2-phenyl-6-(1H-pyrazol-3-yl)pyridine | 922164-00-9

• 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: 2-phenyl-6-(1H-pyrazol-3-yl)pyridine
• 英文别名: 2-Phenyl-6-(1H-pyrazol-5-yl)pyridine
• CAS: 922164-00-9
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: NGQAGKXOCBPMNP-UHFFFAOYSA-N

物化性质

• 沸点：
  445.6±30.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-6-(1H-pyrazol-3-yl)pyridine 以 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 生成 [Pt(2-phenyl-6-(1H-pyrazol-3-yl)pyridine)PPh3]ClO4*0.75H2O
  参考文献：
  名称：

  含有功能化环金属化配体2-苯基-6-（1H-吡唑-3-基）-吡啶的环金属化Pt（II）配合物的合成和光谱研究。

  摘要：

  三种新的发光环金属化Pt（II）配合物[Pt（L）Cl]（1），[Pt2（L-）2]（2）和[Pt（L）（PPh3）] ClO4（3.ClO4）（合成了其中HL ＝ 2-苯基-6-（1H-吡唑-3-基）-吡啶）并通过X-射线晶体学表征。HL代表一类新的C，N，Npyrazolyl环金属化配体，包含C苯基，Npyridyl和Npyrazolyl供体部分以及1-pyrazolyl-NH，也可用于金属配位和其他化学相互作用。配合物1在275-375 nm处具有强烈的配体内部跃迁，并在380-410 nm处具有中等强度的金属至配体电荷转移（1MLCT）（dpi（Pt）-> pi *（L））跃迁。室温固态发射lambdamax为1出现在580 nm处，可归因于3MMLCT（dsigma *（Pt）-> pi *（L））跃迁。它还在室温下在乙腈溶液中显示出强烈的磷光，发射λmax在514 nm，可以暂时分配给3MLCT（pi

  DOI：

  10.1021/ic062439j
• 作为产物：
  描述：

  2-乙酰基-6-苯基吡啶 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 2-phenyl-6-(1H-pyrazol-3-yl)pyridine
  参考文献：
  名称：

  A “Molecular Pivot-Hinge” Based on the pH-Regulated Intramolecular Switching of Pt−Pt and π−π Interactions

  摘要：

  The binuclear cycloplatinated complex {[Pt(L)]2(mu-dppm)}2+ (1), where HL is a new cyclometalating ligand 2-phenyl-6-(1H-pyrazol-3-yl)pyridine, is found to behave as a molecular pivot-hinge in which the closing and opening of the hinge is effected by the reversible formation and cleavage of the Pt-Pt d8-d8 interaction and the intramolecular pi-pi interaction mediated by the protonation/deprotonation of the 1-pyrazolyl-NH on the cyclometalating ligand L.

  DOI：

  10.1021/ja066914o

文献信息

• Porphyrin/Platinum(II) C^N^N Acetylide Complexes: Synthesis, Photophysical Properties, and Singlet Oxygen Generation
  作者：Atanu Jana、Luke McKenzie、Ashley B. Wragg、Masatoshi Ishida、Jonathan P. Hill、Julia A. Weinstein、Elizabeth Baggaley、Michael D. Ward

  DOI：10.1002/chem.201504509

  日期：2016.3.14

  solvents but, despite the PEG substituents, slowly aggregate in aqueous solvent systems. These conjugates also exhibit interesting photophysical properties, including near‐complete photoinduced energy transfer (PEnT) through the rigid acetylenic bond(s) from the PtII C^N^N antenna units to the ZnII porphyrin core, which shows sensitized luminescence, as shown by quenching of PtII C^N^N‐based luminescence

