4-(anthracen-9-ylethynyl)benzaldehyde | 190441-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-(anthracen-9-ylethynyl)benzaldehyde
• 英文别名: 4-[(Anthracen-9-yl)ethynyl]benzaldehyde；4-(2-anthracen-9-ylethynyl)benzaldehyde
• CAS: 190441-24-8
• 化学式: C₂₃H₁₄O
• 分子量: 306.364
• InChiKey: NWNZNBHYLLXGKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙酮 、 4-(anthracen-9-ylethynyl)benzaldehyde 在 L-脯氨酸 作用下， 反应 96.0h， 以81%的产率得到4-(4-(anthracen-9-ylethynyl)phenyl)-4-hydroxybutan-2-one
  参考文献：
  名称：

  Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO

  摘要：

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.007
• 作为产物：
  描述：

  4-三甲基硅乙炔基苯甲醛 在 甲醇 、 四(三苯基膦)钯 、 potassium carbonate 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 44.0h， 生成 4-(anthracen-9-ylethynyl)benzaldehyde
  参考文献：
  名称：

  Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO

  摘要：

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.007

文献信息

• Synthesis, Photophysical Properties, and Field-Effect Characteristics of (Ethynylphenyl)benzimidazole-Decorated Anthracene and Perylene Bisimide Derivatives
  作者：I-Lin Lee、Sie-Rong Li、Kuan-Fu Chen、Po-Jen Ku、Ashutosh S. Singh、Hui-Tung Kuo、Yuh-Sheng Wen、Chi-Wei Chu、Shih-Sheng Sun

  DOI：10.1002/ejoc.201200032

  日期：2012.5

  anthracene derivatives, but only weak emission was observed for perylene bisimide derivatives. The anthracene derivatives showed typical p-type semiconducting character, even when the derivatives were substituted with electron-withdrawing benzimidazole groups at the 9- and 10-positions, which apparently does not lower the LUMO levels to transform them into electron-transporting molecules. Perylene bisimide

  设计并制备了一系列具有吸电子苯并咪唑取代基的蒽和苝双酰亚胺衍生物。对这些新化合物的电化学和光物理特性以及场效应迁移率进行了详细研究。与母体化合物相比，吸电子苯并咪唑基团的引入降低了蒽和苝双酰亚胺衍生物中的 LUMO 水平。所有蒽衍生物均观察到强发射，但苝双酰亚胺衍生物仅观察到微弱发射。蒽衍生物显示出典型的 p 型半导体特性，即使这些衍生物在 9 位和 10 位被吸电子苯并咪唑基团取代，这显然不会降低 LUMO 能级以将它们转化为电子传输分子。苝双酰亚胺衍生物显示出典型的 n 通道半导体特性，具有低阈值电压和约 10 倍的电子迁移率。5.2 × 10–5 cm2 V–1 s–1。
• Synthesis and Photochemical Properties of Anthracene-Polyyne-Porphyrin Assemblies
  作者：Shigeki Kawabata、Iwao Yamazaki、Yoshinobu Nishimura

  DOI：10.1246/bcsj.70.1125

  日期：1997.5

  A series of anthrylpolyynes (α-anthryl-ω-(formylphenyl)polyynes) and anthrylpolyynylporphyrins (5-[(anthrylpolyynyl)phenyl]porphyrins) have been synthesized, and their photochemical properties and photoinitiated intramolecular excitation energy transfer from anthracene to porphyrin were studied by picosecond time-resolved fluorescence spectroscopy. Although anthrylpolyynes have strong fluorescence emission and fluorescence high quantum yield, anthrylpolyynylporphyrins, in which porphyrin links to the other side of polyyne, show only typical fluorescence emission of porphyrin and almost no fluorescence emission in the spectral region of anthrylpolyynes. The excitation of anthryl substituent brings about an increase in the fluorescence emission of porphyrin on the picosecond time scale. The mechanism of quantitative energy transfer from the anthryl moiety to the porphyrin is discussed on the basis of the photochemical properties of the component molecules.

  合成了一系列蒽基多炔(α-蒽基-ω-(甲酰基苯基)多炔)和蒽基多炔基卟啉(5-[(蒽基多炔基)苯基]卟啉)，并研究了它们的光化学性质和从蒽到卟啉的光引发分子内激发能量转移。皮秒时间分辨荧光光谱。尽管蒽基多炔具有较强的荧光发射和较高的荧光量子产率，但卟啉与多炔的另一侧连接的蒽基多炔基卟啉仅表现出卟啉的典型荧光发射，而在蒽基多炔的光谱区几乎不发射荧光。蒽基取代基的激发导致卟啉在皮秒时间尺度上的荧光发射增加。基于组成分子的光化学性质，讨论了从蒽基部分到卟啉的定量能量转移的机制。
• Phenylethynylanthracene based push–pull molecular systems: tuning the photophysics through <i>para</i>-substituents on the phenyl ring
  作者：Sonali Sahu、Venkatakrishnan Parthasarathy、Ashok Kumar Mishra

  DOI：10.1039/d2cp05074a

  日期：——

  is quenched drastically by either decreasing or increasing solvent polarity. Fluorescence anisotropy studies show very good sensitivity of these compounds towards microviscosity of their immediate molecular environment. A white light emitting (WLE) gel was prepared using 4-(anthracen-9-ylethynyl)benzonitrile (AnPCN) and 4-(anthracen-9-ylethynyl)-N,N-dimethylaniline (AnPNMe2) by taking polyvinyl alcohol

  有机推拉分子包含通过π 键连接的供体和受体部分，分子内电子电荷转移 (ICT) 可以通过 π 键发生在基态和激发态；赋予这些分子有趣的光物理特性。在这项工作中选择的分子是一些基本的苯基乙炔基蒽衍生物，以表明只要改变取代基，这类小分子就可以显示其光物理性质的显着变化。这些分子的发射特性和 ICT 能力在各种给电子和吸电子取代基方面进行了比较。取代基如氰基和甲氧基羰基不会引起任何 ICT 特性，而取代基如醛、N、N-二甲基氨基和硝基在这类分子中引起明显的 ICT 特性，它们的发射光谱几乎延伸到整个可见区域。比较ICT特性与电子密度差计算结果相关。计算研究表明，分子在基态和激发态下都是平面的；除了含硝基的分子，它在激发态下具有正交扭曲结构。该分子的发射特性导致其被归入一类硝基芳烃，其在中等极性溶剂中显示出最大发射强度，并且通过降低或增加溶剂极性显着淬灭发射。荧光各向异性研究表明这些化合物对其直接分子环境的微观粘度非常敏感。使用
• Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO
  作者：Nobuyuki Mase、Taishi Ando、Fumiya Shibagaki、Atsushi Sugita、Tetsuo Narumi、Mitsuo Toda、Naoharu Watanabe、Fujie Tanaka

  DOI：10.1016/j.tetlet.2014.02.007

  日期：2014.3

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.