4,4'-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bisbenzaldehyde | 1334406-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4,4'-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bisbenzaldehyde
• CAS: 1334406-27-7
• 化学式: C₃₉H₃₄O₂
• 分子量: 534.698
• InChiKey: ATKUKGXHWYJKIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.76
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三(2-氨基乙基)胺 、 4,4'-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bisbenzaldehyde 以 氘代氯仿 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Controllable Self-Assembly of Pills and Cages via Imine Condensation for Silver Cation Detection

  摘要：

  By condensing a trisamino linker with one of the two analogous bisaldehyde ligands, pills and tetrahedrons could be self-assembled. The self-assembled preference could be controlled by tuning the reaction conditions, including the size of side chain, concentration, and temperature. Coordination of silver cation quenches the fluorescence of the fluorene moieties on the pill, opening up opportunities for Ag+ cation detection.

  DOI：

  10.1021/acs.orglett.8b03174
• 作为产物：
  描述：

  芴 在 copper(l) iodide 、 PdCl2(PPh3)2 、 硫酸 、 四丁基溴化铵 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 35.83h， 生成 4,4'-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bisbenzaldehyde
  参考文献：
  名称：

  pK_a tuning in quadrupolar-type two-photon ratiometric fluorescent membrane probes

  摘要：

  设计了两种比例双光子pH探针，结合了接近生理pH值和大的双光子吸收响应的pK_a值。它们能够高效地染色GUV和细胞膜。

  DOI：

  10.1039/c5cc04573h

文献信息

• Banana-shaped biphotonic quadrupolar chromophores: from fluorophores to biphotonic photosensitizers
  作者：Cédric Rouxel、Marina Charlot、Youssef Mir、Céline Frochot、Olivier Mongin、Mireille Blanchard-Desce

  DOI：10.1039/c1nj20073a

  日期：——

  This study aims at designing dual-role biphotonic chromophores that could be used for photodynamic therapy (PDT) while maintaining some fluorescence in order to locate them, thus allowing selective irradiation of cancer cells when combined with targeting. Quadrupolar two-photon absorbing fluorophores were synthesized from the symmetrical functionalization of a fluorene core bearing elongated conjugated rods made from arylene–vinylene or arylene–ethynylene building blocks in order to test modifications which could increase singlet oxygen production ability while retaining some fluorescence and high two-photon absorption (TPA) cross-sections in the biological spectral range of interest. All chromophores show a polar emissive excited state whose dipole moment is highly dependent on the nature of the conjugated linker. Interestingly, the largest TPA responses in the NIR region as well as singlet oxygen quantum yield are correlated with the smallest dipole moment of the emissive excited-state. The molecular optimization study led to a multifunctional biphotonic chromophore combining high TPA cross-sections in the whole spectral range of interest (700–900 nm), reasonable singlet oxygen production efficiency, significant remaining fluorescence, and alcohol end-groups for further covalent grafting. This compound offers thus interesting potentialities for highly selective spatially-resolved two-photon PDT by incorporation in nanostructures.

  本研究旨在设计具有双重功能的双光子染料，这些染料不仅可用于光动力疗法（PDT），同时保持一定的荧光性能以便于定位，从而在与靶向结合时可以选择性地照射癌细胞。我们通过对称功能化含芴核心，该核心带有由亚苯基-亚乙烯基或亚苯基-亚乙炔基构建的延长共轭杆，合成了四极性双光子吸收荧光剂，以测试能够增加单线态氧生成能力、同时保留一定荧光和高双光子吸收（TPA）截面在感兴趣的生物光谱范围内的改性。所有染料均显示出极性发射激发态，其偶极矩高度依赖于共轭连接基的性质。有趣的是，在近红外区域最大的TPA响应以及单线态氧量子产率与发射激发态的最小偶极矩相关。分子优化研究导致了一种多功能双光子染料的合成，该染料在整个感兴趣的光谱范围（700-900 nm）内结合了高TPA截面、合理的单线态氧生成效率、显著的剩余荧光和可用于进一步共价接枝的醇端基。因此，该化合物通过纳入纳米结构，为高度选择性、空间分辨的双光子PDT提供了有趣的潜在应用。