4-(prop-2-yn-1-yloxy)benzylphthalimide | 1613586-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-(prop-2-yn-1-yloxy)benzylphthalimide
• 英文别名: N-(4-(2-propynyloxy)benzyl)phthalimide；4-prop-2-ynyloxybenzylphthalimide
• CAS: 1613586-56-3
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: PNGVLDOADGISAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(prop-2-yn-1-yloxy)benzylphthalimide 、 3,5-dibenzyloxyphenyl-1-methylene azide 在 溴化三(三苯基磷)铜 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以92%的产率得到2-(4-((1-(3,5-bis(benzyloxy)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)benzyl)isoindoline-1,3-dione
  参考文献：
  名称：

  White-Light-Emitting Edge-Functionalized Graphene Quantum Dots

  摘要：

  AbstractGraphene quantum dots (GQDs) have received considerable attention for their potential applications in the development of novel optoelectronic materials. In the generation of optoelectronic devices, the development of GQDs that are regulated in terms of their size and dimensions and are unoxidized at the sp2 surfaces is desired. GQDs functionalized with bulky Fréchet’s dendritic wedges at the GQD periphery were synthesized. The single‐layered, size‐regulated structures of the dendronized GQDs were revealed by atomic force microscopy. The edge‐functionalization of the GQDs led to white‐light emission, which is an uncommon feature.

  DOI：

  10.1002/anie.201311248
• 作为产物：
  描述：

  4-(2-丙炔氧基)苯甲腈 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 29.25h， 生成 4-(prop-2-yn-1-yloxy)benzylphthalimide
  参考文献：
  名称：

  White-Light-Emitting Edge-Functionalized Graphene Quantum Dots

  摘要：

  AbstractGraphene quantum dots (GQDs) have received considerable attention for their potential applications in the development of novel optoelectronic materials. In the generation of optoelectronic devices, the development of GQDs that are regulated in terms of their size and dimensions and are unoxidized at the sp2 surfaces is desired. GQDs functionalized with bulky Fréchet’s dendritic wedges at the GQD periphery were synthesized. The single‐layered, size‐regulated structures of the dendronized GQDs were revealed by atomic force microscopy. The edge‐functionalization of the GQDs led to white‐light emission, which is an uncommon feature.

  DOI：

  10.1002/anie.201311248

文献信息

• Chemical Functionalisation and Photoluminescence of Graphene Quantum Dots
  作者：Ryo Sekiya、Yuichiro Uemura、Hiroyoshi Naito、Kensuke Naka、Takeharu Haino

  DOI：10.1002/chem.201504963

  日期：2016.6.6

  GQD‐1–4 and on the five‐membered imide rings at the periphery, and this suggested that the functional groups distort the periphery by steric interactions between neighbouring functional groups. The HOMO–LUMO bandgaps of GQD‐1–4 were estimated to be approximately 2 eV, and their low‐lying LUMO levels (<−3.9 eV) were lower than that of phenyl‐C61‐butyric acid methyl ester, an n‐type organic semiconductor

  石墨烯量子点（GQD）的化学修饰会影响其物理和化学性质；因此，研究有机官能团对GQD的影响对于开发GQD-有机杂化材料非常重要。通过Cu I催化的GQD-的惠斯根环加成反应制备了三个具有第三代树枝状楔形（GQD- 2），长烷基链（GQD- 3）和多面体低聚倍半硅氧烷基团（GQD- 4）的外围功能化GQD。1与有机叠氮化物。循环伏安法表明还原发生在GQD- 1 – 4的表面上以及在外围的五元酰亚胺环上，这表明官能团通过相邻官能团之间的空间相互作用使外围扭曲。GQD-的HOMO-LUMO带隙1 - 4估计为大约2电子伏特，它们的低洼LUMO水平（<-3.9 eV）的均高于苯基-C的下部61 -丁酸甲酯，的n-型有机半导体。GQD- 1 – 4在有机溶剂中的溶解度取决于存在的官能团。官能团可能覆盖了GQD的表面和外围，因此增加了它们对溶剂的亲和力并避免了沉淀。与GQD- 2类似，两个GQD- 3GQD-
• A Supramolecular Polymer Network of Graphene Quantum Dots
  作者：Yuichiro Uemura、Kairi Yamato、Ryo Sekiya、Takeharu Haino

  DOI：10.1002/anie.201713299

  日期：2018.4.23

  Graphene quantum dot (GQD)–organic hybrid compounds (GQD‐2 b–e) were prepared by introducing 3,4,5‐tri(hexadecyloxy)benzyl groups (C16) and linear chains terminated with a 2‐ureido‐4‐[1H]‐pyrimidinone (UPy) moiety onto the periphery of GQD‐1. GQD‐2 b–e formed supramolecular assemblies through hydrogen bonding between the UPy units. GPC analysis showed that GQDs with high loadings of the UPy group formed

  石墨烯量子点（GQD）-有机杂化化合物（GQD- 2 b - e）通过引入3,4,5-三（十六烷氧基）苄基（C16）和以2-脲基-4-[[ 1H]-嘧啶酮（UPy）部分位于GQD- 1的外围。GQD- 2 b – e通过UPy单元之间的氢键形成超分子组装体。GPC分析表明，UPy基团的高负载GQD形成了较大的组装，这一趋势已通过DOSY和粘度测量得到了证实。AFM图像显示GQD- 2 e在云母上的聚合物网络结构具有平坦结构（高度约1.1 nm），但在GQD- 2 a中未观察到此类结构，仅包含C16组。GQD- 2 c和GQD- 2 d在正癸醇中形成有机凝胶，可以通过用乙二醇链（GQD- 3）取代UPy基团的烷基链来改变凝胶性质。因此，GQD可以通过适当的化学官能化用作超分子聚合物和有机胶凝剂的平台。