Pyrene-1,6-diyldiboronic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: Pyrene-1,6-diyldiboronic acid
• 英文别名: pyren-1,6-diboronic acid；pyrene-1,6-diboronic acid；1,6-pyrenyldiboronic acid；Boronic acid, 1,6-pyrenediylbis-；(6-boronopyren-1-yl)boronic acid
• 化学式: C₁₆H₁₂B₂O₄
• 分子量: 289.891
• InChiKey: DEZKYUTZVIMPGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴-2,2'-联吡啶 、 Pyrene-1,6-diyldiboronic acid 在 bis-triphenylphosphine-palladium(II) chloride calcium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到2-吡啶-2-基-4-[6-(2-吡啶-2-基吡啶-4-基)芘-1-基]吡啶
  参考文献：
  名称：

  Tunable Photophysical Properties of Two 2,2‘-Bipyridine-Substituted Pyrene Derivatives

  摘要：

  Two fluorescent pyrene derivatives, I and II, are reported in which the aromatic ring is connected to the 2,2'-bipyridine (bpy) complexing unit via a single C-C bond. Compound I contains one bpy moiety at the 1 position of the pyrene nucleus while II bears two bpy moieties linked to the 1 and 6 vertexes. The solvent-polarity dependence of the fluorescence emission properties of both compounds at room temperature points to the existence of a polar excited-state possessing a small extent of intramolecular charge transfer (ICT). The large fluorescence quantum yields, Phi (f), the high radiative rate constants, k(f), and the short fluorescence lifetimes, tau (f), for both compounds are characteristic of strongly allowed transitions. The solvent and temperature dependence of the photophysical properties of I, such as the increase of k(f) with increasing polarity and temperature, appears to be due to intermixing between closely lying polar S-1(L-1(a)) and forbidden S-2(L-1(b)) states. Semiempirical theoretical calculations were performed for I and allowed to confirm the assignment of the electronic and structural nature of the two lowest-energy excited states as a function of the interannular dihedral angle. In contrast, the experimental and calculated properties for compound II point to the occurrence of a highly stabilized L-1(a)-type excited state, thus experiencing very little influence of the forbidden L-1(b)-type state. Consistently, the fluorescence emission rate constant for II is found to be independent of solvent polarity and temperature.

  DOI：

  10.1021/jp000658z

文献信息

• 一种基于芘-噁二唑衍生物的双极性化合物及其应用
  申请人：瑞声科技（南京）有限公司

  公开号：CN108947926A

  公开（公告）日：2018-12-07

  本发明涉及有机电致发光技术领域，公开了一种基于芘‑噁二唑衍生物的双极性化合物及其应用。本发明所公开的双极性化合物具有如通式(I)、(II)或(III)所示的结构。本发明提供的化合物基于芘‑噁二唑骨架，具有空穴/电子传输平衡的双极性特性，并且具有较好的空穴、电子注入能力及能级匹配，整个分子的空穴、电子传输速率得到有效调整，尤其适合应用于OLED、OFT、OPV、QLED等技术领域。
• 一种含芘类结构的化合物及其有机发光器件
  申请人：长春海谱润斯科技有限公司

  公开号：CN109180569A

  公开（公告）日：2019-01-11

  本发明公开了一种含芘类结构的化合物及其有机发光器件，芘环结构与芴烯基团结合形成的一种含芘类结构的化合物，一方面，拥有可伸展的三维结构，使得这类化合物在空间立体结构上有一定的扭曲，提高其成膜性；另一方面，芘环结构具有较高的三线态能级和较宽的能隙，表现出性能优异的蓝光性能，将其与吸电子性能的芴烯相连，红移后发出绿光或红光。而且，此化合物具有合适的HOMO和LUMO值，有效的阻挡空穴向电子传输层的传输，从而提高其有效发光。将其应用于有机发光器件，作为发光层或空穴阻挡层使用，器件表现出驱动电压低、发光效率高的优点。
• 一种基于芘-三氮唑衍生物的双极性化合物及其应用
  申请人：瑞声科技（南京）有限公司

  公开号：CN108822049A

  公开（公告）日：2018-11-16

  本发明涉及有机电致发光器件技术领域，公开了一种基于芘‑三氮唑衍生物的双极性化合物及其在器件中的应用。本发明所公开的双极性化合物具有如通式(I)、(II)或(III)所示的结构。本发明提供的化合物基于芘‑三氮唑骨架，其具有空穴、电子传输平衡的双极性特性，并且具有较好的空穴、电子注入能力及能级匹配，整个分子的空穴/电子传输速率得到有效调整，载流子在S1至S0的跃迁阵子强度值大于或等于0.5，尤其适合应用于OLED、OFT、OPV、QLED等技术领域。
• 一种芘类化合物以及包含其的有机电致发光器件
  申请人：石家庄诚志永华显示材料有限公司

  公开号：CN117777202A

  公开（公告）日：2024-03-29

  本发明提供一种芘类化合物以及包含其的有机电致发光器件，所述化合物的结构通式如式I所示，其中，Ar1为被氮取代的碳原子数为10至60的稠环杂芳基。该芘类化合物不仅具有优异的电荷生成能力，还具有优异的配位能力，能够与各种金属掺杂剂络合，将本发明提供的芘类化合物作为电荷产生层材料应用于叠层器件，该芘类化合物能够有效避免由于电荷生成能力不足而导致的载流子传输不平衡的问题，进而能够有效提高叠层器件的效率，克服了现有技术的缺陷。#imgabs0#
• Tunable Photophysical Properties of Two 2,2‘-Bipyridine-Substituted Pyrene Derivatives
  作者：Tirapattur Soujanya、Annie Philippon、Stéphanie Leroy、Martine Vallier、Frédéric Fages

  DOI：10.1021/jp000658z

  日期：2000.10.1

  Two fluorescent pyrene derivatives, I and II, are reported in which the aromatic ring is connected to the 2,2'-bipyridine (bpy) complexing unit via a single C-C bond. Compound I contains one bpy moiety at the 1 position of the pyrene nucleus while II bears two bpy moieties linked to the 1 and 6 vertexes. The solvent-polarity dependence of the fluorescence emission properties of both compounds at room temperature points to the existence of a polar excited-state possessing a small extent of intramolecular charge transfer (ICT). The large fluorescence quantum yields, Phi (f), the high radiative rate constants, k(f), and the short fluorescence lifetimes, tau (f), for both compounds are characteristic of strongly allowed transitions. The solvent and temperature dependence of the photophysical properties of I, such as the increase of k(f) with increasing polarity and temperature, appears to be due to intermixing between closely lying polar S-1(L-1(a)) and forbidden S-2(L-1(b)) states. Semiempirical theoretical calculations were performed for I and allowed to confirm the assignment of the electronic and structural nature of the two lowest-energy excited states as a function of the interannular dihedral angle. In contrast, the experimental and calculated properties for compound II point to the occurrence of a highly stabilized L-1(a)-type excited state, thus experiencing very little influence of the forbidden L-1(b)-type state. Consistently, the fluorescence emission rate constant for II is found to be independent of solvent polarity and temperature.