2-(4-(dimesitylboranyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1359970-39-0

• 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: 2-(4-(dimesitylboranyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(4-(dimesitylboryl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-bis(2,4,6-trimethylphenyl)borane
• CAS: 1359970-39-0
• 化学式: C₃₀H₃₈B₂O₂
• 分子量: 452.253
• InChiKey: UUMXEDUSERIOOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(dimesitylboranyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-[14-[4-bis(2,4,6-trimethylphenyl)boranylphenyl]-8,8,9,9,10,10-hexafluoro-1,2-dimethyl-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraen-4-yl]-N,N-bis(4-methoxyphenyl)aniline
  参考文献：
  名称：

  A Triarylamine–Triarylborane Dyad with a Photochromic Dithienylethene Bridge

  摘要：

  A molecular triad composed of a triarylamine donor, a triarylborane acceptor, and a photoisomerizable dithienylethene bridge has been synthesized and explored by cyclic voltammetry, UV-vis, and luminescence spectroscopy. The effects of irradiation with UV light and fluoride addition on the electrochemical and optical spectroscopic properties of the donor-bridge-acceptor molecule were investigated. Photoisomerization of the dithienylethene bridge affects the triarylboron reduction potential, but not the triarylamine oxidation potential. UV-vis experiments reveal that the association constant for fluoride binding at the triarylborane site is independent of the isomerization state of the bridge. Irradiation of a THF solution of our donor-bridge-acceptor molecule with UV light, followed by F- addition, leads to a different color of the sample than UV irradiation alone or F- addition alone.

  DOI：

  10.1021/jo301083a
• 作为产物：
  描述：

  二(三甲苯基)氟化硼 在 正丁基锂 、 bis(triphenylylphosphine)palladium(II) dichloride 、 potassium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 7.5h， 生成 2-(4-(dimesitylboranyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Tri-(2-picolyl)amine-modificated triarylborane: Synthesis, photophysical properties and distinguish for cyanide and fluoride anions in aqueous solution

  摘要：

  We designed and synthesized a tri-(2-picolyl) amine (TPA) functionalized triarylborane, 1-(6-(4-(dimesitylboryl)phenyl)pyridin-2-yl)-N,N-bis(pyridin-2-ylmethyl)methanamine (PB2). The photophysical properties of PB2 were thoroughly explored. Moreover, PB2 can capture CN- and F- in aqueous solution through strong chelation induced by the synergy of a boron atom andmetal ion gripped by TPA to display entirely different fluorogenic responses such as fluorescence enhancement for CN- and fluorescence quenching for F-. The results of TOF-MS-EI analysis and theoretical calculations indicate that the complexing of PB2 with CN- formed a 2-to-2 adduct with a stabilized configuration, resulting in strong emission. The complexing of PB2 with F- formed a 1-to-1 adduct with a loose configuration, resulting in weak emission. In pure water, the detection limit of PB2 for CN- is 0.79 mu M, and in H2O/THF (1:9 v/v) system, the detection limits of PB2 for CN- and F- can reach 0.39 and 2.12 mu M, respectively, indicating its potential application for effective detection and discrimination of CN- and F-. (c) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2019.03.116

文献信息

• Responsive organoboranes with dynamic conformation of octacyclophane-type scaffolds: synthesis, AIE and temperature-dependent dual emissions
  作者：Kai Zhang、Guangqian Ji、Niu Zhang、Nan Wang、Xiaodong Yin、Quansong Li、Pangkuan Chen

  DOI：10.1039/d1tc02713a

  日期：——

  hypsochromic shift in the relatively long-lived charge transfer emissions at elevated temperature. Meanwhile, AIE activity of M1 and M2 was demonstrated with highly enhanced emissions in aggregated states. The present findings could provide an important guidance for multifunctional molecular design of responsive materials based on conformationally dynamic building blocks.

  在合成有机材料领域，仍然迫切需要在多种应用中显示出巨大潜力的新型智能材料。我们在此描述了一种用于合成发光有机硼烷 ( M1、M2和M3 )的设计策略，其特征是中央八元八环支架，两端带有电子供体 (Ar 3 N) 和受体 (Ar 3 B)。在这些结构高度相似的结构中，三芳基胺 (Ar 3 N) 和三芳基硼烷 (Ar 3 B) 部分之间的分子内电荷转移 (ICT)通过简单地调整八环芳型间隔物的电子结构来调节。M1 ,M2和M3显示出不寻常的双重发射，具有对空气和温度非常敏感的局部激发 (LE) 和 CT 特征。有趣的是，在热刺激下观察到弯曲八环烷的动态构象转换，并通过瞬态吸收光谱研究了激发态动力学。这些有机硼烷显示出热响应发光，在高温下相对长寿命的电荷转移发射具有明显的低色移。同时，M1和M2 的AIE 活动被证明在聚合状态下排放量大大增加。本研究结果可为基于构象动态构建块的响应材料的多功能分子设计提供重要指导。
• Di-(2-picolyl)-<i>N-</i> (2-quinolinylmethyl)amine-Functionalized Triarylboron: Lewis Acidity Enhancement and Fluorogenic Discrimination Between Fluoride and Cyanide in Aqueous Solution
  作者：Mao-Sen Yuan、Xianchao Du、Zhiqiang Liu、Tianbao Li、Wenji Wang、Eric V. Anslyn、Jinyi Wang

