1,3,5-tris(4-cyanophenylethynyl)benzene | 167497-13-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,3,5-tris(4-cyanophenylethynyl)benzene
• 英文别名: 4-[2-[3,5-Bis[2-(4-cyanophenyl)ethynyl]phenyl]ethynyl]benzonitrile
• CAS: 167497-13-4
• 化学式: C₃₃H₁₅N₃
• 分子量: 453.502
• InChiKey: KBUUKJDGRPYVKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  silver trifluoromethanesulfonate 、 1,3,5-tris(4-cyanophenylethynyl)benzene 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Variable Pore Size, Variable Chemical Functionality, and an Example of Reactivity within Porous Phenylacetylene Silver Salts

  摘要：

  Investigations on molecular variants of the 3-fold symmetric 1,3,5-tris(4-ethynylbenzonitrile)benzene crystallized with silver triflate revealed a nearly invariant pseudohexagonal porous structure type. Modifications involved the attachment of pendant groups to the central aromatic ring of the parent molecule. Pendant groups include the vinyl group, stilbene, the chiral group myrtanol, and groups with different chemical functionalities such as alcohols, ethers, and esters. Modifications also included the addition of elongated spacer units between the central benzene ring and the peripheral nitrile groups. In these molecules the acetylene bridges of 1,3,5-tris(4-ethynylbenzonitrile)benzene were replaced with diacetylene, ethynylbenzene, and diethynylbenzene type units. Single-crystal refinements for pentoxy-2,4,6-tris(4-ethynylbenzonitril)benzene.AgOTf and 1,3,5-tris(4-(4-ethynylbenzonitrile)phenyl)benzene.AgOTf as well as powder data on 12 crystalline phases showed the consistent formation of pseudohexagonal channels, demonstrating that the parent porous architecture is stable both to functional modification of the interior of the channel as well as to enlargement of the pores. Pentoxy-2,4,6-tris(4-ethynylbenzonitrile)benzene.AgOTf refined in the monoclinic space group Am. 1,3,5-Tris(4-(4-ethynylbenzonitrile)phenyl)benzene.AgOTf was found to be triclinic with space group P (1) over bar. These crystals have pseudohexagonal channels respectively 15 and 25 Angstrom in diameter. Cell constants based on powder data are compatible with channel diameters ranging from 10 to 30 Angstrom. The latter channel diameters are among the largest known for organic porous solids. The introduction of the chiral myrtanol unit led to the preparation of a chiral porous solid. The thermal and chemical stabilities of these phases were investigated. The pseudohexagonal structure proved stable to complete solvent loss from the channel. It was found in the case of a host with alcohol functionality that an acid anhydride guest, trifluoroacetic anhydride, reacted with the host to form an ester with retention of the porous structure type.

  DOI：

  10.1021/ja991100b
• 作为产物：
  描述：

  4,4’,4’’-[苯-1,3,5-三基三(乙炔-2,1-二基)]三苯甲醛 在 potassium tert-butylate 、 1-amino-1,4-diazabicyclo[2.2.2]octane-1,4-diium iodide 作用下， 以 四氢呋喃 为溶剂， 以78 %的产率得到1,3,5-tris(4-cyanophenylethynyl)benzene
  参考文献：
  名称：

  一种醛基快速转化为氰基的方法

  摘要：

  本发明公开了一种醛基快速转化为氰基的方法。所述方法包括：提供醛类化合物，使包含醛类化合物、胺化试剂、碱性物质和溶剂的混合反应体系进行反应，制得腈类化合物。本发明提供的方法反应操作简单，可以在空气与少量水分的环境下进行，反应条件温和、高效，具有良好的官能团兼容性；所制得的腈类化合物在生物、医药、材料等领域有着重要的作用。

  公开号：

  CN115724706A

文献信息

• 1,3,5-Tris(functionalised-phenylethynyl)benzene–metal complexes: synthetic survey of mesoporous coordination polymers and investigation of their carbonisation
  作者：Norifumi Kobayashi、Masashi Kijima

  DOI：10.1039/b715550f

  日期：——

  A series of multicoordinate 1,3,5-tris(functionalised-phenylethynyl)benzenes (1–9) was synthesised, and coordination polymers were constructed from these organic linkers and copper ions in high yields. The carbonisation of the linkers 1–9 afforded a microporous carbon that shows type I adsorption–desorption isotherm. Although most of the coordination polymers prepared in this study turned out to be low porous materials, the coordination polymer 7e prepared from the reaction of 1,3,5-tris(4-carboxyphenylethynyl)benzene tripotassium salt (K37) and copper(II) nitrate was a microporous material in addition to the mesoporous materials (7c and 7d) prepared from the reaction of K37 with copper(II) acetate and copper(II) chloride, respectively. The carbonisation of the coordination polymers unexceptionally brought about an increase of micropore volume. A stepwise analysis of 7c pyrolysed at 350, 600, and 900 °C revealed that the mesoporosity hardly changed upon heat treatment, which in other words, demonstrates that microporosity could be successfully added to the mesoporous coordination polymer through the carbonisation process.

