2-(4-(di(mesityl)boryl)phenyl)quinoline | 332350-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-(di(mesityl)boryl)phenyl)quinoline
• 英文别名: 2-(4-(Dimesitylboryl)-phenyl)-quinoline；(4-quinolin-2-ylphenyl)-bis(2,4,6-trimethylphenyl)borane
• CAS: 332350-43-3
• 化学式: C₃₃H₃₂BN
• 分子量: 453.435
• InChiKey: CDHNVWLEUVVEFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-(di(mesityl)boryl)phenyl)quinoline 、 iridium(III) chloride trihydrate 以 乙二醇乙醚 、 水 为溶剂， 反应 24.0h， 生成 (Bpq)2Ir(μ-Cl)2Ir(Bpq)2
  参考文献：
  名称：

  Conjugated polymers with cationic iridium(iii) complexes in the side-chain for flash memory devices utilizing switchable through-space charge transfer

  摘要：

  设计和合成了侧链含有阳离子铱(III)配合物的聚咔唑和聚芴，两种聚合物均显示出导电开关行为，并成功实现了基于它们的非易失性闪存器件。在这些器件中，通过空间电荷转移状态的形成和解离，从共轭聚合物“海”到铱(III)配合物“岛”，受电压控制，负责导电开关行为和存储效应。器件具有低读取、写入和擦除电压以及高开/关电流比。两种开和关状态在−1.0 V读取电压下稳定高达107次读取周期。由于聚合物主链的不同化学结构，两种器件显示出不同的阈值电压。与聚芴类似物相比，聚咔唑衍生物具有更高的HOMO和LUMO能级。因此，基于聚咔唑衍生物的器件从关到开状态的阈值电压明显低于基于聚芴衍生物的器件，因为ITO阳极功函数与聚咔唑衍生物HOMO能级之间的能量屏障较低。同样，从开到关状态的阈值电压明显较高，因为从铝注入到聚咔唑衍生物LUMO的电子注入能量屏障略高于聚芴类似物。因此，通过修改聚合物的化学结构，可以合理地调节存储器件的阈值电压。

  DOI：

  10.1039/c2jm31963b
• 作为产物：
  描述：

  2-氨基苯甲醛 在 正丁基锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 19.0h， 生成 2-(4-(di(mesityl)boryl)phenyl)quinoline
  参考文献：
  名称：

  一种具有二齿配体的中性铱配合物及其制备 方法和应用

  摘要：

  本发明涉及一种具有二齿配体的中性铱配合物的其制备方法及其应用，属于光电功能有机材料技术领域。具体涉及一类具有二齿配体的铱配合物的制备方法有机电致发光器件和生物成像与标记中的应用。该类中性配合物以苯基喹啉衍生物为环金属配体，结构通式如下，化学式为[Ir(C^N)2(N^N)]。该材料合成步骤简单、条件温和，通过引入不同的主族元素改变不同的环金属配体来实现配合物的光物理性质的调节，并具有较高的量子效率，从而在有机光电功能材料领域有很大的应用前景。

  公开号：

  CN104086599B

文献信息

• Cationic Iridium(III) Complex Containing both Triarylboron and Carbazole Moieties as a Ratiometric Fluoride Probe That Utilizes a Switchable Triplet-Singlet Emission
  作者：Wen-Juan Xu、Shu-Juan Liu、Xin-Yan Zhao、Shi Sun、Shan Cheng、Ting-Chun Ma、Hui-Bin Sun、Qiang Zhao、Wei Huang

  DOI：10.1002/chem.201000362

  日期：2010.6.25

  This complex displayed highly efficient orange‐red phosphorescent emission with an emission peak of 583 nm and quantum efficiency of Φ=0.30 in dichloromethane at room temperature. The binding of fluoride ions to [Ir(Bpq)2(CzbpyCz)]PF6 can quench the phosphorescent emission from the IrIII complex and enhance the fluorescent emission from the N^N ligand, which corresponds to a visual change in the emission

