2,8-dibromo-6,6,12,12-tetraethyl-6,12-dihydro-diindeno[1,2-b;1',2'-e]pyrazine | 1033616-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,8-dibromo-6,6,12,12-tetraethyl-6,12-dihydro-diindeno[1,2-b;1',2'-e]pyrazine
• 英文别名: 7,17-Dibromo-10,10,20,20-tetraethyl-2,12-diazapentacyclo[11.7.0.03,11.04,9.014,19]icosa-1,3(11),4(9),5,7,12,14(19),15,17-nonaene；7,17-dibromo-10,10,20,20-tetraethyl-2,12-diazapentacyclo[11.7.0.03,11.04,9.014,19]icosa-1,3(11),4(9),5,7,12,14(19),15,17-nonaene
• CAS: 1033616-81-7
• 化学式: C₂₆H₂₆Br₂N₂
• 分子量: 526.314
• InChiKey: PSAQOIUUTKJMJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,8-dibromo-6,6,12,12-tetraethyl-6,12-dihydro-diindeno[1,2-b;1',2'-e]pyrazine 、 3,5-双(三氟甲基)苯硼酸 在 palladium diacetate 、 四乙基氢氧化铵 、 三环己基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 以80%的产率得到2,8-bis(3,5-bis(trifluoromethyl)phenyl)-6,6,12,12-tetraethyl-6,12-dihydro-diindeno[1,2-b;1',2'-e]pyrazine
  参考文献：
  名称：

  Highly Induced Photoluminescense Indenopyrazine Derivatives

  摘要：

  We designed and synthesized new blue deep-blue photoluminescense materials base on indenopyrazine core. The synthesized materials are meta-positioned phenyl ring substituted by methyl (DMP-EIP), trifluoromethyl (TFDMP-EIP) and phenyl groups (DPP-EIP). These compounds also showed deep-blue PLmax values, 440 similar to 447 nm, in film state. But PL intensity in film state with same thickness was over about 8 similar to 10 times higher in TFDMP-EIP than DMP-EIP and DPP-EIP. TFDMP-EIP also showed about stronger PL intensity than DMP-EIP and DPP-EIP in PL spectrum and absolute quantum efficiency data.

  DOI：

  10.1080/15421406.2011.599700
• 作为产物：
  描述：

  溴乙烷 、 2,8-dibromo-6,12-dihydro-diindeno[1,2-b:1,2-e]pyrazine 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以54%的产率得到2,8-dibromo-6,6,12,12-tetraethyl-6,12-dihydro-diindeno[1,2-b;1',2'-e]pyrazine
  参考文献：
  名称：

  基于用于OLED的indenopyrazine芯新蓝紫色发射体：的位置的影响米三联苯侧基取代的光学和电致发光特性

  摘要：

  基于新的功能性核心，indenopyrazine基团A类有希望的蓝紫色发射器，已经成功地合成了在第一次通过用笨重取代米的三联苯侧基的邻位，间位，或对位的位置。合成的邻位和对位取代衍生物的紫外可见吸收光谱和PL光谱中的蓝移比间位衍生物的蓝移大取代的衍生物。分子计算证实了这些差异是由于衍生物的π-共轭长度随侧基连接到茚并吡嗪核上的位置而变化。当将合成的化合物用作非掺杂的OLED器件中的发光层时，观察到它们的光学性质相关的趋势。特别地，发现包含对位取代的衍生物的OLED具有优异的特性，具有423nm的最大EL发射，42nm的半峰全宽，具有CIE坐标（0.173，0.063）的纯紫光发射。外部量子效率为1.88％。

  DOI：

  10.1016/j.orgel.2010.01.030

文献信息

• New Deep Blue Emitting Materials Based on Indenopyrazine Core with High Thermal Stability
  作者：Chang-Hun Seok、Young-Il Park、Soo-Kang Kim、Ji-Hoon Lee、Jongwook Park

