3-amino-5,12-diphenyl-6:7,10:11-(bis-benzo)tetracene-2-carboxylic acid | 1254184-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 3-amino-5,12-diphenyl-6:7,10:11-(bis-benzo)tetracene-2-carboxylic acid
• 英文别名: 3-amino-5,12-diphenyl-6:7,10:11-bisbenzotetracene-2-carboxylic acid；12-amino-9,14-diphenyldibenzo[de,qr]tetracene-11-carboxylic acid；7-Amino-3,10-diphenylhexacyclo[10.10.2.02,11.04,9.016,24.019,23]tetracosa-1(22),2,4,6,8,10,12,14,16(24),17,19(23),20-dodecaene-6-carboxylic acid
• CAS: 1254184-31-0
• 化学式: C₃₇H₂₃NO₂
• 分子量: 513.595
• InChiKey: OLQGPYYXYMCGRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  40
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-5,12-diphenyl-6:7,10:11-(bis-benzo)tetracene-2-carboxylic acid 、 3,6-二-2-吡啶基-1,2,4,5-四嗪 在 亚硝酸异戊酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以22%的产率得到9,16-diphenyl-11,14-di(pyridin-2-yl)-1,6-dihydrobenzo[8,9]triphenyleno[2,3-g]phthalazine
  参考文献：
  名称：

  [4 + 2]接近二氮杂双并戊酮的环加成反应：合成，结构，物理性质和自组装

  摘要：

  三个新的二氮杂双并戊并四（1,4,6,13-​​四苯基-7：8,11：12-双苯并-2,3-二氮杂双并五苯并茂（1，IUPAC名称：9,11,14,16-四苯基-1,6-二氢苯并[8,9] triphenyleno [2,3- g ] phthalazine）; 1,4-二（吡啶-2-基）-6,13-​​联苯-7：8,11：12-双苯并-2,3-二氮杂双并五苯（2，IUPAC名称：9，16-二苯基-11，14-二（吡啶-2-基）-1，6-二氢苯并[8，9]三苯基烯基[2，3- g ]邻苯二甲酰胺）；和1，4 -di（thien-2-yl）-6,13-​​diphenyl-7：8,11：12-bisbenzo-2,3-diazatwistpentacene（3，IUPAC名称：9,16-diphenyl-11,14-di（thien -2-yl）-1,6-dihydrobenzo [8,9]

  DOI：

  10.1021/jo500400d

文献信息

• Synthesis, structure, and optoelectronic properties of a new twistacene 1,2,3,4,6,13-hexaphenyl-7 : 8,11 : 12-bisbenzo-pentacene
  作者：Jinchong Xiao、Yoga Divayana、Qichun Zhang、Hieu M. Doung、Hua Zhang、Freddy Boey、Xiao Wei Sun、Fred Wudl

  DOI：10.1039/c0jm01460e

  日期：——

  We report the synthesis, optical and electrochemical properties, as well as the fabrication of light-emitting devices for a new twistacene 1,2,3,4,6,13-hexaphenyl-7 : 8,11 : 12-bisbenzo-pentacene (HBP 1). Its structure, determined by X-ray crystallography, confirmed that this material has a twisted topology with the torsion angle as high as 23.0°. HBP 1 showed bright green emission both in solution and solid state. The HOMO–LUMO gap of HBP 1 calculated from the difference between the half-wave redox potentials (E1/2ox = +0.74 eV and E1/2red = −1.93 eV) is 2.67 eV, which is in good agreement with the band gap, 2.64 eV, derived from the UV-Vis absorption data. Organic light emitting devices using HBP 1 as the emitters have been fabricated. The results revealed that twistacenes are promising materials to enhance the efficiency of OLEDs.

  我们报道了一种新的扭曲苊烯1,2,3,4,6,13-六苯基-7 : 8,11 : 12-双苯并五苊烯(HBP 1)的合成、光学和电化学特性，以及其发光器件的制造。通过X射线晶体学确定的其结构确认该材料具有扭曲的拓扑结构，扭转角高达23.0°。HBP 1在溶液和固态下均表现出明亮的绿色发光。根据半波氧化还原电位(E1/2ox = +0.74 eV和E1/2red = -1.93 eV)的差值计算，HBP 1的HOMO-LUMO间隙为2.67 eV，与从UV-Vis吸收数据推导出的带隙2.64 eV非常吻合。已制造了以HBP 1作为发光材料的有机发光器件。结果表明，扭曲苊烯是提高OLED效率的有前景材料。
• “Clean Reaction” Strategy to Approach a Stable, Green Heptatwistacene Containing a Single Terminal Pyrene Unit
  作者：Jinchong Xiao、Christos D. Malliakas、Yi Liu、Feng Zhou、Gang Li、Haibin Su、Mercouri G. Kanatzidis、Fred Wudl、Qichun Zhang

  DOI：10.1002/asia.201100910

  日期：2012.4

  Let's twist again: A “clean reaction” strategy based on thermally eliminating lactam bridges from a soluble acene precursor through a retro‐Diels–Alder reaction gives a new, stable, green heptatwistacene (see structure). The molecule has a twist angle of 23.49°, is very stable even in air, and has an optical band gap of 1.82 eV.

