(1,2-diphenylethene-1,2-diyl)bis(4,4'-phenylene)-1,1'-diboronic acid | 1054451-31-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1,2-diphenylethene-1,2-diyl)bis(4,4'-phenylene)-1,1'-diboronic acid
• 英文别名: 4,4'-(1,2-diphenylethene-1,2-diyl)bis(1,4-phenylene)diboronic acid；((1,2-diphenylethene-1,2-diyl)bis(1,4-phenylene))diboronic acid；4,4'-(1,2-diphenyl-1,2-ethenylene)diphenylboronic acid；4,4'-(1,2-diphenylvinyl)-1,2-di-(phenylboronic acid)；((1,2-Diphenylethene-1,2-diyl)bis(4,1-phenylene))diboronicacid；[4-[2-(4-boronophenyl)-1,2-diphenylethenyl]phenyl]boronic acid
• CAS: 1054451-31-8
• 化学式: C₂₆H₂₂B₂O₄
• 分子量: 420.08
• InChiKey: CFKHFTZRFSABDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  32
• 可旋转键数：
  6
• 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

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (1,2-diphenylethene-1,2-diyl)bis(4,4'-phenylene)-1,1'-diboronic acid 、 2-溴-9,9'-螺二芴 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 12.0h， 以45%的产率得到1,2-bis[4-(9,9'-spirobifluorene-7-yl)phenyl]-1,2-diphenylethene
  参考文献：
  名称：

  由四苯乙烯加螺二芴或9,9-二苯芴组成的压致变色发光和电致发光材料

  摘要：

  在这项工作中，合成并表征了由四苯乙烯加螺二芴或9,9-二苯芴组成的一系列发光剂。这些发光剂在溶液中微弱地发出荧光，而它们在聚集状态下是高发射性的，固体膜中的荧光量子产率高达99％，这证明了聚集诱导的发射特性。从发光剂的固体中观察到可逆的变色发光。通过研磨发光剂的原始粉末，很容易实现从蓝色（445 nm）到绿色（503 nm）的显着发射颜色变化。通过用二氯甲烷蒸气将磨碎的粉末发烟，可以恢复蓝色发射。制造了使用发光剂作为发光层的无掺杂电致发光器件，提供高达7.2 cd / A的高电流效率。

  DOI：

  10.1016/j.dyepig.2014.02.026
• 作为产物：
  描述：

  4-溴苯甲酰苯 在 正丁基锂 、 四氯化钛 、 锌 作用下， 生成 (1,2-diphenylethene-1,2-diyl)bis(4,4'-phenylene)-1,1'-diboronic acid
  参考文献：
  名称：

  由四苯乙烯加螺二芴或9,9-二苯芴组成的压致变色发光和电致发光材料

  摘要：

  在这项工作中，合成并表征了由四苯乙烯加螺二芴或9,9-二苯芴组成的一系列发光剂。这些发光剂在溶液中微弱地发出荧光，而它们在聚集状态下是高发射性的，固体膜中的荧光量子产率高达99％，这证明了聚集诱导的发射特性。从发光剂的固体中观察到可逆的变色发光。通过研磨发光剂的原始粉末，很容易实现从蓝色（445 nm）到绿色（503 nm）的显着发射颜色变化。通过用二氯甲烷蒸气将磨碎的粉末发烟，可以恢复蓝色发射。制造了使用发光剂作为发光层的无掺杂电致发光器件，提供高达7.2 cd / A的高电流效率。

  DOI：

  10.1016/j.dyepig.2014.02.026

文献信息

• Water-soluble AIE luminogens for monitoring and retardation of fibrillation of amyloid proteins
  申请人：THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US09279806B2

  公开（公告）日：2016-03-08

  Compounds that exhibit aggregation induced emission (AIE), and more particularly to water-soluble conjugated polyene compounds that exhibit aggregation induced emission. The conjugated polyene compounds can be used as bioprobes for DNA detection, G-quadruplex identification, and potassium-ion sensing. The polyenes also can be utilized as an external fluorescent marker to study conformational structures, to monitor folding processes of label-free oligonucleotides with G-rich strand sequences, and to visualize DNA bands in PAGE assay. The polyenes have applications in high-throughput anticancer drug screening and are useful for the development of efficient anti-cancer drugs. Furthermore, the present subject matter can also be used to monitor fibrillation of amyloid proteins and to facilitate the storage and delivery thereof.

