4-(3-hydroxy-3-methyl-1-butynyl)phthalonitrile | 193270-07-4

• 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-(3-hydroxy-3-methyl-1-butynyl)phthalonitrile
• 英文别名: 4-(3-Hydroxy-3-methylbut-1-yn-1-yl)benzene-1,2-dicarbonitrile；4-(3-hydroxy-3-methylbut-1-ynyl)benzene-1,2-dicarbonitrile
• CAS: 193270-07-4
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: JYPVCEFYCVNNJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxy-3-methyl-1-butynyl)phthalonitrile 在 sodium hydroxide 、 无水二甲氨基乙醇 、 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 23-ethynyl-2,3,9,10,16,17-hexabutoxyphthalocyaninatozinc(II)
  参考文献：
  名称：

  Copper-Mediated Synthesis of Phthalocyanino-Fused Dehydro[12]- and [18]annulenes

  摘要：

  Cyclooligomeric phthalocyanines with the special feature of having a dehydroannulene core are described. Compounds 4a,b and 5a,b were prepared by an oxidative coupling mediated by copper from the corresponding diethynyl unsymmetrically substituted phthalocyanines 8a,b, which are easily accessible from the corresponding diiodo compounds 6a,b by a palladium-copper-catalyzed coupling. Appropriate conditions to Selectively form cyclodimers and cyclotrimers using Glaser and Eglinton methodologies have been attempted. In this way, two Compounds, 4a and 5b, each representative of a kind of oligomers, could be appropriately isolated and characterized by MALDI-MS. The W-vis spectra of compounds 4a and 5b show a split Q-band shifted to the red with respect to the corresponding precursor 8a,b. This can be interpreted,;in light of previous results, as a consequence of intramolecular electronic coupling between the Pc subunits. Extensive formation of aggregates in chloroform can be also inferred from the spectra. No significant differences could be observed in the spectra by comparison with that of the open-chain analogue II, most probably due to a saturation phenomenon of the optical properties already pointed out in the literature for other alkynyl-linked open-chain dimers.

  DOI：

  10.1021/jo0006019
• 作为产物：
  描述：

  4-氨基邻苯二甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 硫酸 、 二异丙胺 、 sodium nitrite 作用下， 反应 1.25h， 生成 4-(3-hydroxy-3-methyl-1-butynyl)phthalonitrile
  参考文献：
  名称：

  吡唑羧酸受体/锚定基团直接连接对酞菁敏化太阳能电池光伏性能的影响

  摘要：

  合成了一种不对称的酞菁锌染料 ( PCA-ZnPc-4 )，它含有六个供电子己硫基和一个与大环直接相连的吡唑-3-羧酸锚定基团，以评估其光物理、电化学和理论特性以及光伏特性。先前研究的染料PCA-ZnPc-2含有相同的给电子基团和具有桥氧原子的 pyrazole-3-羧酸锚定基团，用作参考染料。基于PCA-ZnPc-4的优化染料敏化太阳能电池 (DSSC)表现出令人印象深刻的 2.52% 的功率转换效率 ( J SC  = 6.53 mA cm -2 , V OC= 0.584 V, FF = 0.66), 超过相同条件下 基于PCA-ZnPc-2 (1.86%) 的 DSSC。PCA-ZnPc-4较好的光伏性能主要是由于其共轭的锚定基团，导致有效的电子注入。这项工作表明，在没有氧接头的情况下连接到大环上的锚定基团可以提高酞菁敏化太阳能电池的光伏性能。

  DOI：

  10.1016/j.dyepig.2022.110644

文献信息

• <i>o</i>-Carborane, Ferrocene, and Phthalocyanine Triad for High-Mobility Organic Field-Effect Transistors
  作者：Ilgın Nar、Armağan Atsay、Ahmet Altındal、Esin Hamuryudan

  DOI：10.1021/acs.inorgchem.7b03097

  日期：2018.2.19

  An unsymmetrical zinc phthalocyanine with ferrocenylcarborane linked to the phthalocyanine ring through a phenylethynyl spacer was designed for organic field-effect transistor (OFET). The unsymmetrical phthalocyanine derivatives were characterized using a wide range of spectroscopic and electrochemical methods. In particular, the ferrocenylcarborane structure was unambiguously revealed based on the

  为有机场效应晶体管（OFET）设计了不对称锌酞菁锌，其中二茂铁基碳硼烷通过苯基乙炔基间隔基连接到酞菁环上。使用多种光谱和电化学方法对不对称酞菁衍生物进行了表征。特别地，基于单晶X射线衍射分析清楚地揭示了二茂铁基碳环结构。对电化学性质的深入研究表明，二茂铁基碳环的插入扩展了二茂铁基碳烷取代的酞菁的电化学特性（7）。此外，在阳极电势扫描中，乙炔基酞菁（6）和7的氧化电聚合被记录。为了澄清ferrocenylcarborane（的插入的效果2）在场效应迁移率，溶液处理的膜2，6，和7被用作有源层以制造底栅顶接触OFET器件。对所制造装置的输出和转移特性的分析表明，用二茂铁基碳环烷部分官能化的酞菁衍生物在生产高迁移率的OFET中具有很大的潜力。
• Unusual mesomorphic behaviour of an ethynyl-substituted phthalocyanine
  作者：Eva M. García-Frutos、Giovanni Bottari、Purificación Vázquez、Joaquín Barberá、Tomás Torres

