N,N-bis[4'-(6''-chlorohexyl)phenyl]-4-aminobenzaldehyde | 845640-44-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis[4'-(6''-chlorohexyl)phenyl]-4-aminobenzaldehyde
• 英文别名: N,N-bis[4'-(6-chlorohexyl)phenyl]-4-amino-benzaldhyde；4-[4-(6-chlorohexyl)-N-[4-(6-chlorohexyl)phenyl]anilino]benzaldehyde
• CAS: 845640-44-0
• 化学式: C₃₁H₃₇Cl₂NO
• 分子量: 510.547
• InChiKey: MPCXZNVZWDZTPY-UHFFFAOYSA-N

物化性质

• 沸点：
  642.7±55.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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[4'-(6''-chlorohexyl)phenyl]-4-aminobenzaldehyde 、 (4,7,12,15)-tetra(diethylphosphonatemethyl)[2.2]paracyclophane 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以61%的产率得到4,7,12,15-tetra-[N,N-bis(4''-(6'''-chlorohexyl)phenyl)4'-aminostyryl]-[2.2]paracyclophane
  参考文献：
  名称：

  Water-Soluble [2.2]Paracyclophane Chromophores with Large Two-Photon Action Cross Sections

  摘要：

  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.

  DOI：

  10.1021/ja0440811
• 作为产物：
  描述：

  二溴三苯胺 在 叔丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 4.5h， 生成 N,N-bis[4'-(6''-chlorohexyl)phenyl]-4-aminobenzaldehyde
  参考文献：
  名称：

  Water-Soluble [2.2]Paracyclophane Chromophores with Large Two-Photon Action Cross Sections

  摘要：

  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.

  DOI：

  10.1021/ja0440811

文献信息

• 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 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.
• US7232913B2
  申请人：——

  公开号：US7232913B2

  公开（公告）日：2007-06-19
• 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.