N,N-bis(6'-iodohexyl)-4-aminobenzaldehyde | 766545-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-bis(6'-iodohexyl)-4-aminobenzaldehyde
• 英文别名: 4-[Bis(6-iodohexyl)amino]benzaldehyde
• CAS: 766545-68-0
• 化学式: C₁₉H₂₉I₂NO
• 分子量: 541.254
• InChiKey: LBLJKXLNIGGNNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  536.1±45.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-bis(6'-iodohexyl)-4-aminobenzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 2,6-bis(4-{N,N-bis[6-(4-morpholinyl)hexyl]amino}styryl)naphthalene
  参考文献：
  名称：

  用于生物应用的荧光二苯乙烯基萘衍生物的简便合成†

  摘要：

  合成了一系列新型的2,6-双（4-氨基苯乙烯基）萘基衍生物，并研究了其光谱性质。由于它们的低细胞毒性，合适的光学性质和对生物结构的潜在亲和力，这些衍生物被证明是有前途的染料，可用于基于荧光的生物成像。通过荧光显微术揭示了将测试化合物选择性插入细胞膜中。

  DOI：

  10.1039/c7nj00004a
• 作为产物：
  描述：

  苯胺 在 potassium carbonate 、 sodium iodide 、 三氯氧磷 作用下， 以 丙酮 、 正丁醇 为溶剂， 反应 107.0h， 生成 N,N-bis(6'-iodohexyl)-4-aminobenzaldehyde
  参考文献：
  名称：

  用于生物应用的荧光二苯乙烯基萘衍生物的简便合成†

  摘要：

  合成了一系列新型的2,6-双（4-氨基苯乙烯基）萘基衍生物，并研究了其光谱性质。由于它们的低细胞毒性，合适的光学性质和对生物结构的潜在亲和力，这些衍生物被证明是有前途的染料，可用于基于荧光的生物成像。通过荧光显微术揭示了将测试化合物选择性插入细胞膜中。

  DOI：

  10.1039/c7nj00004a

文献信息

• Solvatochromism of Distyrylbenzene Pairs Bound Together by [2.2]Paracyclophane:  Evidence for a Polarizable “Through-Space” Delocalized State
  作者：Janice W. Hong、Han Young Woo、Bin Liu、Guillermo C. Bazan

  DOI：10.1021/ja044326+

  日期：2005.5.25

  compounds were designed and synthesized to examine how through-space and through-bond electron delocalization respond to solvent effects. The general strategy involves the study of "dimers" of the distyrylbenzene chromophore held in close proximity by the [2.2]paracyclophane core and a systematic dissection of the chromophore into components with through-space and through-bond electronic delocalization. Steady

  设计并合成了一系列化合物，以检查空间和键合电子离域如何响应溶剂效应。一般策略涉及研究由 [2.2] 对环芳核心紧密靠近的二苯乙烯基苯发色团的“二聚体”，以及将发色团系统地分解为具有通过空间和通过键电子离域的组件。一系列溶剂中的稳态和时间分辨荧光光谱显示，当不存在供体取代基时，在极性溶剂中发射状态的发射红移和固有荧光寿命增加。我们提出跨 [2.2] 对环芳烷核心的空间离域在激发态更容易极化，相对于直通键（二苯乙烯基）激发态。当强供体连接到二苯乙烯基苯发色团时，基于二苯乙烯基苯的激发态的电荷转移特性决定了荧光特性。
• Water-soluble distyrylbenzene chromophores for applications in optoelectronic technologies
  申请人：——

  公开号：US20040192968A1

  公开（公告）日：2004-09-30

  Two-photon or multi-photon chromophores having a conjugated pi-electron system with donating groups at each end of the pi-electron system providing charge-transfer properties, and having quaternary amine groups that can enhance the solubility of the chromophore in water. In a particular embodiment, the chromophore is based on a distyrylbenzene core, with donor or acceptor groups attached to the central benzene ring.