  合成了一系列多坐标的1,3,5-三（功能化苯乙炔基）苯（1–9），并从这些有机连接体和铜离子构建了高产率的配位聚合物。连接体1–9的炭化产出了表面展现出I型吸附-解吸等温线的微孔碳。尽管本研究中制备的大多数配位聚合物最终成为低孔材料，但通过1,3,5-三（4-羧基苯乙炔基）苯三钾盐（K37）与硝酸铜（II）反应生成的配位聚合物7e除了还得到了与K37分别与醋酸铜（II）和氯化铜（II）反应而制得的中孔材料（7c和7d）。配位聚合物的炭化无例外地导致微孔体积的增加。对在350、600和900 ℃下热解的7c进行的逐步分析揭示，热处理后中孔率几乎没有改变，换句话说，这表明微孔率可以通过炭化过程成功地添加到中孔配位聚合物中。
• Visible-Light Photolytic Synthesis of Multinuclear and Dendritic Iron-Nitrile Cationic Complexes
  作者：Cátia Ornelas、Jaime Ruiz、João Rodrigues、Didier Astruc

  DOI：10.1021/ic800100k

  日期：2008.5.19

  piano-stool cationic complexes were synthesized in quantitative yield by a single-step synthesis involving visible-light photolysis of the complex [CpFe(eta(6)-toluene)][PF6]. This synthetic strategy was applied to mono-, bis- and tris-nitrile ligands and to new nitrile-terminated dendrimers containing 9, 27, and 81 tethers. All the synthesized products are deep red solids or red waxy products, highly

  多核和树枝状铁腈钢琴凳式阳离子配合物是通过涉及可见光光解[CpFe（eta（6）-甲苯）] [PF6]的一步合成以定量收率合成的。这种合成策略适用于单，双和三腈配体，也适用于含有9个，27个和81个系链的新的腈封端的树状聚合物。所有合成的产品均为深红色固体或红色蜡状产品，对空气和湿气高度稳定。它们的特征在于（1）H，（13）C和（31）P NMR，元素分析，紫外-可见光谱和循环伏安法（对Fe（III）的单个可逆氧化波）。仅对二取代的芳烃二腈二铁配合物显示出两个分离的可逆波，表明铁中心之间通过腈配体进行一些电子通讯。
• Rigid Molecular Architectures That Comprise a 1,3,5-Trisubstituted Benzene Core and Three Oligoaryleneethynylene Arms:  Light-Emitting Characteristics and π Conjugation between the Arms
  作者：Yoshihiro Yamaguchi、Takanori Ochi、Satoshi Miyamura、Takahiro Tanaka、Shigeya Kobayashi、Tateaki Wakamiya、Yoshio Matsubara、Zen-ichi Yoshida

  DOI：10.1021/ja057751r

  日期：2006.4.1

  In view of increasing interest in light-emitting materials, we have investigated the light-emitting characteristics and occurrence of conjugation between arms of star-shaped rigid molecules that comprise a 1,3,5-triethynylbenzene core and methoxy group-substituted oligo(p-phenylethynylene) arms. Consequently, we achieved the ultimate goal (Phif approximately 1.0, log epsilon > 5) for organic molecules with respect to light-emitting ability by creating very intense violet-blue (8, Phif = 0.97, log epsilon = 5.11) and blue (9, Phif = 0.98, log epsilon = 5.29) bright light-emitters. Also, pi conjugation was found to occur between the arms of 9 despite the meta-substituted system. We found a linear relationship of kr (with positive slope) and kd (with negative slope) with the number of dimethoxyphenyleneethynylene units for MMPT (4, 6, 8) and DMPT (5, 7, 9) homologues and the contrasting solvent effect on lambdaem of 8 and 9. It is also interesting that lambdaabs, epsilon, lambdaem, and Phif of 9 are greater than those of the corresponding banana- and rod-shaped molecules.