1,2-bis(4-bromophenyl)-1,2-diphenylethylene

• 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-bis(4-bromophenyl)-1,2-diphenylethylene
• 英文别名: 1,2-bis(4-bromophenyl)-1,2-diphenylethene；1,2-Di(4-bromophenyl)-1,2-diphenylethylene；1-bromo-4-[2-(4-bromophenyl)-1,2-diphenylethenyl]benzene
• 化学式: C₂₆H₁₈Br₂
• 分子量: 490.237
• InChiKey: BBSNJTOHVHUCRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-bis(4-bromophenyl)-1,2-diphenylethylene 在 哌啶 、 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴化三(三苯基磷)铜 、 三乙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 1,2-bis{4-[1-(6-phenoxyhexyl)-1,2,3-triazol-4-yl]phenyl}-1,2-diphenylethene
  参考文献：
  名称：

  Hyperbranched polytriazoles with high molecular compressibility: aggregation-induced emission and superamplified explosive detection

  摘要：

  具有春季类似架构的超分支聚合物由于聚合物球从溶液到聚合物的高压缩性而表现出聚合物诱导排放(AIE)的特征。

  DOI：

  10.1039/c0jm04100a
• 作为产物：
  描述：

  4-甲基二苯甲酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 10.0h， 生成 1,2-bis(4-bromophenyl)-1,2-diphenylethylene
  参考文献：
  名称：

  Ratiometric Fluorescent Biosensor for Hyaluronidase with Hyaluronan As Both Nanoparticle Scaffold and Substrate for Enzymatic Reaction

  摘要：

  Hyaluronidases (HAase) are involved in various physiological and pathological processes and have been reported as urinary marker for bladder cancer. In this study, a novel ratiometric fluorescent sensing system based on both aggregation-induced emission (AIE) and aggregation-induced quenching (ACQ) was developed to quantitatively assess hyaluronidase level. First, a tetraphenylethylene derivative with positive charges (TPE-2N(+), typical AIE molecule) at both ends and an anthracene derivative with positive charge at one end (AN-N(+), typical ACQ molecule) was synthesized. These two positively charged compounds were then mixed with a negatively charged hyaluronan (HA), which induced the aggregation of the compounds as well as the nanoparticles formation as a result of electrostatic complexation, with TPE-2N(+) acting as cross-linking agent. The aggregation also caused the efficient quenching of the emission of AN-N(+) due to ACQ effect, as well as the fluorescence enhancement of TPE-2N(+) due to AIE effect. In the presence of HAase, the enzymatic reaction led to the degradation of HA and triggered disassembly of the nanoparticles; as a result, the emission of AN-N(+) was restored and that of TPE-2N(+) was suppressed. This fluorescence variation affords the system a robust ratiometric biosensor for HAase, and the ratio of fluorescence intensity for AN-N(+) (I414) to that for TPE-2N(+) (I474) can be used as the sensing signal for detecting HAase activity. In this system, hyaluronan serves not only as the scaffold for nanoparticle formation but also as the substrate for enzymatic reaction. This assay system is operable in aqueous media with very low detection limit of 0.0017 U/mL and is capable of detecting HAase in biological fluids such as serum and urine. This strategy may provide a new and effective approach for developing other enzyme assays.

  DOI：

  10.1021/bm500890d

文献信息

• Synthesis and Structure of <i>meso</i> ‐Substituted Dibenzihomoporphyrins
  作者：Nitika Grover、Ganapathi Emandi、Brendan Twamley、Bhavya Khurana、Vincent Sol、Mathias O. Senge

  DOI：10.1002/ejoc.202001165

  日期：2020.11.8

  analyses established the non‐planar structure of these molecules, with the phenylene rings out of the mean plane, as defined by the dipyrromethene moiety and the two meso‐carbon atoms. Spectroscopic and structural investigations show that the macrocycles exhibit characteristics of both TPE or but‐2‐ene‐2,3‐diyldibenzene and dipyrromethene units indicating the non‐aromatic characteristics of the compounds

  通过二吡咯衍生物与芳醛的酸催化缩合，合成了台架稳定的介孔取代的二（p/m-苄基）高卟啉。在卟啉骨架中插入1,1,2,2-四苯基乙烯（TPE）或丁-2-烯-2,3-二基二苯单元导致二苯并卟啉的形成，融合了烃和卟啉的特征。单晶 X 射线分析确定了这些分子的非平面结构，亚苯基环位于平均平面外，由二吡咯亚甲基部分和两个中间碳原子定义。光谱和结构研究表明，大环表现出 TPE 或丁-2-烯-2,3-二苯和二吡咯亚甲基单元的特征，表明合成的化合物具有非芳族特征。此外，
• Targeted combinational therapy inducing mitochondrial dysfunction
  作者：Weon Sup Shin、Soon Ki Park、Peter Verwilst、Seyoung Koo、Joung Hae Lee、Sung-Gil Chi、Jong Seung Kim

  DOI：10.1039/c6cc08977a

  日期：——

  Mitochondria-directed GSH-activated release of a chlorambucil derivative and an AIE dye induces significantly increased mitochondrial dysfunction and apoptosis.

  线粒体定向GSH激活释放氯氨鲁胺衍生物和AIE染料显著增加线粒体功能障碍和细胞凋亡。
• 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。
• A new AIE multi-block polyurethane copolymer material for subcellular microfilament imaging in living cells
  作者：Yu-qing Niu、Tao He、Jun Song、Si-ping Chen、Xiang-yu Liu、Zhi-gang Chen、Ying-jie Yu、Shi-guo Chen

  DOI：10.1039/c7cc02555f

  日期：——

  A multi-block fluorescent amphiphilic polyurethane copolymer (TPE-PU), self-assembling into hairy, water-soluble micelles, is used as a subcellular microfilament probe in living cells.

  一种多段荧光性两性聚氨酯共聚物（TPE-PU），自组装成毛状、水溶性胶束，在活细胞中用作亚细胞微丝探针。