4-[8-(4-Formylphenyl)octa-1,3,5,7-tetraynyl]benzaldehyde | 127653-18-3

• 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: 4-[8-(4-Formylphenyl)octa-1,3,5,7-tetraynyl]benzaldehyde
• CAS: 127653-18-3
• 化学式: C₂₂H₁₀O₂
• 分子量: 306.32
• InChiKey: XIIVWCFAQVVWEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[8-(4-Formylphenyl)octa-1,3,5,7-tetraynyl]benzaldehyde 在 氢溴酸 、 氧气 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 48.17h， 生成 1,8-bis(4-(13,17-dibutyl-2,8-diethyl-3,7,12,18-tetramethylporphyrin-5-yl)phenyl)octa-1,3,5,7-tetrayne
  参考文献：
  名称：

  Synthesis and Characterization of Polyyne Porphyrins

  摘要：

  一系列共轭的聚炔卟啉被制备，其中两个卟啉大环通过芳香环连接在二芳聚炔的两端，并对它们的光谱特性进行了研究。包含芳基和共轭三键系统的二芳聚炔具有刚性和线性结构，两个卟啉被固定在确定的几何形状和距离上。在它们的吸收光谱中，卟啉的索雷特带根据它们的边对边或面对面取向表现出红移或蓝移。

  DOI：

  10.1246/bcsj.63.170
• 作为产物：
  描述：

  1-Buta-1,3-diynyl-4-methoxymethoxymethyl-benzene 在 盐酸 、 manganese(IV) oxide 、 copper diacetate 作用下， 以 四氢呋喃 、 吡啶 、 丙酮 为溶剂， 反应 2.0h， 生成 4-[8-(4-Formylphenyl)octa-1,3,5,7-tetraynyl]benzaldehyde
  参考文献：
  名称：

  Synthesis and Spectroscopic Investigation of Directly Conjugated Polyyne Porphyrins

  摘要：

  研究人员制备了一系列共轭多炔卟啉，其中卟啉大环通过芳香环直接与二元多炔的一端相连，并研究了它们的光谱行为。由芳基和共轭三键系统组成的二芳基多炔具有刚性和线性结构，两个发色团保持固定的几何形状和确定的距离。这些化合物的紫外-可见吸收光谱显示出很强的共轭作用，随着乙炔键数目的增加，光谱变宽，卟啉索雷特带略有红移。从它们的荧光激发光谱可以估算出从聚炔分子到卟啉分子的能量传递效率。无论它们的取代位置、几何形状和取向如何，能量传递效率几乎都是相同的。

  DOI：

  10.1246/bcsj.62.3498

文献信息

• A Convenient Synthesis of Polyyne-bridged Porphyrin Dimers
  作者：Shigeki Kawabata、Nobuhiro Tanabe、Atsuhiro OSUKA

  DOI：10.1246/cl.1994.1797

  日期：1994.10

  A convenient synthetic procedure of a series of polyyne-bridged porphyrin dimers from diphenylpolyyne dialdehydes is reported. Trichloroacetic acid catalyzed double condensation of diphenylpolyyne dialdehydes with bis(3-hexyl-4-methyl-2-pyrrolyl)methane and 3,5-di-tert-butylbenzaldehyde in acctonitrile-dichloromethane followed by p-chloranil oxidation gave a set of diporphyrin model compounds (Pn,

  报道了从二苯基聚炔二醛中合成一系列聚炔桥卟啉二聚体的简便方法。三氯乙酸催化二苯基聚炔二醛与双(3-己基-4-甲基-2-吡咯基)甲烷和3,5-二叔丁基苯甲醛在丙烯腈-二氯甲烷中的双缩合，然后对氯苯醌氧化得到一套双卟啉模型由共轭三键桥接的化合物 (Pn, n = 0–4)。
• Synthesis and Intramolecular Electron- and Energy-Transfer Reactions of Polyyne- or Polyene-Bridged Diporphyrins
  作者：Atsuhiro Osuka、Nobuhiro Tanabe、Shigeki Kawabata、Iwao Yamazaki、Yoshinobu Nishimura

  DOI：10.1021/jo00127a024

  日期：1995.11

  A series of geometrically restricted polyyne- or polyene-bridged diporphyrins 1-7 has been prepared by a convenient, one-pot, double porphyrin cyclization reaction in acceptable yields from the corresponding dialdehydes 1-7CHO. Polyene-bridged diporphyrins 8 and 9 were prepared by a double Horner-Emmons-Wadsworth reaction of formyl-substituted zinc-porphyrin monomer 12 with bis-phosphonate esters 13 and 14, respectively. The diporphyrins 1-9 were transformed into zinc-free-base and zinc-ferric hybrid diporphyrins. Photoinduced intramolecular electron transfer in the zinc-ferric hybrid diporphyrins as well as intramolecular excitation energy transfer in the zinc-free-base hybrid diporphyrins have been studied by picosecond time-resolved fluorescence spectroscopy. Rate constants through the polyene-bridges are larger than those through the polyyne-bridges in both reactions. The distance dependence of the electron-transfer rate was found to be quite small: the attenuation factors were determined to be 0.08 and 0.1 Angstrom(-1) for the polyene- and polyyne-bridged diporphyrins, respectively. The distance dependence of the energy-transfer rate was quite similar to that of the electron transfer and was explained better by the Dexter mechanism rather than by the Forster mechanism. These results clearly demonstrate that the linear pi-conjugated polyyne and polyene spacers enhance through-bond electronic coupling between the donor and acceptor.
• MARUYAMA, KAZUHIRO;KAWABATA, SHIGEKI, BULL. CHEM. SOC. JAP., 62,(1989) N1, C. 3498-3507
  作者：MARUYAMA, KAZUHIRO、KAWABATA, SHIGEKI

  DOI：——

  日期：——
• MARUYAMA, KAZUHIRO;KAWABATA, SHIGEKI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 170-175
  作者：MARUYAMA, KAZUHIRO、KAWABATA, SHIGEKI

  DOI：——

  日期：——
• Synthesis and Characterization of Polyyne Porphyrins
  作者：Kazuhiro Maruyama、Shigeki Kawabata

  DOI：10.1246/bcsj.63.170

  日期：1990.1

  A series of conjugated polyyne porphyrins, in which two porphyrin macrocycles are connected with both ends of diarylpolyyne through aromatic ring, has been prepared and their spectroscopic behaviors were investigated. Diarylpolyyne consisting of aryl group and conjugated triple bond system have rigid and linear structure, and the two porphyrins are held at a fixed geometry and a determined distance. In their absorption spectra, porphyrin Soret bands were red- or blue-shifted depending on their edge-to-edge or face-to-face orientation.

  一系列共轭的聚炔卟啉被制备，其中两个卟啉大环通过芳香环连接在二芳聚炔的两端，并对它们的光谱特性进行了研究。包含芳基和共轭三键系统的二芳聚炔具有刚性和线性结构，两个卟啉被固定在确定的几何形状和距离上。在它们的吸收光谱中，卟啉的索雷特带根据它们的边对边或面对面取向表现出红移或蓝移。