3,3',5,5'-tetraethynyl-2,2',4,4',6,6'-hexamethylbiphenyl | 1093856-18-8

• 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: 3,3',5,5'-tetraethynyl-2,2',4,4',6,6'-hexamethylbiphenyl
• 英文别名: 3,3',5,5'-tetraethynylbimesityl；3,3',5,5'-Tetraethynyl-2,2',4,4',6,6'-hexamethyl-1,1'-biphenyl；1-(3,5-diethynyl-2,4,6-trimethylphenyl)-3,5-diethynyl-2,4,6-trimethylbenzene
• CAS: 1093856-18-8
• 化学式: C₂₆H₂₂
• 分子量: 334.461
• InChiKey: CLIBDSXLQWBCQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,3',5,5'-tetraethynyl-2,2',4,4',6,6'-hexamethylbiphenyl 、 10-溴-9-(苯基乙炔基)蒽 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以54%的产率得到C₁₁₄H₇₀
  参考文献：
  名称：

  De Novo Design for Functional Amorphous Materials: Synthesis and Thermal and Light-Emitting Properties ofTwistedAnthracene-Functionalized Bimesitylenes

  摘要：

  The unique structural attributes inherent to D-2d-symmetric rigid tetraarylbimesityls render their close packing in the solid state difficult. We have exploited the indisposed tendency of such modules based on the bimesityl scaffold toward crystallization to design a novel class of amorphous functional materials with high glass transition temperatures and thermal stability (T-d > 400 degrees C). It is shown that a variety of 2- and 4-fold anthracene-functionalized bimesityls, 1-7, that exhibit excellent amorphous properties (T-g = ca. 190-330 degrees C) can be readily prepared via facile Pd(0)-mediated cross-coupling strategies. As the communication between the bimesityl core and the anchored anthracenes is negligible or only marginal, the trends observed for luminescence of model constituent anthracenes are reproduced in the condensed-phase photoluminescence and electroluminescence of 1-7. In other words, the emission characteristics, i.e., lambda(max) and quantum yields, are readily modulated via appropriate modification of the fluorophores. The functional behavior of this unique class of amorphous materials based on the bimesityl scaffold is demonstrated by fabrication of OLED devices. The 2-fold functionalized derivatives 1 and 2 lend themselves to sublimation techniques, so that the electroluminescence is captured with high efficiencies at low turn-on voltages (3.5-6.5 V). The device ITO/NPB (400 angstrom)/1 % 2:MADN (400 angstrom)/TPBI (400 angstrom)/LiF (10 angstrom)/Al (1500 angstrom) for 2 yields the, highest luminance of similar to 13 900 cd/m(2) at 17.5 V, a maximum luminance efficiency of similar to 7.4 cd/A at 4.5 V, and a power efficiency of similar to 5.3 lm/W at 4.0 V. Further, at a brightness of 800 cd/m(2) and a current density of 13.8 mA/cm(2), the device is found to exhibit excellent luminance efficiency of 5.8 cd/A, external quantum efficiency of 4.3% with a power efficiency of 2.2 Im/W, and pure blue light with a CIEx,y (x = 0.13, y = 0.18). The performance characteristics of the devices fabricated for 1 and 2 are remarkable. Although the 4-fold functionalized systems did not permit sublimation leading to spin-coating as a means for device fabrication, the observed electroluminescence for 4 and 5 attests to a broader scope and applicability of this new category of amorphous molecules for application in OLEDs.

  DOI：

  10.1021/ja8042905
• 作为产物：
  描述：

  3,3',5,5'-tetrakis[(trimethylsilyl)ethynyl]-bimesityl 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到3,3',5,5'-tetraethynyl-2,2',4,4',6,6'-hexamethylbiphenyl
  参考文献：
  名称：

  De Novo Design for Functional Amorphous Materials: Synthesis and Thermal and Light-Emitting Properties ofTwistedAnthracene-Functionalized Bimesitylenes

  摘要：

  The unique structural attributes inherent to D-2d-symmetric rigid tetraarylbimesityls render their close packing in the solid state difficult. We have exploited the indisposed tendency of such modules based on the bimesityl scaffold toward crystallization to design a novel class of amorphous functional materials with high glass transition temperatures and thermal stability (T-d > 400 degrees C). It is shown that a variety of 2- and 4-fold anthracene-functionalized bimesityls, 1-7, that exhibit excellent amorphous properties (T-g = ca. 190-330 degrees C) can be readily prepared via facile Pd(0)-mediated cross-coupling strategies. As the communication between the bimesityl core and the anchored anthracenes is negligible or only marginal, the trends observed for luminescence of model constituent anthracenes are reproduced in the condensed-phase photoluminescence and electroluminescence of 1-7. In other words, the emission characteristics, i.e., lambda(max) and quantum yields, are readily modulated via appropriate modification of the fluorophores. The functional behavior of this unique class of amorphous materials based on the bimesityl scaffold is demonstrated by fabrication of OLED devices. The 2-fold functionalized derivatives 1 and 2 lend themselves to sublimation techniques, so that the electroluminescence is captured with high efficiencies at low turn-on voltages (3.5-6.5 V). The device ITO/NPB (400 angstrom)/1 % 2:MADN (400 angstrom)/TPBI (400 angstrom)/LiF (10 angstrom)/Al (1500 angstrom) for 2 yields the, highest luminance of similar to 13 900 cd/m(2) at 17.5 V, a maximum luminance efficiency of similar to 7.4 cd/A at 4.5 V, and a power efficiency of similar to 5.3 lm/W at 4.0 V. Further, at a brightness of 800 cd/m(2) and a current density of 13.8 mA/cm(2), the device is found to exhibit excellent luminance efficiency of 5.8 cd/A, external quantum efficiency of 4.3% with a power efficiency of 2.2 Im/W, and pure blue light with a CIEx,y (x = 0.13, y = 0.18). The performance characteristics of the devices fabricated for 1 and 2 are remarkable. Although the 4-fold functionalized systems did not permit sublimation leading to spin-coating as a means for device fabrication, the observed electroluminescence for 4 and 5 attests to a broader scope and applicability of this new category of amorphous molecules for application in OLEDs.

