2-[4-[(E)-2-[5-[2-[9,9-dibutyl-7-[2-[5-[(E)-2-[4-[ethyl(2-hydroxyethyl)amino]phenyl]ethenyl]thiophen-2-yl]ethynyl]fluoren-2-yl]ethynyl]thiophen-2-yl]ethenyl]-N-ethylanilino]ethanol | 1312471-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-[4-[(E)-2-[5-[2-[9,9-dibutyl-7-[2-[5-[(E)-2-[4-[ethyl(2-hydroxyethyl)amino]phenyl]ethenyl]thiophen-2-yl]ethynyl]fluoren-2-yl]ethynyl]thiophen-2-yl]ethenyl]-N-ethylanilino]ethanol
• CAS: 1312471-95-6
• 化学式: C₅₇H₆₀N₂O₂S₂
• 分子量: 869.248
• InChiKey: HKQQQMRNQAADAM-RYQLWAFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.4
• 重原子数：
  63
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4'-(9,9-dibutyl-9H-fluoren-2,7-diyl)bis(2-methyl-3-butyn-2-ol) 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 potassium tert-butylate 、 三乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 32.5h， 生成 2-[4-[(E)-2-[5-[2-[9,9-dibutyl-7-[2-[5-[(E)-2-[4-[ethyl(2-hydroxyethyl)amino]phenyl]ethenyl]thiophen-2-yl]ethynyl]fluoren-2-yl]ethynyl]thiophen-2-yl]ethenyl]-N-ethylanilino]ethanol
  参考文献：
  名称：

  Banana-shaped biphotonic quadrupolar chromophores: from fluorophores to biphotonic photosensitizers

  摘要：

  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。

  DOI：

  10.1039/c1nj20073a

文献信息

• [EN] BIPHOTONIC PHOTOSENSITIZERS, NANOPARTICLES CONTAINING THE SAME AND THEIR USE AS DRUGS<br/>[FR] PHOTOSENSIBILISATEURS BIPHOTONIQUES, NANOPARTICULES LES CONTENANT ET LEUR UTILISATION COMME MÉDICAMENTS
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2011073054A1

  公开（公告）日：2011-06-23

  The invention relates to compounds of formula (I) : the groups A and B represent independently from each other -CH=CH-, or -C≡C-, the terms t, u, v, w represent, independently from each other, values ranging from 0 to 9, the groups Y1 and Y2 can represent independently from each other an alkyl group (linear, branched or substituted) carrying from 1 to 9 carbon atoms, the groups Z1, Z2, Z3, and Z4 can represent independently from each other a chemically reactive group W, such as OH, NH2, SH, the groups Z5 and Z6 represent independently from each other a hydrogen atom, silica nanoparticles functionalized by these compounds, and their use as drugs.

  该发明涉及式(I)的化合物：其中基团A和基团B分别独立地表示-CH=CH-或-C≡C-，术语t、u、v、w分别独立地表示从0到9的值，基团Y1和基团Y2可以独立地表示一个烷基基团（直链、支链或取代基）带有1到9个碳原子，基团Z1、Z2、Z3和Z4可以独立地表示化学反应性基团W，例如OH、NH2、SH，基团Z5和Z6可以独立地表示氢原子，以及这些化合物功能化的二氧化硅纳米颗粒及其作为药物的用途。
• BIPHOTONIC PHOTOSENSITIZERS, NANOPARTICLES CONTAINING THE SAME AND THEIR USE AS DRUGS
  申请人：Brevet David

  公开号：US20130065849A1

  公开（公告）日：2013-03-14

  The invention relates to compounds of formula (I) wherein the groups A and B represent independently from each other —CH═CH—, or —C≡C—, the terms t, u, v, w represent, independently from each other, values ranging from 0 to 9, the groups Y 1 and Y 2 can represent independently from each other an alkyl group (linear, branched or substituted) carrying from 1 to 9 carbon atoms, the groups Z 1 , Z 2 , Z 3 , and Z 4 can represent independently from each other a chemically reactive group W, such as OH, NH 2 , SH, the groups Z 5 and Z 6 represent independently from each other a hydrogen atom, silica nanoparticles functionalized by these compounds, and their use as drugs.

  本发明涉及公式(I)的化合物，其中A和B基团分别独立地表示—CH═CH—或—C≡C—，t、u、v和w术语分别独立地表示从0到9的值，Y1和Y2基团可以独立地表示带有1到9个碳原子的烷基基团（直链、支链或取代基），Z1、Z2、Z3和Z4基团可以独立地表示化学反应性基团W，例如OH、NH2、SH，Z5和Z6基团可以独立地表示氢原子，以及由这些化合物功能化的二氧化硅纳米颗粒和它们作为药物的用途。
• 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。