  让我们再扭转一下：一种“清洁反应”策略，其基础是通过逆Diels-Alder反应从可溶性并苯前驱体中消除内酰胺桥，从而产生一种新的，稳定的绿色七紫杉醇（参见结构）。该分子的扭曲角为23.49°，即使在空气中也非常稳定，并且光学带隙为1.82 eV。
• Approaching a stable, green twisted heteroacene through “clean reaction” strategy
  作者：Gang Li、Hieu M. Duong、Zhonghan Zhang、Jinchong Xiao、Lei Liu、Yanli Zhao、Hua Zhang、Fengwei Huo、Shuzhou Li、Jan Ma、Fred Wudl、Qichun Zhang

  DOI：10.1039/c2cc32048g

  日期：——

  A new, longest, stable, green twisted heteroacene 2-methyl-1,4,6,13-tetraphenyl-7:8,11:12-bisbenzo-anthro[g]isoquinolin-3(2H)-one (3) was synthesized by employing a “clean reaction” strategy based on thermally eliminating lactam bridges. Calculation shows that the HOMO–LUMO bandgap is in good agreement with experimental data.

  一种新的、最长、稳定、绿色扭曲的杂环烯2-甲基-1,4,6,13-四苯基-7:8,11:12-双苯并-蒽并[g]异喹啉-3(2H)-酮(3)是通过采用基于热消除内酰胺桥的“清洁反应”策略合成的。计算表明，HOMO-LUMO带隙与实验数据非常吻合。
• Synthesis and Structure Characterization of a Stable Nonatwistacene
  作者：Jinchong Xiao、Hieu M. Duong、Yi Liu、Wenxiong Shi、Li Ji、Gang Li、Shuzhou Li、Xue-Wei Liu、Jan Ma、Fred Wudl、Qichun Zhang

  DOI：10.1002/anie.201200949

  日期：2012.6.18

  eliminating lactam bridges from a soluble acene precursor through a retro‐Diels–Alder reaction, led to the synthesis and characterization of a novel, stable, green crystalline 6,8,10,17,19,21‐hexaphenyl‐1.22,4.5,11.12,15.16‐tetrabenzononatwistacene. An analysis of the single crystal structure of the nonatwistacene indicates that this molecule is twisted at an angle of 25.44°.

  一种干净的反应策略，其基础是通过逆Diels-Alder反应从可溶性并苯前体中消除内酰胺桥，从而合成并表征了新颖，稳定的绿色结晶6,8,10,17,19,21-六苯基-1.22,4.5,11.12,15.16-四苯并壬基并四苯。对九碳四烯并苯的单晶结构的分析表明，该分子以25.​​44°的角度扭曲。
• Synthesis, Structure, and Physical Properties of 5,7,14,16-Tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene
  作者：Jinchong Xiao、Shuwei Liu、Yi Liu、Li Ji、Xuewei Liu、Hua Zhang、Xiaowei Sun、Qichun Zhang

  DOI：10.1002/asia.201100733

  日期：2012.3.5

  A novel compound, 5,7,14,16‐tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene (TBH), has been successfully synthesized through a retro‐Diels–Alder reaction. Single‐crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The HOMO–LUMO gap of TBH calculated from the difference between the half‐wave redox potentials (E1/2ox=+0.40 eV and E1/2red=−1.78 eV) is

  通过逆狄尔斯-阿尔德反应已成功合成了一种新型化合物5,7,14,16-四苯基-8：9,12：13-双苯并六十六碳四烯（TBH）。单晶结构分析表明，TBH具有扭曲结构，扭转角为27.34°。由半波氧化还原电势（E 1/2 ox = + 0.40 eV和E 1/2 red = −1.78 eV）之间的差计算得出的TBH的HOMO-LUMO间隙为2.18 eV，与由UV / Vis吸收数据得出的带隙（2.19 eV）。此外，还制造了使用TBH作为发射器的有机发光器件。结果表明，TBH 是有机发光二极管应用中有希望的红色发光候选物。