  DOI：10.1166/jnn.2011.3693

  日期：2011.5.1

  New deep blue emitting materials 2,8-bis(3,5-diphenylphenyl)-6,6,12,12-tetraethyl-6,12-dihydrodiindeno[1,2-b:1′,2′-e]pyrazine (DPP-EPY) and 2,8-bis(3′,5′-diphenylbiphenyl-4-yl)-6,6,12,12-tetraethyl-6,12-dihydrodiindeno[1,2-b:1′,2′-e]pyrazine (DPBP-EPY) were synthesized through introduction of m-terphenyl or triphenylbenzene bulky side groups in a new indenopyrazine core. These materials all showed high thermal stability and highly reduced intermolecular interaction. DPP-EPY and DPBP-EPY showed PL maxima of 456 nm and 460 nm in deep blue region and narrow PL spectra with full-width at half-maximum (FWHM) of 46 nm and 52 nm, respectively. As a result of making non-doped OLED devices using these synthesized materials as emitting layers, DPP-EPY showed EL spectrum of 452 nm, very narrow FWHM of 46 nm, luminance efficiency of 1.04 cd/A with current density of 10 mA/cm2 and CIE coordinate of (0.161, 0.104), creating a deep blue OLED close to the National Television System Committee (NTSC) blue standard.

  新的深蓝色发光材料2,8-双（3,5-二苯基苯基）-6,6,12,12-四乙基-6,12-二氢二茚并[1,2-b:1′,2′-e]吡嗪（DPP-EPY）和2,8-双（3′,5′-二苯基联苯-4-基）-6,6,12,12-四乙基-6,12-二氢二茚并[1,2-b:1′,2′-e]吡嗪（DPBP-EPY）是通过在茚并吡嗪新核心中引入间三联苯或三苯基苯大侧基合成的。这些材料均表现出高热稳定性和高度降低的分子间相互作用。DPP-EPY和DPBP-EPY在深蓝色区域显示出最大PL为456 nm和460 nm，且具有半高全宽（FWHM）分别为46 nm和52 nm的窄PL光谱。由于使用这些合成的材料作为发光层制造非掺杂OLED器件，DPP-EPY显示出452 nm的EL光谱，非常窄的FWHM为46 nm，在电流密度为10 mA/cm
• New blue-violet emitters based on an indenopyrazine core for OLEDs: Effects of the position of m-terphenyl side group substitution on optical and electroluminescence properties
  作者：Youngil Park、Sookang Kim、Ji-Hoon Lee、Dong Hyun Jung、Chung-Chih Wu、Jongwook Park

  DOI：10.1016/j.orgel.2010.01.030

  日期：2010.5

  m-terphenyl side groups in the ortho, meta, or para positions. There are larger blue shifts in the UV–visible absorption and PL spectra of the synthesized ortho- and para-substituted derivatives than in those of the meta-substituted derivative. Molecular calculations verified that these differences are due to the variation in the π-conjugation length of the derivatives with the position at which the

  基于新的功能性核心，indenopyrazine基团A类有希望的蓝紫色发射器，已经成功地合成了在第一次通过用笨重取代米的三联苯侧基的邻位，间位，或对位的位置。合成的邻位和对位取代衍生物的紫外可见吸收光谱和PL光谱中的蓝移比间位衍生物的蓝移大取代的衍生物。分子计算证实了这些差异是由于衍生物的π-共轭长度随侧基连接到茚并吡嗪核上的位置而变化。当将合成的化合物用作非掺杂的OLED器件中的发光层时，观察到它们的光学性质相关的趋势。特别地，发现包含对位取代的衍生物的OLED具有优异的特性，具有423nm的最大EL发射，42nm的半峰全宽，具有CIE坐标（0.173，0.063）的纯紫光发射。外部量子效率为1.88％。
• Highly Induced Photoluminescense Indenopyrazine Derivatives
  作者：Youngil Park、Ji-Hoon Lee、Jongwook Park

  DOI：10.1080/15421406.2011.599700

  日期：2011.11.4

  We designed and synthesized new blue deep-blue photoluminescense materials base on indenopyrazine core. The synthesized materials are meta-positioned phenyl ring substituted by methyl (DMP-EIP), trifluoromethyl (TFDMP-EIP) and phenyl groups (DPP-EIP). These compounds also showed deep-blue PLmax values, 440 similar to 447 nm, in film state. But PL intensity in film state with same thickness was over about 8 similar to 10 times higher in TFDMP-EIP than DMP-EIP and DPP-EIP. TFDMP-EIP also showed about stronger PL intensity than DMP-EIP and DPP-EIP in PL spectrum and absolute quantum efficiency data.