1,3,5-tris(4-(4-ethynylbenzonitrile)phenyl)benzene | 246247-35-8

• 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-(4-ethynylbenzonitrile)phenyl)benzene
• 英文别名: 1,3,5-tris{4-[(4-cyano)phenylethynyl]phenyl}benzene；4-[2-[4-[3,5-Bis[4-[2-(4-cyanophenyl)ethynyl]phenyl]phenyl]phenyl]ethynyl]benzonitrile
• CAS: 246247-35-8
• 化学式: C₅₁H₂₇N₃
• 分子量: 681.795
• InChiKey: QGBYEKBFFZGECS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  54
• 可旋转键数：
  9
• 环数：
  7.0
• 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-(4-ethynylbenzonitrile)phenyl)benzene 以 苯 为溶剂， 生成 silver triflate*1,3,5-tris(4-(4-ethynylbenzonitrile)phenyl)benzene
  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：

  1,3,5-三(4-溴苯基)苯 、 4-乙炔基苯甲腈 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 16.0h， 以37%的产率得到1,3,5-tris(4-(4-ethynylbenzonitrile)phenyl)benzene
  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

文献信息

• Template-Directed Synthesis, Excited-State Photodynamics, and Electronic Communication in a Hexameric Wheel of Porphyrins
  作者：Junzhong Li、Arounaguiry Ambroise、Sung Ik Yang、James R. Diers、Jyoti Seth、Christopher R. Wack、David F. Bocian、Dewey Holten、Jonathan S. Lindsey

  DOI：10.1021/ja991730d

  日期：1999.9.1

  architecture (cyclo-Zn3Fb3U-p/m) has been prepared that is comprised of three free base (Fb) porphyrins and three zinc porphyrins linked at the meso-positions via diphenylethyne units. The synthesis involves the Pd-mediated coupling of a p/p-substituted diethynyl Zn porphyrin and a m/m-substituted diiodo Fb porphyrin, forming p/m-substituted diphenylethyne linkages. The isolated yield of cyclo-Zn3Fb3U-p/m

  为了研究分子光子学应用的新结构，制备了一种形状持久的环状六聚体结构 (cyclo-Zn3Fb3U-p/m)，它由三个游离碱 (Fb) 卟啉和三个通过中间位置连接的锌卟啉组成二苯乙炔单元。该合成涉及 Pd 介导的 p/p 取代二乙炔基锌卟啉和 am/m 取代二碘 Fb 卟啉的偶联，形成 p/m 取代二苯乙炔键。在三吡啶基模板存在下，环-Zn3Fb3U-p/m 的分离产率为 5.3%。该阵列具有 C3v 对称性，最短路径上有 108 个原子，整个腔体的面对面距离约为 35 A。环-Zn3Fb3U-p/m 中锌卟啉的激发态寿命为 17 ps，给出每个相邻 Fb 卟啉的能量转移率为 ktrans = (34 ps)-1 和 Φtrans = 99.2% 的量子效率。该速率与具有相同接头的二聚体 (ZnFbU-p/m) 相当，但比 ap/p 连接的 ZnFb 二聚体慢，...