2,6-bis(N,N-dihexylamino)-4,8-diethynylbenzo[1,2-b:4,5-b’]difuran-3,7-dicarbonitrile | 1227073-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2,6-bis(N,N-dihexylamino)-4,8-diethynylbenzo[1,2-b:4,5-b’]difuran-3,7-dicarbonitrile
• 英文别名: 2,6-bis(dihexylamino)-4,8-diethynyl[1,2-b:4,5-b']difuran-3,7-dicarbonitrile；2,6-Bis(dihexylamino)-4,8-diethynylfuro[2,3-f][1]benzofuran-3,7-dicarbonitrile
• CAS: 1227073-82-6
• 化学式: C₄₀H₅₄N₄O₂
• 分子量: 622.894
• InChiKey: GXRSZVWUZRBHFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  46
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-碘吡啶 、 2,6-bis(N,N-dihexylamino)-4,8-diethynylbenzo[1,2-b:4,5-b’]difuran-3,7-dicarbonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以29%的产率得到2,6-Bis(dihexylamino)-4,8-bis(2-pyridin-4-ylethynyl)furo[2,3-f][1]benzofuran-3,7-dicarbonitrile
  参考文献：
  名称：

  Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended π-Conjugated Materials

  摘要：

  An efficient synthetic approach to construct a fully substituted benzo[1,2-b:4,5-b']difuran (BDF) 2a via base-catalyzed double annulations is presented. Compound 2a can readily undergo Suzuki, Heck, and Sonogashira coupling reactions to afford in good yields a manifold of extended pi-conjugated BDF derivatives, e.g., with pyridine termini (4-6) and with different spacers. These are highly luminescent materials that undergo two reversible one-electron oxidations. Remarkably, their photophysical and electrochemical properties can be largely tuned by methylation or protonation. Consequently, they can function as pH-dependent fluorescence switches. Finally, the observed electronic properties are explained on the basis of density functional theory.

  DOI：

  10.1021/jo100323s
• 作为产物：
  描述：

  2,6-Bis(dihexylamino)-4,8-bis(2-trimethylsilylethynyl)furo[2,3-f][1]benzofuran-3,7-dicarbonitrile 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以64%的产率得到2,6-bis(N,N-dihexylamino)-4,8-diethynylbenzo[1,2-b:4,5-b’]difuran-3,7-dicarbonitrile
  参考文献：
  名称：

  Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended π-Conjugated Materials

  摘要：

  An efficient synthetic approach to construct a fully substituted benzo[1,2-b:4,5-b']difuran (BDF) 2a via base-catalyzed double annulations is presented. Compound 2a can readily undergo Suzuki, Heck, and Sonogashira coupling reactions to afford in good yields a manifold of extended pi-conjugated BDF derivatives, e.g., with pyridine termini (4-6) and with different spacers. These are highly luminescent materials that undergo two reversible one-electron oxidations. Remarkably, their photophysical and electrochemical properties can be largely tuned by methylation or protonation. Consequently, they can function as pH-dependent fluorescence switches. Finally, the observed electronic properties are explained on the basis of density functional theory.

  DOI：

  10.1021/jo100323s

文献信息

• Synthesis and Redox and Photophysical Properties of Benzodifuran-Spiropyran Ensembles
  作者：Hui Li、Jie Ding、Songjie Chen、Christoph Beyer、Shi-Xia Liu、Hans-Achim Wagenknecht、Andreas Hauser、Silvio Decurtins

  DOI：10.1002/chem.201204043

  日期：2013.5.10

  (SP) systems and their BDF reference compounds were obtained in good yields through Huisgen–Meldal–Sharpless “click” chemistry and then subjected to investigation of their electrochemical and photophysical properties. In both SP and merocyanine (MC) forms of the coupled molecules, the BDF‐based emission is quenched to around 1 % of the quantum yield of emission from the BDF reference compounds. Based on

