化学物质（如酒精或抗癌药物）、炎症或代谢（如糖尿病）引起的伴随周围神经变性的症状和疾病。此外，它还可用于改善或治疗中枢神经退化引起的症状和疾病，如阿尔茨海默型老年痴呆、脑血管性痴呆、唐氏综合征、帕金森病或汉廷顿舞蹈症、脑缺血、脑梗塞、脑出血或头部损伤引起的精神和运动功能障碍、脊髓神经麻痹等。
• Strong and directed association of porphyrins and iron(terpyridine)s using hydrogen bonding and ion pairing
  作者：Tyler B Norsten、Kelly Chichak、Neil R Branda

  DOI：10.1016/s0040-4020(01)01096-1

  日期：2002.1

  The combination of cooperative hydrogen bonding and ion pairing between cationic iron(II)terpyfidines and anionic porphyrins yielded remarkably stable neutral complexes even in the highly competitive solvent DMSO. Isothermal titration calorimetry (ITC) was used to compare association constants, enthalpies and entropies of binding between various combinations of the two molecular components that make up the complexes. Steady-state luminescence studies highlighted that, as expected, the fluorescence quenching of the porphyrin is maximized in the cases where the iron(terpyridine) is strapped the tightest across the macrocycle. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Perylene-Based, Bis(terpyridine)-Ru(II) Complexes: Synthesis, Electrochemical and Photovoltaic Properties
  作者：George R. Newkome、Hany El-Batal、Juan Manríquez Rocha、Luis A. Godínez、Kai Guo、Xiaopeng Li、Xiaocun Lu、Chrys Wesdemiotis、Charles N. Moorefield、Perla F. Méndez

  DOI：10.3987/com-14-s(k)49

  日期：——

  Perylene-based, terpyridine-Ru(II) complexes are synthesized and their electrochemical and photoelectrochemical properties are studied; their fabrication into dye-sensitized solar cells are described (DSSCs) and their resultant photovoltaic properties are evaluated.