1,4-bis(2-iodophenyl)buta-1,3-diyne | 155587-93-2

• 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: 1,4-bis(2-iodophenyl)buta-1,3-diyne
• 英文别名: 1,4-bis(oiodophenyl)diacetylene；1,4-di-(o-iodophenyl)butadiyne；bis(2-iodophenyl)butadiyne；1-iodo-2-[4-(2-iodophenyl)buta-1,3-diynyl]benzene
• CAS: 155587-93-2
• 化学式: C₁₆H₈I₂
• 分子量: 454.049
• InChiKey: ZFOAMWHBZIGDJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,4-bis(2-iodophenyl)buta-1,3-diyne 在 potassium fluoride 、 copper(l) iodide 、 二(氰基苯)二氯化钯 、 水 、 三苯基膦 、 copper(l) chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 生成 1,2:7,8:13,14:19,20-tetrabenzocyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne
  参考文献：
  名称：

  Synthesis and crystal structure of 1,2:7,8 : 13,14:19,20-tetrabenzocyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne

  摘要：

  标题化合物是通过格拉塞偶联反应以较高产率合成的，并通过 X 射线晶体学和光谱学进行了表征。

  DOI：

  10.1039/c39940000243
• 作为产物：
  描述：

  1-乙炔基-2-碘苯 在 copper diacetate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 1,4-bis(2-iodophenyl)buta-1,3-diyne
  参考文献：
  名称：

  Synthesis and crystal structure of 1,2:7,8 : 13,14:19,20-tetrabenzocyclotetracosa-1,7,13,19-tetraene-3,5,9,11,15,17,21,23-octayne

  摘要：

  标题化合物是通过格拉塞偶联反应以较高产率合成的，并通过 X 射线晶体学和光谱学进行了表征。

  DOI：

  10.1039/c39940000243

文献信息

• [EN] GRAPHENE NANORIBBONS WITH CONTROLLED ZIG-ZAG EDGE AND COVE EDGE CONFIGURATION<br/>[FR] NANORUBANS EN GRAPHÈNE A BORDS CONTRÔLÉS DE TYPE ZIGZAG ET À GORGE
  申请人：BASF SE

  公开号：WO2015121785A1

  公开（公告）日：2015-08-20

  Provided are graphene nanoribbons with controlled zig-zag edge and cove edge configuration and methods for preparing such graphene nanoribbons. The nanoribbons are selected from the following formulae.

  提供了具有受控锯齿边缘和凹边缘配置的石墨烯纳米带，以及制备这种石墨烯纳米带的方法。这些纳米带可从以下公式中选择。
• Toward Cove-Edged Low Band Gap Graphene Nanoribbons
  作者：Junzhi Liu、Bo-Wei Li、Yuan-Zhi Tan、Angelos Giannakopoulos、Carlos Sanchez-Sanchez、David Beljonne、Pascal Ruffieux、Roman Fasel、Xinliang Feng、Klaus Müllen

  DOI：10.1021/jacs.5b03017

  日期：2015.5.13

  Graphene nanoribbons (GNRs), defined as nanometer-wide strips of graphene, have attracted increasing attention as promising candidates for next-generation semiconductors. Here, we demonstrate a bottom-up strategy toward novel low band gap GNRs (Eg = 1.70 eV) with a well-defined cove-type periphery both in solution and on a solid substrate surface with chrysene as the key monomer. Corresponding cyclized

  石墨烯纳米带 (GNR) 被定义为纳米宽的石墨烯条带，作为下一代半导体的有希望的候选者，已引起越来越多的关注。在这里，我们展示了一种自下而上的策略，用于新型低带隙 GNR（Eg = 1.70 eV），在溶液中和固体基底表面上均具有明确的凹形外围，以芴作为关键单体。由二聚体和四聚体组成的相应环化基于 chrysene 的低聚物通过 Ullmann 偶联获得，然后在溶液中进行氧化分子内环化脱氢，并通过表面合成获得更高的 GNR 同系物。由于内凹位置的两个 C-H 键之间的空间排斥，这些低聚物采用非平面结构。通过单晶 X 射线分析、紫外-可见吸收光谱、核磁共振光谱、和扫描隧道显微镜 (STM) 进行了描述。密度泛函理论 (DFT) 计算有助于解释。
• Synthesis and Photophysical Studies of Chiral Helical Macrocyclic Scaffolds via Coordination-Driven Self-Assembly of 1,8,9,16-Tetraethynyltetraphenylene. Formation of Monometallic Platinum(II) and Dimetallic Platinum(II)−Ruthenium(II) Complexes
  作者：Fang Lin、Hai-Yan Peng、Jing-Xing Chen、David T. W. Chik、Zongwei Cai、Keith M. C. Wong、Vivian W. W. Yam、Henry N. C. Wong

  DOI：10.1021/ja106599j

  日期：2010.11.24

  This paper is concerned with the synthesis and reactions of enantiopure 1,8,9,16-tetraethynyltetraphenylene (3). We obtained 3 in 34% yield through four steps starting from 1,8,9,16-tetrahydroxytetraphenylene (2a) via a functional group interconversion strategy. On the basis of this chiral "helical" building block, three rigid helical macrocycles 14, 15, and 22 were designed. Complexes 14 and 15 were constructed via coordination-driven self-assembly with platinum(II) complexes 8 and 9b, while 22 cannot be obtained successfully. Then macrocycle 28 was designed on the structural basis of 22 to which octyl chains were introduced, in the hope of improving the solubility of the complex. Macrocycle 28 was finally formed and was characterized by NMR spectroscopy, elemental analysis, and electrospray mass spectrometry. For the enantiopure 15 and 28, circular dichroism (CD) spectra also exhibited chiral properties. Complexes 27 aid 28 both exhibited an intense emission band at 621 nm in acetonitrile at 298 K upon excitation at lambda > 420 nm.
• Versatile Synthetic Route to and DSC Analysis of Dehydrobenzoannulenes:  Crystal Structure of a Heretofore Inaccessible [20]Annulene Derivative
  作者：Michael M. Haley、Michael L. Bell、Jamieson J. English、Charles A. Johnson、Timothy J. R. Weakley

  DOI：10.1021/ja964048h

  日期：1997.3.1
• A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes
  作者：Michael L Bell、Ryan C Chiechi、Charles A Johnson、David B Kimball、Adam J Matzger、W Brad Wan、Timothy J.R Weakley、Michael M Haley

  DOI：10.1016/s0040-4020(01)00229-0

  日期：2001.4

  This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant alpha,omega -polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents. (C) 2001 Elsevier Science Ltd. All rights reserved.