  通过Huisgen-Meldal-Sharpless“点击”化学法以高收率获得了两个苯并二呋喃（BDF）偶联的螺吡喃（SP）系统及其BDF参考化合物，然后对其电化学和光物理性质进行了研究。在SP和花青（MC）耦合分子形式中，基于BDF的发射被淬灭至BDF参考化合物发射的量子发射产率的1％左右。根据电化学数据，这种淬灭归因于氧化电子转移淬灭。在366 nm处进行辐照会导致BDF偶联SP化合物和SP参考化合物的MC形式开环，其量子效率约为50％。热环闭合的速率常数约为3.4×10 -3  s -1。但是，在光平稳状态下，偶联分子的MC分数显着低于参比SP化合物的MC分数，这归因于观察到的辐照后闭环反应的加速。由于在366 nm处进行辐照同样会激发偶联化合物中BDF单元的更高能跃迁，开环反应相对于SP参比会加速，从而导致光固定态下MC分数降低。这些与BDF偶联的SP化合物的可逆光致变色性使其在分子开关领域很有前途。
• Probing Charge Transfer in Benzodifuran-C₆₀Dumbbell-Type Electron Donor-Acceptor Conjugates: Ground- and Excited-State Assays
  作者：Hui Li、Christina Schubert、Pavlo O. Dral、Rubén D. Costa、Andrea La Rosa、Jürg Thüring、Shi-Xia Liu、Chenyi Yi、Salvatore Filippone、Nazario Martín、Silvio Decurtins、Timothy Clark、Dirk M. Guldi

  DOI：10.1002/cphc.201300378

  日期：2013.9.16

  Rigid electron donor–acceptor conjugates (1–3) that combine π‐extended benzodifurans as electron donors and C60 molecules as electron acceptors with different linkers have been synthesized and investigated with respect to intramolecular charge‐transfer events. Electrochemistry, fluorescence, and transient absorption measurements revealed tunable and structure‐dependent charge‐transfer processes in

  刚性电子供体-受体偶联物（1 - 3），其结合π扩展苯并二呋喃作为电子供体和C 60个分子为具有不同接头的电子受体已被合成，并且相对于分子内的电荷转移事件的影响。电化学，荧光和瞬态吸收测量揭示了在基态和激发态下可调谐的和依赖结构的电荷转移过程。我们的实验结果得到密度泛函理论计算的支持。
• A terpy-functionalized benzodifuran-based fluorescent probe for in vitro monitoring cellular Zn(II) uptake
  作者：Songjie Chen、Xiao Huang、Silvio Decurtins、Christiane Albrecht、Shi-Xia Liu

  DOI：10.1016/j.poly.2017.06.037

  日期：2017.9

  High interest in the detection and quantification of (elevated) intracellular zinc levels in tumor cells has been aroused due to the crucial physiological roles and the pathophysiological implications of zinc. Despite their diverse applications, benzo[1,2-b:4,5-b']difuran (BDF) derivatives as a fluorescent Zn(II) probe in living cells have not been reported. By careful chemical design of molecular components, we prepared and fully characterized a new amphiphilic BDF-based fluorophore. A series of experiments were carried out to test the cytotoxicity and cellular uptake behavior in human cancer derived HeLa cells. The ligand fluorescence is strongly quenched upon the addition of Zn(II) ions. The high cell membrane permeability, low cytotoxicity and significant fluorescence quenching behavior render this ligand very promising for in vitro detection of Zn(II) ions in biological systems. (C) 2017 Elsevier Ltd. All rights reserved.
• Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended π-Conjugated Materials
  作者：Chenyi Yi、Carmen Blum、Mario Lehmann、Stephan Keller、Shi-Xia Liu、Gabriela Frei、Antonia Neels、Jürg Hauser、Stefan Schürch、Silvio Decurtins

  DOI：10.1021/jo100323s

  日期：2010.5.21

  An efficient synthetic approach to construct a fully substituted benzo[1,2-b:4,5-b']difuran (BDF) 2a via base-catalyzed double annulations is presented. Compound 2a can readily undergo Suzuki, Heck, and Sonogashira coupling reactions to afford in good yields a manifold of extended pi-conjugated BDF derivatives, e.g., with pyridine termini (4-6) and with different spacers. These are highly luminescent materials that undergo two reversible one-electron oxidations. Remarkably, their photophysical and electrochemical properties can be largely tuned by methylation or protonation. Consequently, they can function as pH-dependent fluorescence switches. Finally, the observed electronic properties are explained on the basis of density functional theory.