8-(6b,10b-dihydrobenzocyclobutacenaphthylene)carbaldehyde | 219833-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-(6b,10b-dihydrobenzocyclobutacenaphthylene)carbaldehyde
• 英文别名: Pentacyclo[8.7.1.02,9.03,8.014,18]octadeca-1(17),3(8),4,6,10,12,14(18),15-octaene-5-carbaldehyde
• CAS: 219833-91-7
• 化学式: C₁₉H₁₂O
• 分子量: 256.304
• InChiKey: GZGGZFQLIUGHHG-UHFFFAOYSA-N

物化性质

• 沸点：
  407.9±34.0 °C(predicted)
• 密度：
  1.328±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  吡咯 、 8-(6b,10b-dihydrobenzocyclobutacenaphthylene)carbaldehyde 在 丙酸 作用下， 反应 0.83h， 以23%的产率得到
  参考文献：
  名称：

  Synthesis and characterization of a new meso-tetra-dihydro benzocyclobutacenaphthylene free-base porphyrin

  摘要：

  合成了一种介-四-6b,10b-二氢苯并[j]环丁并[a]苊游离基卟啉，并将其光物理性质、光化学性质和电化学性质与游离基介-四苯基卟啉进行了比较。还测定了这两种化合物的前沿轨道和 HOMO-LUMO 能隙。结果表明，介-6b,10b-二氢苯并[j]环丁并[a]苊卟啉与四苯基卟啉具有相同的性质。

  DOI：

  10.1142/s1088424618500062
• 作为产物：
  描述：

  1-甲醛哌嗪 、 8-bromo-6b,10b-dihydrobenzocyclobutacenaphthylene 在 正丁基锂 作用下， 生成 8-(6b,10b-dihydrobenzocyclobutacenaphthylene)carbaldehyde
  参考文献：
  名称：

  Benzocyclobutenoacenaphthylene Stilbenes. 1. Synthesis and Thermal Properties

  摘要：

  In this paper the synthesis and characterization of a new class of molecules based an 6b,10b-dihydroobenzo[j]cyclobut[a]acenaphthylene (DBCA) with potentially interesting optical and electronic properties are described. The mentioned compounds contain one or two DBCA units linked via a double bond to an aromatic system. The synthesis of these compounds is mainly carried out by Heck and/or Wittig reactions. The introduction of DBCA units in molecules is interesting in two respects: (1) It will influence the electronic and optical properties of the compounds, and (2) it will induce dimerization (polymerization) because DBCA can, upon thermolysis or photolysis, be converted into a biradicaloid species ("pleiadene") which dimerizes. Thus suitable compounds could be used as monomers for photochemically or thermally induced polymerization.

  DOI：

  10.1021/jo981016z

文献信息

• Benzocyclobutenoacenaphthylene Stilbenes. 1. Synthesis and Thermal Properties
  作者：Petra Buchacher、Roger Helgeson、Fred Wudl

  DOI：10.1021/jo981016z

  日期：1998.12.1

  In this paper the synthesis and characterization of a new class of molecules based an 6b,10b-dihydroobenzo[j]cyclobut[a]acenaphthylene (DBCA) with potentially interesting optical and electronic properties are described. The mentioned compounds contain one or two DBCA units linked via a double bond to an aromatic system. The synthesis of these compounds is mainly carried out by Heck and/or Wittig reactions. The introduction of DBCA units in molecules is interesting in two respects: (1) It will influence the electronic and optical properties of the compounds, and (2) it will induce dimerization (polymerization) because DBCA can, upon thermolysis or photolysis, be converted into a biradicaloid species ("pleiadene") which dimerizes. Thus suitable compounds could be used as monomers for photochemically or thermally induced polymerization.
• Synthesis and characterization of a new <i>meso</i>-tetra-dihydro benzocyclobutacenaphthylene free-base porphyrin
  作者：Ümit İşci、Sevinc Zehra Topal、Emel Önal、İsmail Fidan、Savaş Berber、Vefa Ahsen、Concepción Parejo、Ángela Sastre-Santos、Fabienne Dumoulin

  DOI：10.1142/s1088424618500062

  日期：2018.1

  A meso-tetra-6b,10b-dihydrobenzo[j]cyclobut[a]acenaphthylene free-base porphyrin was synthesised and its photophysical, photochemical and electrochemical properties were compared with those of free-base meso-tetraphenylporphyrin. The frontier orbitals and the HOMO–LUMO energy gaps of both compounds were also determined. It was demonstrated that the meso6b,10b-Dihydrobenzo[j]cyclobut[a]acenaphthylene porphyrin retained the same properties as the tetraphenylporphyrin.

  合成了一种介-四-6b,10b-二氢苯并[j]环丁并[a]苊游离基卟啉，并将其光物理性质、光化学性质和电化学性质与游离基介-四苯基卟啉进行了比较。还测定了这两种化合物的前沿轨道和 HOMO-LUMO 能隙。结果表明，介-6b,10b-二氢苯并[j]环丁并[a]苊卟啉与四苯基卟啉具有相同的性质。