8-iodo-6b,10b-dihydrobenzocyclobutacenaphthylene | 219833-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-iodo-6b,10b-dihydrobenzocyclobutacenaphthylene
• 英文别名: 8-iodo-6b-10b-dihydrobenzocyclobutacenaphthylene；8-iodo-DBCA；8-Iodo-6b,10b-dihydrobenzo[3,4]cyclobuta[1,2-a]acenaphthylene；5-iodopentacyclo[8.7.1.02,9.03,8.014,18]octadeca-1(17),3(8),4,6,10,12,14(18),15-octaene
• CAS: 219833-92-8
• 化学式: C₁₈H₁₁I
• 分子量: 354.19
• InChiKey: JKFPYEGOQFMNLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

上下游信息

反应信息

• 作为反应物：
  描述：

  8-iodo-6b,10b-dihydrobenzocyclobutacenaphthylene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  Synthesis and optical properties of phthalocyanine-dihydrobenzocyclobutacenaphthylene systems

  摘要：

  我们合成了外围被完全共轭的 6b,10b-二氢苯并[j]环丁并[a]苊（DBCA）取代的四种新型锌酞菁（ZnPcs 1-4），并对其进行了化学表征。在 ( DBCA )4 ZnPc 1 和 t Bu 3( DBCA ) ZnPc 2 中，DBCA 单元直接连接到酞菁核心，而在 ( VDBCA )4 ZnPc 3 和 t Bu 3( VDBCA ) ZnPc 4 中，DCBA 单元通过乙烯基间隔物连接。我们描述了取代基对光学光谱、荧光寿命和量子产率的影响。

  DOI：

  10.1142/s1088424613500879
• 作为产物：
  描述：

  2-氨基-5-碘苯甲酸 、 苊烯 在 亚硝酸异戊酯 、 三氯乙酸 作用下， 生成 8-iodo-6b,10b-dihydrobenzocyclobutacenaphthylene
  参考文献：
  名称：

  Pleiadene Dimerization and Its Application to the Construction of Novel Carbon Networks

  摘要：

  The synthesis of the anti- and syn-pleiadene dimers 2 has been carried out in solution and in the solid state from (6b-10b-dihydrobenzo[j]cyclobut[a]acenaphthylene) (3). The structures of the anti- and syn-2 dimers were determined by X-ray crystallography and by NMR spectroscopy and mass spectrometry. An exhaustive thermal analysis of the two dimers has been carried out, establishing that the equilibrium for their interconversion occurs via pleiadene as an intermediate species. Vinyl-6b-10b-dihydrobenzo[j]cyclobut[a]acenaphthylene (5) has been synthesized and used as a pre-monomer for the preparation of poly(pleiadene) dimer through either thermal or photochemical polymerization.

  DOI：

  10.1002/(sici)1521-3765(19990104)5:1<289::aid-chem289>3.0.co;2-1

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.
• Pleiadene Dimerization and Its Application to the Construction of Novel Carbon Networks
  作者：Ángela Sastre、Gordana Srdanov、Fred Wudl

  DOI：10.1002/(sici)1521-3765(19990104)5:1<289::aid-chem289>3.0.co;2-1

  日期：1999.1.4

  The synthesis of the anti- and syn-pleiadene dimers 2 has been carried out in solution and in the solid state from (6b-10b-dihydrobenzo[j]cyclobut[a]acenaphthylene) (3). The structures of the anti- and syn-2 dimers were determined by X-ray crystallography and by NMR spectroscopy and mass spectrometry. An exhaustive thermal analysis of the two dimers has been carried out, establishing that the equilibrium for their interconversion occurs via pleiadene as an intermediate species. Vinyl-6b-10b-dihydrobenzo[j]cyclobut[a]acenaphthylene (5) has been synthesized and used as a pre-monomer for the preparation of poly(pleiadene) dimer through either thermal or photochemical polymerization.
• Synthesis and optical properties of phthalocyanine-dihydrobenzocyclobutacenaphthylene systems
  作者：Javier Ortiz、Concepción Parejo、Federico Payá、Fernando Fernández-Lázaro、Larry Lüer、Ángela Sastre-Santos

  DOI：10.1142/s1088424613500879

  日期：2013.10

  Four new zinc phthalocyanines (ZnPcs 1–4) peripherally substituted with fully conjugated 6b,10b-dihydrobenzo[j]cyclobut[a]acenaphthylene (DBCA) have been synthesized and chemically characterized. In ( DBCA )₄ ZnPc 1 and ^t Bu ₃( DBCA ) ZnPc 2 the DBCA units are directly connected to the phthalocyanine core, meanwhile in ( VDBCA )₄ ZnPc 3 and ^t Bu ₃( VDBCA ) ZnPc 4 DCBA units are connected through a vinyl spacer. We describe the effect of the substituents on optical spectra, fluorescence lifetimes and quantum yields.

  我们合成了外围被完全共轭的 6b,10b-二氢苯并[j]环丁并[a]苊（DBCA）取代的四种新型锌酞菁（ZnPcs 1-4），并对其进行了化学表征。在 ( DBCA )4 ZnPc 1 和 t Bu 3( DBCA ) ZnPc 2 中，DBCA 单元直接连接到酞菁核心，而在 ( VDBCA )4 ZnPc 3 和 t Bu 3( VDBCA ) ZnPc 4 中，DCBA 单元通过乙烯基间隔物连接。我们描述了取代基对光学光谱、荧光寿命和量子产率的影响。