  DOI：

  10.1021/ja8042905

文献信息

• Rational Design and Synthesis of Porous Polymer Networks: Toward High Surface Area
  作者：Weigang Lu、Zhangwen Wei、Daqiang Yuan、Jian Tian、Stephen Fordham、Hong-Cai Zhou

  DOI：10.1021/cm501922h

  日期：2014.8.12

  Head-on polymerization of tetrahedral monomers inherently imparts interconnected diamond cages to the resulting framework with each strut widely exposed. We have designed and synthesized a series of 3,3',5,5'-tetraethynylbiphenyl monomers, in which the two phenyl rings are progressively locked into a nearly perpendicular position by adding substituents of different size at 2, 2', 6, and 6' positions, as evident from single crystal structures. Computational simulation suggests that these monomers, though not perfectly regular tetrahedra, could still be self-polymerized into three-dimensional frameworks with the same topology. Indeed, five porous polymer networks (PPNs) have been successfully synthesized with these newly designed monomers through Cu(II)-promoted Eglinton homocoupling reaction. Among them, PPN-13 shows exceptionally high Brunauer-Emmett-Teller (BET) surface area of 3420 m(2)/g. The total hydrogen uptake is 52 mg/g at 40 bar and 77 K, and the total methane uptake is 179 mg/g at 65 bar and 298 K.
• De Novo Design for Functional Amorphous Materials: Synthesis and Thermal and Light-Emitting Properties of<i>Twisted</i>Anthracene-Functionalized Bimesitylenes
  作者：Jarugu Narasimha Moorthy、Parthasarathy Venkatakrishnan、Palani Natarajan、Duo-Fong Huang、Tahsin J. Chow

  DOI：10.1021/ja8042905

  日期：2008.12.24

  The unique structural attributes inherent to D-2d-symmetric rigid tetraarylbimesityls render their close packing in the solid state difficult. We have exploited the indisposed tendency of such modules based on the bimesityl scaffold toward crystallization to design a novel class of amorphous functional materials with high glass transition temperatures and thermal stability (T-d > 400 degrees C). It is shown that a variety of 2- and 4-fold anthracene-functionalized bimesityls, 1-7, that exhibit excellent amorphous properties (T-g = ca. 190-330 degrees C) can be readily prepared via facile Pd(0)-mediated cross-coupling strategies. As the communication between the bimesityl core and the anchored anthracenes is negligible or only marginal, the trends observed for luminescence of model constituent anthracenes are reproduced in the condensed-phase photoluminescence and electroluminescence of 1-7. In other words, the emission characteristics, i.e., lambda(max) and quantum yields, are readily modulated via appropriate modification of the fluorophores. The functional behavior of this unique class of amorphous materials based on the bimesityl scaffold is demonstrated by fabrication of OLED devices. The 2-fold functionalized derivatives 1 and 2 lend themselves to sublimation techniques, so that the electroluminescence is captured with high efficiencies at low turn-on voltages (3.5-6.5 V). The device ITO/NPB (400 angstrom)/1 % 2:MADN (400 angstrom)/TPBI (400 angstrom)/LiF (10 angstrom)/Al (1500 angstrom) for 2 yields the, highest luminance of similar to 13 900 cd/m(2) at 17.5 V, a maximum luminance efficiency of similar to 7.4 cd/A at 4.5 V, and a power efficiency of similar to 5.3 lm/W at 4.0 V. Further, at a brightness of 800 cd/m(2) and a current density of 13.8 mA/cm(2), the device is found to exhibit excellent luminance efficiency of 5.8 cd/A, external quantum efficiency of 4.3% with a power efficiency of 2.2 Im/W, and pure blue light with a CIEx,y (x = 0.13, y = 0.18). The performance characteristics of the devices fabricated for 1 and 2 are remarkable. Although the 4-fold functionalized systems did not permit sublimation leading to spin-coating as a means for device fabrication, the observed electroluminescence for 4 and 5 attests to a broader scope and applicability of this new category of amorphous molecules for application in OLEDs.