  DOI：10.1002/chem.201800884

  日期：2018.7.2

  Triarylboron‐based Lewis acids as fluoride sensors face a stimulating academic challenge because of the high hydration enthalpy of fluoride, and are usually influenced by a competing response for cyanide ion. Herein, we present a new triarylborane functionalized by a metal‐ion ligand, di‐(2‐picolyl)‐N‐(2‐quinolinylmethyl)amine, with subsequent metalation. In aqueous solution, this triarylborane (QB)

  基于三芳基硼的路易斯酸作为氟化物传感器，由于氟化物的高水化焓而面临着令人兴奋的学术挑战，通常受氰化物离子竞争性竞争的影响。在这里，我们介绍了一种新的由金属离子配体二（2-吡啶甲基）-N-（2-喹啉基甲基）胺官能化的三芳基硼烷，并随后进行了金属化。在水溶液中，这种三芳基硼烷（QB）可以通过硼和金属离子协同作用引起的螯合作用捕获氟离子和氰离子。此外，该三芳基硼烷部分充当结合的荧光报告分子，可通过双通道荧光变化区分氟化物和氰化物阴离子。不同的螯合模型，该传感器对的F荧光反应-和CN -通过的2对2加合物为KCN和1对1为KF单晶结构验证。
• Synthesis, Characterization, and Photophysical Properties of Triptycene-Based Chiral Organoboranes
  作者：Songhe Zhang、Jin-Fa Chen、Guofei Hu、Niu Zhang、Nan Wang、Xiaodong Yin、Pangkuan Chen

  DOI：10.1021/acs.organomet.1c00447

  日期：2022.1.24

  Their chiral optical properties, including circular dichroism (CD) and circularly polarized luminescence (CPL), are further studied because of the inherent chirality of triptycene derivatives. This work may contribute to the development of new chiral luminescent materials based on the rigid, homoconjugated, and structurally unusual three-dimensional triptycene scaffolds.

  通过经典的 Buchwald 偶联和 Suzuki 偶联反应合成了用给电子咔唑和受电子三芳基硼烷功能化的手性发光三蝶烯（HC-BN和HC-BB ）。由于分子内电荷转移 (ICT) 特性，同时含有咔唑和三芳基硼烷的化合物HC-BN表现出显着的发射热变色位移。由于三蝶烯衍生物的固有手性，进一步研究了它们的手性光学性质，包括圆二色性 (CD) 和圆偏振发光 (CPL)。这项工作可能有助于开发基于刚性、同质共轭和结构不寻常的三维三蝶烯支架的新型手性发光材料。
• Molecular design to enhance binaphthyl-based chiroptics using organoboron chemistry in isomeric chiral scaffolds
  作者：Kai Zhang、Jingyi Zhao、Niu Zhang、Jin-Fa Chen、Nan Wang、Xiaodong Yin、Xiaoyan Zheng、Pangkuan Chen

  DOI：10.1039/d1tc05329a

  日期：——

  Access to high-performance circularly polarized luminescence is highly desired in materials science but it hitherto remains a considerable challenge. We herein present a conceptually universal design strategy to improve the chiral luminescent properties of a series of binaphthyl-based compounds (MeBTT, MeBTB, p-BTT, p-BTB, m-BTT and m-BTB). The binaphthyl skeleton in all cases was π-functionalized

  材料科学非常需要获得高性能圆偏振发光，但迄今为止它仍然是一个相当大的挑战。我们在此提出了一种概念上通用的设计策略，以改善一系列基于联萘的化合物（MeBTT、MeBTB、p -BTT、p -BTB、m -BTT和m -BTB）的手性发光特性。在所有情况下，联萘骨架都被电子供体（Ar 3 N）或受体（Ar 3B），并系统地研究了分子结构与其光物理特性的相关性。它们在量子效率（ Φ PL,DCM）高达 100% 的溶液和固体（Φ PL,solid = 21-59%）中均表现出强光致发光。通过手性 HPLC 将p -BTT、p -BTB、m -BTT和m -BTB与螺旋环状结构的联萘实现了对映异构体的光学拆分。我们进一步揭示了空间上更受约束的m -BTT和m -BTB相对于异构体p -BTT和p -BTB在圆偏振发光 (CPL) 中表现出优异的手性特性，这从溶液中的发光不对称因子 (| g lum
• Diazocine Derivatives: A Family of Azobenzenes for Photochromism with Highly Enhanced Turn-On Fluorescence
  作者：Qian Zhu、Suning Wang、Pangkuan Chen

  DOI：10.1021/acs.orglett.9b01215

  日期：2019.6.7

  π-Conjugated azobenzene derivatives were reported to couple azo moieties with aryl fluorophore. Using the photochemistry of the C2-bridged azobenzene, we have accomplished two diazocine-based photoswitching molecules (cAz1 and cAz2). In addition to remarkable photochromic properties, they show a turn-on fluorescence, and the emission was highly enhanced with quantum efficiency increasing up to 0.22 for

  据报道，π共轭的偶氮苯衍生物使偶氮部分与芳基荧光团偶联。使用C 2桥连的偶氮苯的光化学，我们完成了两个基于重氮基的光开关分子（cAz1和cAz2）。除了显着的光致变色特性外，它们还显示出开启的荧光，并且随着cAz1的量子效率提高到0.22，发光得到了极大的增强。辐射持续存在，只能通过热停用将其关闭。与线性类似物（Az1 – Az4）。这项工作可以为使用光开关系统的高级发光材料提供新的支架。