2-Cyclohexyl-6-hydrazinylbenzo[de]isoquinoline-1,3-dione | 27074-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-Cyclohexyl-6-hydrazinylbenzo[de]isoquinoline-1,3-dione
• 英文别名: 2-cyclohexyl-6-hydrazinylbenzo[de]isoquinoline-1,3-dione
• CAS: 27074-86-8
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: JOBMFRDIZZDBJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-（1,2,2-三苯基乙烯基）苯甲醛 、 2-Cyclohexyl-6-hydrazinylbenzo[de]isoquinoline-1,3-dione 在 哌啶 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 (Z)-2-cyclohexyl-6-(2-(4-(1,2,2-triphenylvinyl)benzylidene)hydrazineyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  基于萘二甲酰亚胺的Hy衍生物：合成，固态机械变色和稀溶液中对离子的响应

  摘要：

  显示出机械致变色发光（MCL）的分子有望用于传感和探针领域。我们报告了基于萘二甲酰亚胺的new衍生物NI‐TPE和NI‐3BA的设计和合成。两个luminogens是弱发射与小号Φ ˚F =分别为0.3％和0.5％无定形状态为强π-π堆积和分子间相互作用聚集时防止发光。相反，在结晶状态下，对两种衍生物的单晶分析表明，非辐射衰变被分子堆积模式和分子间相互作用所减少或抑制。荧光发射强度的增加，以小号Φ ˚F溶剂蒸发后的= 5.5％和6.0％是由于弱的π-π重叠和氢键（NH-⋅⋅⋅O，距离2.99Å），这有利于形成具有松散堆积的分子。同时，两种衍生物在晶格中采用的堆积模式被破坏，从而导致低的固态荧光量子产率和研磨时的红移在23–25 nm之间。所有这些因素导致两个导数显示出异常的“关闭” MCL现象。还证明了在稀溶液中荧光发射，其pH可逆性以及对氟离子和乙酸根离子的选择性响应高达91–93％。

  DOI：

  10.1002/cplu.202000764
• 作为产物：
  描述：

  环己胺 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-Cyclohexyl-6-hydrazinylbenzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Solvent Dependent Energy Transfer ofN-bridged Naphthalimide-Bisindolymaleimide Fluorescent Dyes

  摘要：

  Double build-in chromophores, naphthalimide (NIM) and bisindolymaleimide (BIM), were synthesized and characterized. Absorption and emission properties of double chromophores dye were fully investigated in various solvents. The priority of through bond energy transfer (TBET) to NTM or BIM is solvent dependent. There appears large different emission wavelength change in CHCl3 and DMF with alkyl attached to BIM. However, the product of cyclohexyl substitution leads to a different emission behavior, which is non-sensitivity to solvent polarity. Quantum chemical calculation for the molecular orbital reveals that intramolecular charge transfer (ICT) is the key factor for their different opto-electronic properties.

  DOI：

  10.1080/15421406.2013.844882

文献信息

• Solvent Dependent Energy Transfer of<i>N</i>-bridged Naphthalimide-Bisindolymaleimide Fluorescent Dyes
  作者：Xiaochuan Li、Kaijuan Zhu、Yajuan Li、Hyungjoo Kim、Young-A Son

  DOI：10.1080/15421406.2013.844882

  日期：2013.1

  Double build-in chromophores, naphthalimide (NIM) and bisindolymaleimide (BIM), were synthesized and characterized. Absorption and emission properties of double chromophores dye were fully investigated in various solvents. The priority of through bond energy transfer (TBET) to NTM or BIM is solvent dependent. There appears large different emission wavelength change in CHCl3 and DMF with alkyl attached to BIM. However, the product of cyclohexyl substitution leads to a different emission behavior, which is non-sensitivity to solvent polarity. Quantum chemical calculation for the molecular orbital reveals that intramolecular charge transfer (ICT) is the key factor for their different opto-electronic properties.
• Naphthalimide‐Based Hydrazone Derivatives: Synthesis, Mechanochromism in the Solid State and Response to Ions in Dilute Solutions
  作者：Shuai Shi、Pei‐Yang Gu、Shiyuan Zhou、Yutao Zhu、Jinghui He、Qingfeng Xu、Jianmei Lu

  DOI：10.1002/cplu.202000764

  日期：2021.1

  mechanochromic luminescence (MCL) are promising for use in the in the fields of sensing and probes. We report the design and synthesis of new naphthalimide‐based hydrazone derivatives, NI‐TPE and NI‐3BA. Both the luminogens are weakly emissive with sΦf=0.3 % and 0.5 % respectively when aggregated in amorphous states as strong π‐π stacking and intermolecular interaction prevent luminescence. On the contrary

  显示出机械致变色发光（MCL）的分子有望用于传感和探针领域。我们报告了基于萘二甲酰亚胺的new衍生物NI‐TPE和NI‐3BA的设计和合成。两个luminogens是弱发射与小号Φ ˚F =分别为0.3％和0.5％无定形状态为强π-π堆积和分子间相互作用聚集时防止发光。相反，在结晶状态下，对两种衍生物的单晶分析表明，非辐射衰变被分子堆积模式和分子间相互作用所减少或抑制。荧光发射强度的增加，以小号Φ ˚F溶剂蒸发后的= 5.5％和6.0％是由于弱的π-π重叠和氢键（NH-⋅⋅⋅O，距离2.99Å），这有利于形成具有松散堆积的分子。同时，两种衍生物在晶格中采用的堆积模式被破坏，从而导致低的固态荧光量子产率和研磨时的红移在23–25 nm之间。所有这些因素导致两个导数显示出异常的“关闭” MCL现象。还证明了在稀溶液中荧光发射，其pH可逆性以及对氟离子和乙酸根离子的选择性响应高达91–93％。