B(subphthalocyanine)(ethynylphenyliodo) | 1101245-92-4

• 英文名称: B(subphthalocyanine)(ethynylphenyliodo)
• CAS: 1101245-92-4
• 化学式: C₃₂H₁₆BIN₆
• 分子量: 622.235
• InChiKey: MDEBDXGSGHVFBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  B(subphthalocyanine)(ethynylphenyliodo) 、 2-(4-ethynylphenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 三苯胂 、 N,N-二异丙基乙胺 作用下， 以58 %的产率得到
  参考文献：
  名称：

  具有寡聚（亚苯基乙炔基）桥接单元的二氢甘菊环-硼亚酞菁缀合物：光可切换荧光团

  摘要：

  制备了二氢甘菊环-硼亚酞菁 (DHA-BsubPc) 缀合物，并研究了 BsubPc（不带或带外围氟取代基）对 DHA 光异构化为乙烯基七富烯 (VHF) 的能力的影响，反之亦然BsubPc 荧光上的 DHA 和 VHF（开/关）。

  DOI：

  10.1002/ejoc.202300284
• 作为产物：
  描述：

  subphthalocyanine 、 (4-碘苯基乙炔)三甲基硅烷 在 aluminum (III) chloride 作用下， 以 邻二氯苯 为溶剂， 反应 16.0h， 以89%的产率得到B(subphthalocyanine)(ethynylphenyliodo)
  参考文献：
  名称：

  Aluminum Chloride Mediated Alkynylation of Boron Subphthalocyanine Chloride Using Trimethylsilyl-Capped Acetylenes

  摘要：

  A mild and versatile procedure is presented for functionalization of boron chloride subphthalocyanine at the axial boron position with trimethylsilyl-protected alkyne nucleophiles in the presence of aluminum chloride. The method allows a large variety of substituents on the alkyne units, including electron-donating/withdrawing aryl groups, silyl-protected alkynyl groups, as well as ferrocenyl and azulenyl groups. In addition, ferrocene itself reacts smoothly under these conditions allowing for directly anchoring it to the boron of the subphthalocyanine.

  DOI：

  10.1021/acs.joc.5b02719

文献信息

• Exploring the Synthesis and Electronic Properties of Axially Substituted Boron Subphthalocyanines with Carbon‐Based Functional Groups
  作者：Esmeralda Bukuroshi、Anne Ugleholdt Petersen、Line Broløs、Timothy P. Bender、Mogens Brøndsted Nielsen

  DOI：10.1002/ejic.202000525

  日期：2020.9.30

  properties of boron subphthalocyanines (BsubPcs), it is the intent of this study to further expand a matrix of BsubPcs to correlate structural changes to properties. Here, we have adapted previous synthetic methodologies for accessing axially substituted BsubPcs with a variety of alkyne substituents along with incorporating various peripheral halogens. While axial substitution of BsubPcs results in

  已知周围的氟化和氯化作用会显着影响硼亚酞菁硼（BsubPcs）的溶解度，荧光量子产率和氧化还原特性，因此本研究的目的是进一步扩展BsubPcs的基质以使结构变化与性能相关。在这里，我们已经调整了以前的合成方法，以获取带有各种炔烃取代基的轴向取代的BsubPcs以及掺入各种外围卤素。虽然BsubPcs的轴向取代导致最长波长吸收的位移最小，但相对荧光量子产率却随轴向碳-碳三键数量的增加而降低。循环伏安法研究表明，每个额外的碳-碳三键，BsubPcs都可以更轻松地形成自由基阴离子，从一键到两个三键时发生的变化最大。同样，还原分布受外围卤化以及轴向芳基乙炔基自由基稳定能力的影响。总之，基于轴向炔烃的取代基对BsubPcs的特性有影响。
• Electronic Energy Transfer in Molecular Dyads Built Around Boron-Ethyne-Substituted Subphthalocyanines
  作者：Raymond Ziessel、Gilles Ulrich、Kristopher J. Elliott、Anthony Harriman

  DOI：10.1002/chem.200900394

  日期：2009.5.11

  approach, which leads to the formation of a stable BC≡C linkage, is demonstrated by the isolation of two shape‐persistent, photo‐active molecular‐scale dyads, each capable of multiple energy‐transfer steps (see scheme, S=singlet energy transfer; T=triplet energy transfer).

  已经设计了一种狡猾的策略，用于在中心硼原子处官能化和溶解亚酞菁，从而使固有的光物理性质保持完整。该方法可导致形成稳定的B scale C linkageC键，这是通过隔离两个形状持久的光敏分子尺度二元组来证明的，每个二元组都可以执行多个能量转移步骤（请参阅方案S =单重能量传递； T =三重能量传递）。
• Facile Synthesis of Highly Fluorescent <i>Boranil</i> Complexes
  作者：Denis Frath、Sébastien Azizi、Gilles Ulrich、Pascal Retailleau、Raymond Ziessel

  DOI：10.1021/ol2011665

  日期：2011.7.1

  Complexation of a large variety of Anils (aniline-imines) with boron(III) precursors provides stable Boranils, some of which have been structurally characterized. Analysis of their optical properties reveals that the fluorescence stems from an intraligand charge transfer (ILCT) state with the best quantum yields reaching 90%. Chemistry on the Boranils allows grafting of photoactive modules acting as energy antennae for borondipyrromethene (Bodipy) and subphtalocyanine (SubPc) fluorophores.
• Ethynyl-Boron Subphthalocyanines Displaying Efficient Cascade Energy Transfer and Large Stokes Shifts
  作者：Franck Camerel、Gilles Ulrich、Pascal Retailleau、Raymond Ziessel

  DOI：10.1002/anie.200803131

  日期：2008.11.3