  一种新的阳离子的Ir III配合物[Ir（BPQ）2（CzbpyCz）] PF 6（BPQ = 2- [4-（dimesitylboryl）苯基]喹啉，CzbpyCz = 5,5'-双（9-己基- 9 ħ咔合成了同时含有三芳基硼和咔唑基团的−3-yl）-2-2,2'-联吡啶）。[Ir（Bpq）2（CzbpyCz）] PF 6的激发态性质通过紫外/可见吸收和光致发光光谱以及分子轨道计算进行了研究。该复合物在室温下在二氯甲烷中显示出高效的橙红色磷光发射峰，发射峰为583 nm，量子效率为Φ = 0.30。氟离子与[Ir（Bpq）2（CzbpyCz）] PF的结合6可以淬灭Ir III配合物的磷光发射并增强N ^ N配体的荧光发射，这对应于从橙红色到蓝色的发射的视觉变化。因此，可以实现比色和比例氟化物感测。有趣的是，在可见光区域观察到了异常强烈的吸收带。和F的检测-离子也可以用可见光作为激发波长
• A near-infrared phosphorescent probe for F− based on a cationic iridium(III) complex with triarylboron moieties
  作者：WenJuan Xu、ShuJuan Liu、Qiang Zhao、TingChun Ma、Shi Sun、XinYan Zhao、Wei Huang

  DOI：10.1007/s11426-011-4359-y

  日期：2011.11

  In this work, a near-infrared (NIR) phosphorescent probe for F− based on a cationic Ir(III) complex [Ir(Bpq)2(quqo)]PF6 (1) with dimesitylboryl (Mes2B) groups on the cyclometalated C∧N ligands (Bpq) and 2-(quinolin-2-yl)quinoxaline (quqo) as N∧N ligand was designed and synthesized. The excited state properties of 1 were investigated in detail using molecular orbital calculations and experimental methods. Upon excitation, complex 1 shows NIR phosphorescent emission around 680 nm. Interestingly, the complex can be excited with long wavelength around 610 nm. Such long-wavelength excitation can reduce the background emission interference and improve the signal-to-noise ratio. Furthermore, the selective binding between boron atom and F− can give rise to the quenching of emission and realize the near-infrared phosphorescent sensing for F−. We wish that the results reported herein will be helpful for the further design of excellent near-infrared phosphorescent probes based on heavy-metal complexes.

  在这项工作中，设计并合成了一种基于阳离子铱(III)配合物[Ir(Bpq)2(quqo)]PF6 (1)的近红外(NIR)磷光探针，该配合物在环金属化C∧N配体(Bpq)上带有二甲苯基硼(Mes2B)基团，以2-(喹啉-2-基)喹喉(quqo)为N∧N配体。通过对1的激发态性质进行了分子轨道计算和实验方法的详细研究。在激发下，配合物1显示出约680 nm的近红外磷光发射。有趣的是，该配合物可用约610 nm的长波长激发。这种长波长激发可以减少背景发射干扰，并提高信噪比。此外，硼原子与F−的选择性结合可以导致发射淬灭，并实现F−的近红外磷光传感。我们希望这里报告的结果将有助于进一步设计基于重金属配合物的优秀近红外磷光探针。
• FRET-based probe for fluoride based on a phosphorescent iridium(iii) complex containing triarylboron groups
  作者：Wenjuan Xu、Shujuan Liu、Huibin Sun、Xinyan Zhao、Qiang Zhao、Shi Sun、Shan Cheng、Tingchun Ma、Lixia Zhou、Wei Huang