  已开发出一类新的取代卟啉，其中不同数量的环金属化的Pt II C ^ N ^ N乙炔化物和聚乙二醇（PEG）链连接到卟啉核心的内消旋位置，意在进行光物理，电化学，以及体外光诱导的单线态氧（1 O 2）生成研究。所有这些锌II卟啉-铂II C ^ N ^ N乙炔偶联物显示出中到高（Φ Δ＝ 0.55至0.63）单线态氧的产生效率。该络合物可溶于有机溶剂，但是尽管有PEG取代基，但在水性溶剂体系中却缓慢聚集。这些共轭物还表现出有趣的光物理性质，包括通过刚性炔键从Pt II C ^ N ^ N天线单元到Zn II卟啉核心的接近完全的光致能量转移（PEnT），表现出敏化的发光，如通过基于Pt II C ^ N ^ N的发光淬灭显示。电化学测量显示了一组氧化还原过程，这些过程大约是对Pt II C ^ N ^ N乙炔化物和Zn II所观察到的总和。卟啉单位。DFT计算支持UV / Vis光谱特性。
• A Triphenylphosphonium-Functionalised Cyclometalated Platinum(II) Complex as a Nucleolus-Specific Two-Photon Molecular Dye
  作者：Chi-Kin Koo、Leo K.-Y. So、Ka-Leung Wong、Yu-Man Ho、Yun-Wah Lam、Michael H.-W. Lam、Kwok-Wai Cheah、Chopen Chan-Wut Cheng、Wai-Ming Kwok

  DOI：10.1002/chem.200902919

  日期：2010.4.6

  [Pt(L3)Cl]+ can also produce two‐photon‐induced luminescence at room temperature upon excitation at 700 nm from a mode‐locked Ti:sapphire laser. Its two‐photon absorption cross‐section in DMF at room temperature was measured to be 28.0×10−50 cm4 s photon−1. [Pt(L3)Cl]+ is able to selectively stain the cell nucleolus. This has been demonstrated by two‐photon confocal imaging of live and methanol‐fixed

  有机金属环金属化铂（II）络合物[Pt（L 3）Cl] [PF 6 ]是由特殊设计的环金属配体HL 3（三苯基5- [3-（6-（6-苯基吡啶--2-基）-1 H-吡唑-1-基]戊基}氯化），它含有一个带有末端阳离子三苯基phosph部分的碳侧链。除了在溶液中具有室温下的单光子发光特性外，[Pt（L 3）Cl] +还可以通过锁模的Ti：蓝宝石激光器在700 nm的激发下在室温下产生双光子诱导的发光。在室温下，其在DMF中的双光子吸收截面测量为28.0×10 -50  cm4  s光子-1。[Pt（L 3）Cl] +能够选择性地染色细胞核仁。活和甲醇固定的HeLa（人类宫颈癌）和3T3（小鼠皮肤成纤维细胞）细胞的双光子共聚焦成像已证明了这一点。这种细胞器特异性可能与其对细胞核仁中蛋白质的特殊亲和力有关。由于这种蛋白质亲和力，[Pt（L 3）Cl] +是一种有效的RNA转录抑制剂，显示出相当深远的细胞毒性。另一方面，[Pt（L
• Pt(II)C^∧N^∧N-Based Luminophore−Micelle Adducts for Sensing Nitroaromatic Explosives
  作者：Prasenjit Maity、Aarti Bhatt、Bhavesh Agrawal、Atanu Jana

  DOI：10.1021/acs.langmuir.7b00869

  日期：2017.5.2

  becomes water-soluble in the presence of all kinds of surfactants, viz., cationic (e.g., cetyltrimethylammonium bromide, CTAB), anionic (e.g., sodium dodecyl sulfate, SDS), and neutral (e.g., Triton X-100). This may be due to the incorporation of its long lyophilic tail group (-C12H25) inside the micellar core, exposing planar Pt(II)C∧N∧N headgroup to the aqueous bulk phase. It was also observed that