  表现出聚集诱导发光（AIE）特性的化合物，更具体地说是表现出聚集诱导发光特性的水溶性共轭聚烯烃化合物。这些共轭聚烯烃化合物可用作DNA检测的生物探针、G-四链体识别和钾离子感知。这些聚烯烃还可用作外部荧光标记物，用于研究构象结构，监测不带标签的富含G链序列的寡核苷酸的折叠过程，并在PAGE分析中可视化DNA条带。这些聚烯烃在高通量抗癌药物筛选中具有应用，并有助于开发高效的抗癌药物。此外，目前的主题还可用于监测淀粉样蛋白的纤维化，并促进其存储和传递。
• Luminogenic materials constructed from tetraphenylethene building blocks: Synthesis, aggregation-induced emission, two-photon absorption, light refraction, and explosive detection
  作者：Rongrong Hu、Jose Luis Maldonado、Mario Rodriguez、Chunmei Deng、Cathy K. W. Jim、Jacky W. Y. Lam、Matthew M. F. Yuen、Gabriel Ramos-Ortiz、Ben Zhong Tang

  DOI：10.1039/c1jm13556b

  日期：——

  Luminogenic molecules [(TPE)3 (1), TPE-C = C-TPE-C = C-TPE (2), and TPE-C≡C-TPE-C≡C-TPE (3)] and their polymers P1–P3 are constructed from tetraphenylethene (TPE) building blocks in high yields by Suzuki, Witting, and Sonogashira coupling reactions. All the compounds are soluble and enjoy high thermal stability, losing little of their weights when they are heated to 290–528 °C under nitrogen or 288–436 °C in air. Analyses by UV spectroscopy and cyclic voltammetry as well as theoretical calculations show that the conjugation of the luminophores is in the order of 2 > 3 > 1, P2 > P3 > P1, and P1–P3 > 1–3. All the molecules and polymers are weakly emissive in solutions. They, however, become strong emitters in the aggregate state with fluorescence quantum yields up to 90%. Both 1–3 and P1–P3 exhibit the feature of aggregation-enhanced two-photon excited fluorescence. Large two-photon absorption cross sections (up to ∼900 GM) are observed in the nanoaggregates of the polymers. Thin solid films of the polymers show high refractive indices (RI = 1.7649 − 1.6873) in a wide wavelength region of 400–1700 nm, high modified Abbé numbers (vD′ up to 3436), and low optical dispersions (D′ down to 2.9 × 10−4). The light emissions of the polymers can be quenched exponentially by picric acid with large quenching constants, suggesting that they can be utilized as efficient chemosensors for explosive detection.

  发光分子[(TPE)3 (1)，TPE-C=C-TPE-C=C-TPE (2)和TPE-C≡C-TPE-C≡C-TPE (3)]及其聚合物P1–P3由四苯乙烯（TPE）单元以高产率通过铃木、维廷和园田耦合反应构建而成。所有化合物均可溶，并具有高热稳定性，在氮气下加热至290–528 °C或在空气中加热至288–436 °C时，仅损失少量重量。通过紫外光谱、循环伏安法以及理论计算的分析表明，发光单元的共轭程度顺序为2 > 3 > 1，P2 > P3 > P1，以及P1–P3 > 1–3。所有分子和聚合物在溶液中发射强度较弱。然而，它们在聚集态中变为强发射体，荧光量子产率可高达90%。1–3和P1–P3均表现出聚集增强的双光子激发荧光特征。在聚合物的纳米聚集体中观察到较大的双光子吸收截面（达约900 GM）。聚合物的薄固体薄膜在400–1700 nm的宽波长区域内显示出高折射率（RI = 1.7649 − 1.6873）、高修正阿贝数（vD′高达3436）和低光学色散（D′低至2.9 × 10−4）。聚合物的光发射可被硝基苯酸以指数方式淬灭，且淬灭常数较大，表明它们可以作为高效的化学传感器用于爆炸物检测。
• Specific Recognition of β-Cyclodextrin by a Tetraphenylethene Luminogen through a Cooperative Boronic Acid/Diol Interaction
  作者：Yi Liu、Anjun Qin、Xiujuan Chen、Xiao Yuan Shen、Li Tong、Rongrong Hu、Jing Zhi Sun、Ben Zhong Tang