  具有共轭π电子系统的双光子或多光子色团，在π电子系统的每个末端具有给电子基团，提供电荷转移特性，并具有可以增强色团在水中溶解度的季铵基团。在特定实施例中，该色团基于二苯乙烯核心，中央苯环上附有供体或受体基团。
• 一种有机-无机杂化量子点及其制备方法与在细胞成像中的应用
  申请人：山东第一医科大学（山东省医学科学院）

  公开号：CN116854725A

  公开（公告）日：2023-10-10

  本发明公开了一种有机‑无机杂化量子点及其制备方法与在细胞成像中的应用，属于量子点细胞成像技术领域。所述有机‑无机杂化量子点的结构式如下：#imgabs0#其中，n＝0、1、2。本发明公开的有机‑无机杂化量子点同样具备传统无机量子的特性：随着纳米粒子尺寸的增大，荧光也逐渐红移；具有较大的斯托克斯位移；荧光量子效率较高(>20％)。通过细胞实验结果表明，本发明的有机‑无机杂化量子点能够有效地被细胞摄取，且变现为极低的细胞毒性以及比传统商业化荧光染料更好的抗光漂白性能。本发明的有机‑无机杂化量子点优异的荧光特性可以很好地对细胞进行荧光标记成像，在生物医学光子学领域具有较好的应用前景。
• Solvent Effects on the Two-Photon Absorption of Distyrylbenzene Chromophores
  作者：Han Young Woo、Bin Liu、Bernhard Kohler、Dmitry Korystov、Alexander Mikhailovsky、Guillermo C. Bazan

  DOI：10.1021/ja052906g

  日期：2005.10.1

  A series of organic- and water-soluble distyrylbenzene-based two-photon absorption (TPA) fluorophores containing dialkylamino donor groups at the termini was designed, synthesized, and characterized. The central core was systematically substituted to modulate intramolecular charge transfer (ICT). These molecules allow an examination of solvent effects on the TPA cross section (delta) and on the TPA action cross section. In toluene, the delta values follow the order of ICT strength. The effect of solvent on delta is nonmonotonic: maximum delta was measured in an intermediate polarity solvent (THF) and was lowest in water. We failed to find a correlation between the observed solvent effect and previous theoretical predictions. Hydrogen bonding to the donor groups and aggregation of the optical units in water, which are not included in calculational analysis, may be responsible for the discrepancies between experimental results and theory.
• Modification of the Optoelectronic Properties of Membranes via Insertion of Amphiphilic Phenylenevinylene Oligoelectrolytes
  作者：Logan E. Garner、Juhyun Park、Scott M. Dyar、Arkadiusz Chworos、James J. Sumner、Guillermo C. Bazan

  DOI：10.1021/ja1016156

  日期：2010.7.28

  We report on the modification of membranes by incorporation of phenylenevinylene oligoelectrolytes with the goal of tailoring their optical and electronic properties and their applications. A water-soluble distyrylstilbene oligoelectrolyte (DSSN+), capped at each end with nitrogen bound, terminally charged pendant groups, was synthesized. The photophysical and solvatochromatic properties of DSSN+ and the shorter distyrylbenzene analogue DSBN+ were probed and found to be useful for characterizing insertion into membranes based on phospholipid vesicle systems. A combination of UV/visible absorbance and photoluminescence spectroscopies, together with confocal microscopy, were employed to confirm membrane incorporation. Examination of the emission intensity profile in stationary multilamellar vesicles obtained with a polarized excitation source provides insight into the orientation of these chromophores within lipid bilayers and indicates that these molecules are highly ordered, such that the hydrophobic electronically delocalized region positions within the inner membrane with the long molecular axis perpendicular to the bilayer plane. Cyclic voltammetry experiments provide evidence that DSSN+ and DSBN+ facilitate transmembrane electron transport across lipid bilayers supported on glassy carbon electrodes. Additionally, the interaction with living microorganisms was probed. Fluorescence imaging indicates that DSSN+ and DSBN+ preferentially accumulate within cell membranes. Furthermore, notable increases in yeast microbial fuel cell performance were observed when employing DSSN+ as the electron transport mediator.