  通过使用具有不同烷基取代基的不对称C∧N∧N配体，分别合成了两个发光的环金属化的Pt（II）配合物1•Pt和2•Pt。这些富含π电子的络合物用于感测各种缺乏电子的硝基芳族炸药，例如4-硝基甲苯（NT），2,4-二硝基甲苯（DNT），2,4,6-三硝基甲苯（TNT）和2,4 ，6-三硝基苯酚（TNP），水性，非水性以及固态的纸条，最大检出限为。10-9M。证明了在各种表面活性剂的存在下微溶的2•Pt络合物变成水溶性，这些表面活性剂包括阳离子表面活性剂（例如十六烷基三甲基溴化铵CTAB），阴离子表面活性剂（例如十二烷基硫酸钠， SDS）和中性（例如Triton X-100）。这可能是由于其长的亲液性尾基（-C12H25）掺入了胶束核心，使平面的Pt（II）C∧N= N头基暴露于水相。还观察到这些Pt（II）配合物在胶束介质中的溶解度在很大程度上取决于现有烷基链的长度。例如，更长的十二烷基链的存
• Preparation of Phosphorescent Osmium(IV) Complexes with N,N′,C- and C,N,C′-Pincer Ligands
  作者：Roberto G. Alabau、Miguel A. Esteruelas、Montserrat Oliván、Enrique Oñate

  DOI：10.1021/acs.organomet.7b00193

  日期：2017.5.8

  Four different pincer ligands, which prove that the disposition of the donor atoms in pincer ligands allows them to develop a marked ability to form less common coordination polyhedra and to favor unusual metal oxidation states, have been generated starting from OsH6((PPr3)-Pr-i)(2) and 2-phenyl-6-(1H-pyrazol-3-yl)pyridine (Hpz-py-Ph) in order to stabilize 1 phosphorescent, pentagonal-bipyramidal osmium(IV) emitters. Complex 1 reacts with the disubstituted heterocycle to give OsH2kappa(3)-N,N',C-(pz-py-C6H4)}((PPr3)-Pr-i)(2) (2), as a result of the activation of a phenyl o-CH bond and the pyrazolyl N-H of the pyridine substituents. The addition of methyl trifluoromethanesulfonate (MeOTf) to 2 produces the methylation of the free N atom of the pz group and the formation of the salt [OsH2kappa(3)-N,N',C-(Mepz-py-C6H4)}((PPr3)-Pr-i)(2)]OTf (3), which undergoes deprotonation of the metal center in the presence of (KOBu)-Bu-t. The resulting monohydride OsHkappa(3)-N,N',C-(Mepz-py-C6H4)}((PPr3)-Pr-i)(2) (4) is unstable and evolves into OsH2kappa(3)-C,N,C'-(Mepz-py-C6H4)}((PPr3)-Pr-i)(2) (5) as a consequence of the oxidative addition of the C-H bond at position 4 of the Mepz group to the osmium atom of 4. The addition of MeOTf to 5 produces the methylation of the free N atom of the Mepz group, which is converted into a remote N-heterocyclic carbene, to form [OsH2kappa(3)-C,N,C'-(Me(2)pz-py-C6H4)}((PPr3)-Pr-i)OTf (6). Complex 1 also reacts with 2-(1H-pyrazol-3-yl)pyridine(Hpz-py). The reaction gives rise to the trihydride derivative OsH3kappa(2)-N,N-(pz-py)}((PPr3)-Pr-i)(2) (7), which leads to the salt [OsH3kappa(2)-N,N-(Mepz-py)}((PPr3)-Pr-i)(2)]OTf (8) by addition of MeOTf. The deprotonation of 8 affords the osmium(II) dihydride OsH2kappa(2)-N,N-(Mepz-py)}((PPr3)-Pr-i)(2) (9), which is stable, in contrast to 4. Complexes 2, 3, 5, 7, and 8 are emissive in the green to red region upon photoexcitation.
• IRIDIUM COMPLEXES AND ORGANIC LIGHT-EMITTING DIODES USING THE SAME
  申请人：National Tsing Hua University

  公开号：US20160359129A1

  公开（公告）日：2016-12-08

  An iridium complex represented by formula (1) and an OLED using the same are shown. In Formula (1), l, m, n, p, b, R 1 -R 6 , X 1 -X 6 , A 1 , A 2 and B are the same as defined in the specification. The iridium complex is able to emit a range of visible light with high color purity and high efficiency as neat sample.