  DOI：10.1002/chem.201102613

  日期：2011.12.23

  unexpected recognition of β‐cyclodextrin (CD) from α‐ and γ‐CDs was achieved. The emission from a diboronic acid‐containing tetraphenylethene (TPEDB) was amplified upon addition of β‐CD, whereas there was almost no response for α‐, and γ‐CDs. TPEDB is proposed to be anchored onto the wide rim of β‐CD through the alternative and conceptually new cooperative boronic acid/diol dynamic binding interaction, resulting

  意外地从α-和γ-CD中识别出β-环糊精（CD）。添加β-CD后，含二硼酸四苯乙烯（TPEDB）的发射被放大，而α-和γ-CD几乎没有响应。有人建议将TPEDB通过替代的概念上新的协作性硼酸/二醇动态结合相互作用固定在β-CD的宽边上，从而限制其苯环的分子内旋转（参见方案）。
• AGGREGATION-INDUCED EMISSION LUMINOGENS FOR METAL ION DETECTION
  申请人：TANG Benzhong

  公开号：US20130059392A1

  公开（公告）日：2013-03-07

  Pyridine-containing polyenes and their applications as metal ion sensors. These polyenes are practically nonluminescent in the solution state but become highly emissive as nanoparticle suspensions in aqueous solutions or thin films in the solid state, due to aggregation-induced emission (AIE). The nanoaggregates of these compounds can work as “turn-off” fluorescent chemosensors for metal ions and display different fluorescence responses to various metal ions. For example, a characteristic red shift in the emission spectra is observed with a terpyridine-containing luminogen in the presence of Zn 2+ . However, the terpyridine-containing luminogen displays a magenta color upon selectively binding with Fe 2+ . This allows easy identification of both Zn 2+ and Fe 2+ ions in aqueous media. The function of the polyenes can be easily tuned by altering the substituent groups. Due to their AIE properties, these polyenes can be used in aqueous solutions and in solid substrates for metal sensing.

  含吡啶基的聚烯烃及其作为金属离子传感器的应用。这些聚烯烃在溶液状态下几乎不发光，但当作为纳米颗粒悬浮液存在于水溶液中或以薄膜形式存在于固态中时，由于聚集诱导发光（AIE）而变得高度发光。这些化合物的纳米聚集体可以作为金属离子的“关闭”荧光化学传感器，并对各种金属离子显示不同的荧光响应。例如，在存在Zn2+时，富含三吡啶的发光剂的发射光谱中观察到特征性的红移。然而，当与Fe2+选择性结合时，富含三吡啶的发光剂显示品红色。这使得在水介质中轻松识别Zn2+和Fe2+离子成为可能。通过改变取代基，可以轻松调节聚烯烃的功能。由于其AIE特性，这些聚烯烃可用于水溶液和固体基质中的金属传感。
• Daylight-stimulated antibacterial activity for sustainable bacterial detection and inhibition
  作者：Yuanhao Wu、Qixian Chen、Qiaoying Li、Hongguang Lu、Xinshi Wu、Jianbiao Ma、Hui Gao

  DOI：10.1039/c6tb01629d

  日期：——

  Light-stimulated AIE-based nanocomplexes have been developed as convenient tools to accomplish the tasks of the detection and inhibition of bacteria.

  光刺激的AIE基纳米复合体已被开发为方便工具，用于实现检测和抑制细菌的任务。