  DOI：10.1039/b604731a

  日期：——

  An ethynyl-substituted nickel(II) phthalocyanine has been synthesised and its thermotropic properties studied; optical microscopy, differential scanning calorimetry (DSC) and X-ray diffraction (XRD) techniques revealed an unusual mesomorphic behaviour observed for the first time in phthalocyanine systems where each disk of the hexagonal columnar mesophase is formed by two ethynyl-substituted phthalocyanine units.

  通过光学显微镜、差示扫描量热仪 (DSC) 和 X 射线衍射 (XRD) 技术，我们合成了一种乙炔基取代的酞菁镍（II），并研究了它的趋热特性，发现在酞菁体系中首次出现了一种不寻常的介形行为，即六方柱状介相的每个圆盘都是由两个乙炔基取代的酞菁单元形成的。
• Tuning Photoinduced Energy- and Electron-Transfer Events in Subphthalocyanine-Phthalocyanine Dyads
  作者：David González-Rodríguez、Christian G. Claessens、Tomas Torres、Shenggao Liu、Luis Echegoyen、Nuria Vila、Santi Nonell

  DOI：10.1002/chem.200400779

  日期：2005.6.20

  subphthalocyanine to the phthalocyanine takes place. On the contrary, stabilization of the radical pair by lowering the redox gap between electron donor and acceptor results in a highly efficient photoinduced electron-transfer process, even in solvents of low polarity such as toluene (Phi(ET) approximately 0.9). These features, together with the extraordinary absorptive cross section that these molecular ensembles

  通过单炔基酞菁与不同的单碘亚酞菁之间的钯催化的交叉偶联反应，已经制备了一系列的亚酞菁-酞菁二价化合物。两个光敏单元之间的电子耦合通过刚性和π共轭的炔基间隔基来确保。另外，通过引入不同的外围取代基来调节亚酞菁部分的电子特性。循环和Osteryoung方波伏安法实验表明，从硫醚或无取代基变为硝基时，该亚基的还原电势可降低约400 mV。结果，可以微调电荷转移状态的能级，以便获得对每个子单元中光激发能的命运的控制。所采用的各种稳态和时间分辨光物理技术表明，当电荷转移态处于高能量状态时，就会发生从激发的亚酞菁到酞菁的定量单重态单重态能量转移机理。相反，通过降低电子供体和受体之间的氧化还原间隙来稳定自由基对，即使在极性低的溶剂（例如甲苯（Phi（ET）约为0.9））中，也可以实现高效的光诱导电子转移过程。这些特征以及这些分子集合体在整个UV / Vis光谱中显示的非凡吸收性截面，使其成为需要宽带光源
• Alkynyl substituted phthalocyanine derivatives as targets for optical limiting
  作者：Eva M. García-Frutos、Sean M. O'Flaherty、Eva M. Maya、Gema de la Torre、Werner Blau、Purificación Vázquez、Tomás Torres

  DOI：10.1039/b210707d

  日期：2003.3.19

  One of the key issues in the development of efficient optical limiters is the search for appropriate materials with improved nonlinear absorption. Phthalocyanine materials are among the most promising nonlinear absorbers described in the literature. Ethynyl and butadiynyl-bridged bisphthalocyanines and related ethynyl-containing mononuclear compounds have been synthesized and experimentally studied using the z-scan technique with nanosecond pulses at 532 nm. We intend to ascertain the effect of the electronic interaction between macrocycles in the optical limiting performance of phthalocyanines.

  开发高效光学限幅器的一个关键问题是寻找具有改进的非线性吸收特性的合适材料。文献中描述的酞菁材料是最有前途的非线性吸收剂之一。我们已经合成并利用532 nm纳秒脉冲的z扫描技术对乙炔桥联双酞菁和相关的含乙炔单核化合物进行了实验研究。我们打算确定酞菁光学限幅性能中大环之间的电子相互作用的影响。
• Well-defined, persistent, chiral phthalocyanine nanoclusters via G-quadruplex assembly
  作者：Miguel García-Iglesias、Tomas Torres、David González-Rodríguez

  DOI：10.1039/c6cc04152c

  日期：——

  Monodisperse nanoclusters are produced via G-quadruplex assembly with potassium salts in which red-absorbing phthalocyanine dyes are arranged in a well-defined chiral organization.

  通过钾盐中的G四链体组装，形成具有单一粒径的纳米团簇，其中红吸收的酞菁染料以明确定义的手性排列。