  DOI：10.1039/c1jm00071c

  日期：——

  An excellent F−probe (complex 1) based on carbazole-fluorene-carbazole (CzFCz) as a fluorescent donor and a cationic Ir(III) complex unit containing dimesitylboryl (Mes2B) groups as a phosphorescent acceptor has been designed and synthesized. Several reference compounds, such as complex 2 which is similar to complex 1 but without Mes2B groups, fluorescent donor CzFCz, and phosphorescent acceptors A1 and A2, were also synthesized in order to better understand the influence of Mes2B groups on the excited state properties and fluorescence resonance energy transfer (FRET) in this system. The introduction of Mes2B groups on the ligands of the Ir(III) complex unit can lead to a red-shifted and more intense absorption, facilitating efficient FRET from the fluorescent donor to the phosphorescent acceptor. Complex 1 displayed highly efficient orange-red phosphorescent emission with an emission peak at 584 nm in CH2Cl2 solution at room temperature. The emission wavelength of complex 1 in film is red-shifted to 600 nm with a shoulder at 650 nm, and its quantum efficiency in film was measured to be 0.15 under excitation at 450 nm. Utilizing the specific Lewis acid–base interactions between boron atom and F−, the binding of F− to complex 1 can change its excited state and suppress FRET, quenching the phosphorescent emission from the Ir(III) complex and enhancing the fluorescent emission from CzFCz. Thus, a visual change in the emission color from orange-red to blue was observed. Optical responses of complex 1 to F− revealed that it can be used as a highly selective, colorimetric and ratiometric optical probe for F− utilizing the switchable phosphorescence and fluorescence.

  基于咔唑-芴-咔唑(CzFCz)作为荧光供体和一个含有二甲基硼(Mes2B)基团的阳离子铱(III)配合物单元作为磷光受体，设计并合成了一种优秀的F-探针(复合物1)。为了更好地理解Mes2B基团对激发态性质和荧光共振能量转移(FRET)的影响，还合成了几种参考化合物，如与复合物1相似但不含有Mes2B基团的复合物2，荧光供体CzFCz以及磷光受体A1和A2。在铱(III)配合物单元的配体上引入Mes2B基团可以导致吸收红移并增强，从而促进从荧光供体到磷光受体的有效FRET。复合物1在室温CH2Cl2溶液中显示出高效的橙红色磷光发射，发射峰为584 nm。复合物1在薄膜中的发射波长红移至600 nm，并伴有650 nm的肩峰，在450 nm激发下测得其薄膜中的量子效率为0.15。利用硼原子和F-之间的特定Lewis酸碱相互作用，F-与复合物1的结合可以改变其激发态并抑制FRET，从而抑制铱(III)配合物的磷光发射并增强CzFCz的荧光发射。因此，观察到发射颜色的视觉变化，从橙红色变为蓝色。复合物1对F-的光学响应表明，它可以作为F-的高选择性、比色和比率光学探针，利用可切换的磷光和荧光。
• Highly Selective Phosphorescent Chemosensor for Fluoride Based on an Iridium(III) Complex Containing Arylborane Units
  作者：Qiang Zhao、Fuyou Li、Shujuan Liu、Mengxiao Yu、Zhiqiang Liu、Tao Yi、Chunhui Huang

  DOI：10.1021/ic800500c

  日期：2008.10.20

  A new phosphorescent iridium(III) complex [Ir(Bpq)(2)(bpy)]+PF6- based on cyclometalated ligands (Bpq) containing a dimesitylboryl group was synthesized and characterized by photophysical and electrochemical studies. The excited-state properties of Bpq and [Ir(Bpq)(2)(bpy)]+PF6- were investigated using molecular orbital calculations. Importantly, both Bpq and [Ir(Bpq)(2)(bpy)]+PF6- could be used as highly selective chemosensors for a fluoride anion (F-) detected by the naked eye, owing to the interaction of the dimesitylboryl group (BMes(2)) with F-. For the Bpq ligand, a red shift of the emission spectrum was observed upon the addition of F-, which could be attributed to an excited-state switch from a pi-pi* transition to a charge-transfer transition upon complexation with F-. The addition of F- to a solution of [Ir(Bpq)(2)(bpy)]+PF6- induced a change in the solution color from yellow to orange-red and phosphorescent quenching, indicating that [Ir(Bpq)(2)(bpy)]+PF6- could act as an excellent ON-OFF-type phosphorescent chemosensor for F-.