4-[双(6-氯己基)氨基]苯甲醛 | 766545-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[双(6-氯己基)氨基]苯甲醛
• 英文名称: N,N-bis(6'-chlorohexyl)-4-aminobenzaldehyde
• 英文别名: 4-[Bis(6-chlorohexyl)amino]benzaldehyde
• CAS: 766545-67-9
• 化学式: C₁₉H₂₉Cl₂NO
• 分子量: 358.351
• InChiKey: ATIXVRZJJVEIHX-UHFFFAOYSA-N

物化性质

• 沸点：
  497.3±40.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 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：

  4-[双(6-氯己基)氨基]苯甲醛 在 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 48.0h， 生成 1,4-bis(4'-(N,N-bis(6''-iodohexyl)amino)styryl)-2,5-dimethoxybenzene
  参考文献：
  名称：

  Solvent Effects on the Two-Photon Absorption of Distyrylbenzene Chromophores

  摘要：

  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.

  DOI：

  10.1021/ja052906g
• 作为产物：
  描述：

  6-氯-1-己醇 在 potassium carbonate 、 三氯氧磷 作用下， 以 正丁醇 为溶剂， 反应 98.0h， 生成 4-[双(6-氯己基)氨基]苯甲醛
  参考文献：
  名称：

  由 [2.2] 对环烷结合在一起的二苯乙烯基苯对的溶剂致变色：可极化“穿越空间”离域状态的证据

  摘要：

  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。

  DOI：

  10.1021/ja044326+

文献信息

• Facile synthesis of fluorescent distyrylnaphthalene derivatives for bioapplications
  作者：Beata Łukasik、Justyna Milczarek、Roza Pawlowska、Remigiusz Żurawiński、Arkadiusz Chworos

  DOI：10.1039/c7nj00004a

  日期：——

  A series of novel 2,6-bis(4-aminostyryl)naphthalene based derivatives were synthesized and their spectroscopic properties investigated. Due to their low cytotoxicity, suitable optical properties and potential affinity towards biological structures these derivatives were proved to be promising dyes for application in fluorescence-based bioimaging. Selective intercalation of the tested compounds into

  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。
• Paracyclophane molecules for two-photon absorption applications
  申请人：Bazan C. Guillermo

  公开号：US20060208235A1

  公开（公告）日：2006-09-21

  Chromophores having two-photon or other multi-photon absorptivity. The chromophores are based on a structure of four stilbenoid groups attached to a paracyclophane core, where each stilbenoid group comprises a nitrogen-containing organic group attached by its nitrogen atom to a stilbenoid arm. In particular embodiments, at least one of the stilbenoid groups includes a sulfonium, ammonium, selenium, iodonium or phosphonium moiety. The chromophores have utility as photo-polymerization initiators and two-photon fluorophores for biological imaging.

  具有双光子或其他多光子吸收性的色素团。这些色素团基于连接到对环芳烃核心的四个苯乙烯基团的结构，其中每个苯乙烯基团包括一个含氮有机基团，通过其氮原子连接到苯乙烯基团。在特定实施例中，至少一个苯乙烯基团包括硫鎓、铵鎓、硒鎓、碘鎓或磷鎓基团。这些色素团可用作光聚合引发剂和生物成像的双光子荧光团。
• 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。
• Water-Soluble [2.2]Paracyclophane Chromophores with Large Two-Photon Action Cross Sections
  作者：Han Young Woo、Janice W. Hong、Bin Liu、Alexander Mikhailovsky、Dmitry Korystov、Guillermo C. Bazan

  DOI：10.1021/ja0440811

  日期：2005.1.1

  A series of alpha,omega-donor-substituted distyrylbenzene dimers held together by the [2.2]paracyclophane core were designed, synthesized, and characterized. Different substituents were chosen to modulate the strength of the donor nitrogen groups and to allow the molecules to be either neutral and soluble in nonpolar organic solvents or charged and water-soluble. The specific neutral structures are (in order of decreasing donor strength) 4,7,12,15-tetra[N,N-bis(6' '-chlorohexyl)-4'-aminostyryl]-[2.2]paracyclophane (1N), 4,7,12,15-tetra[(N-(6' '-chlorohexyl)carbazol-3'-yl)vinyl]-[2.2]paracyclophane (2N), and 4,7,12,15-tetra[N,N-bis(4' '-(6' ''-chlorohexyl)phenyl)-4'-aminostyryl]-[2.2]paracyclophane (3N). The charged species are 4,7,12,15-tetra[N,N-bis(6' '-(N,N,N-trimethylammonium)hexyl)-4'-aminostyryl]-[2.2]paracyclophane octaiodide (1C), 4,7,12,15-tetra[(N-(6' '-(N,N,N-trimethylammonium)hexyl)carbazol-3'-yl)vinyl]-[2.2]paracyclophane octaiodide (2C), and 4,7,12,15-tetra[N,N-bis(4' '-(6' ''-(N,N,N-trimethylammonium)hexyl)phenyl)-4'-aminostyryl]-[2.2]paracyclophane octaiodide (3C). Two-photon excitation spectra, measured using the two-photon induced fluorescence technique, show in toluene the following trend for the two-photon cross sections (delta): 3N > 2N > 1N. In water the delta values follow the same order, 3C approximately 2C > 1C, but are smaller (approximately one-third). Significantly, the fluorescence quantum yield (eta) in water decreases much more for 1, relative to 2 and 3. The two-photon action cross sections (deltaeta) of 2C and 3C are 294 GM and 359 GM, respectively. These values are among the highest reported thus far. These results show that, to maximize the deltaeta in this class of chromophores, one needs to fine-tune the magnitude of the charge transfer character of the excited state, to minimize fluorescence quenching in polar media.
• Water-Soluble Two-Photon Fluorophores Based on Paracyclophane
  作者：Han Young Woo、Guillermo C. Bazan

  DOI：10.1080/15421400801925075

  日期：2008.4.17

  We report the synthesis, linear and nonlinear spectroscopy of the paracyclophane-based two-photon absorption (TPA) fluorophores. Two-photon induced fluorescence (TPIF) measurements in water show a substantial decrease in TPA cross section (delta) and fluorescence quantum yield (eta), relative to toluene. We note that to obtain optimum two-photon action cross sections (eta delta) in water, one needs to fine tune the intramolecular charge transfer (ICT). Microenvironment modulation using the micellar structure in water increases eta delta values similar to those obtained in toluene. The measured eta delta values in water are the highest among reported so far, suggesting important guidelines for designing of optimized TPIF molecular-labels.