9,9'-(6,6'-diformylbiphenyl-2,2'-diyl)diacridine | 1141733-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9,9'-(6,6'-diformylbiphenyl-2,2'-diyl)diacridine
• 英文别名: 3-Acridin-9-yl-2-(2-acridin-9-yl-6-formylphenyl)benzaldehyde；3-acridin-9-yl-2-(2-acridin-9-yl-6-formylphenyl)benzaldehyde
• CAS: 1141733-51-8
• 化学式: C₄₀H₂₄N₂O₂
• 分子量: 564.643
• InChiKey: XYTUPHSZSORGHF-UHFFFAOYSA-N

物化性质

• 沸点：
  723.9±60.0 °C(predicted)
• 密度：
  1.308±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  44
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9,9'-(6,6'-diformylbiphenyl-2,2'-diyl)diacridine 在 2,6-二叔丁基-4-甲基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成
  参考文献：
  名称：

  Chiral Memory Units Based on Dynamic Redox Systems with a Dibenzoxepinone Skeleton: Drastic Change in Racemization Barrier and Electrochemical Bistability

  摘要：

  The configuration of helical dicationic dyes 2(2+) with a dihydrodibenzoxepinone unit is stable, whereas the corresponding neutral electron donors 1 with a tetrahydrophenanthroxepinone skeleton easily undergo ring-flip. Thanks to their electrochemical bistability, electron exchange between 1 and 2(2+) is prohibited. Thus, the above electrochromic pairs 1/2(2+) can serve as new members of less well-explored redox-based chiral-memory units.

  DOI：

  10.3987/com-13-s(s)93
• 作为产物：
  描述：

  2,2'-(6,6'-dibromobiphenyl-2,2'-diyl)di(1,3-dioxolan) 、 10-(2-甲氧基乙氧基甲基)吖啶-9-酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.0h， 以60%的产率得到9,9'-(6,6'-diformylbiphenyl-2,2'-diyl)diacridine
  参考文献：
  名称：

  分子内Methylacridan-Methylacridinium配合物的菲-4,5-二或相关骨架：几何属性关系的可分离的Ç ？H桥接碳正离子

  摘要：

  桥接间隙：1,6-H-移的快照前体表明较窄Ç  H⋅⋅⋅C +分离（d在ORTEP图）中的标题配合物诱导的更快的退化重排1 +。小于2.7埃的接触距离是必须实现的有机三中心两电子键[C  ħ  C] +，由X射线数据的外推法所指示的。

  DOI：

  10.1002/chem.200801769

文献信息

• Geometrical Remote Steric Effects in 4,5-Disubstituted-9,10-dihydrophenanthrenes: Expansion of Prestrained C⁹–C¹⁰ Bond in Di(spiroacridan) Derivatives
  作者：Kazuhisa Wada、Takashi Takeda、Hidetoshi Kawai、Ryo Katoono、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1246/cl.130502

  日期：2013.10.5

  By attaching bulky substituents at the bay region of di(spiroacridan)-substituted dihydrophenanthrene 1a, the prestrained C9–C10 bond in the dihydrophenanthrene (DHP) skeleton of 1c–1e is expanded from 1.634(2) to 1.649(3)–1.652(6) Å, which demonstrates the bond expansion through remote steric effects. Twisting deformation of the DHP skeleton is the key to transfer the steric bulkiness from the C4/C5 positions to cause the additional strain in the C9–C10 bond.

  通过在二（螺吖啶）取代的二氢菲1a的湾区域附加庞大的取代基，1c-1e的二氢菲（DHP）骨架中的预应变C9-C10键从1.634(2)扩展到1.649(3)-1.652(6) Å，这表明了通过远端立体效应实现的键扩展。DHP骨架的扭曲变形是将C4/C5位置的庞大体积转移到C9-C10键上产生额外应变的关键。
• Halochromic Chiroptical Response of Novel Bis(9-acridinyl)-type Fluorophores with a Helical π Framework
  作者：Tatsuo Nehira、Yasuyo Yoshimoto、Kazuhisa Wada、Hidetoshi Kawai、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1246/cl.2010.165

  日期：2010.3.5

  Acridine-based novel fluorophores 1/2 with a helical dihydrodibenzoxepin/azepine skeleton exhibit halochromic response upon addition of Brønsted acid in CH2Cl2, thus giving UV–vis and fluorescence spectral changes. By using the optically resolved species [(M)-1/2], circular dichroism (CD) and fluorescence detected-CD (FDCD) signals were also changed drastically, thus demonstrating four-way-output response thanks to configurational stability of helicity and efficient exciton coupling.

  基于吖啶的新型荧光团 1/2 具有螺旋二氢二苯并氧杂环庚烷/吖庚因骨架，在 CH2Cl2 中添加布朗斯台德酸后表现出卤色响应，从而产生紫外-可见光和荧光光谱变化。通过使用光学分辨物种[(M)-1/2]，圆二色性（CD）和荧光检测CD（FDCD）信号也发生了巨大变化，从而由于螺旋性和有效的激子耦合。
• Phenanthrene-4,5-diylbis(10-methylacridinium) with a Short C+ - - C+ Contact: Preparation, Molecular Structure, Redox Properties, and Electrochromic Interconversion with Dihydropyrene Derivative
  作者：Takanori Suzuki、Yasuyo Yoshimoto、Kazuhisa Wada、Takashi Takeda、Hidetoshi Kawai、Kenshu Fujiwara

  DOI：10.3987/com-09-s(s)35

  日期：——

  The title dication (1(2+)) was generated by oxidative bond cleavage of a 4,5-dihydoropyrene derivative (2) with two spiro(10-methylacridan) units. Despite the skewed deformation of the arylene spacer, two cationic chromophores in 1(2+) are forced to face in a proximity with a very short interatomic separation of 2.98(1) angstrom between carbenium centers (X-ray), which makes the LUMO level of 1 much lower than that of biphenyl-2,2'-diyl-type dication (3(2+)).
• Intramolecular Methylacridan-Methylacridinium Complexes with a Phenanthrene-4,5-diyl or Related Skeleton: Geometry-Property Relationships in Isolable CH Bridged Carbocations
  作者：Takanori Suzuki、Yasuyo Yoshimoto、Takashi Takeda、Hidetoshi Kawai、Kenshu Fujiwara

  DOI：10.1002/chem.200801769

  日期：2009.2.16

  Bridging the gap: Snapshots of 1,6‐H‐shift precursors indicate that a narrower CH⋅⋅⋅C+ separation (D in the ORTEP diagram) in the title complexes induces faster degenerate rearrangement of 1+. A contact distance of less than 2.7 Å is necessary to realize the organic three‐center two‐electron bond of [CHC]+, as indicated by extrapolation of the X‐ray data.

  桥接间隙：1,6-H-移的快照前体表明较窄Ç  H⋅⋅⋅C +分离（d在ORTEP图）中的标题配合物诱导的更快的退化重排1 +。小于2.7埃的接触距离是必须实现的有机三中心两电子键[C  ħ  C] +，由X射线数据的外推法所指示的。
• Chiral Memory Units Based on Dynamic Redox Systems with a Dibenzoxepinone Skeleton: Drastic Change in Racemization Barrier and Electrochemical Bistability
  作者：Takanori Suzuki、Kazuhisa Wada、Yuna Chiba、Takashi Takeda、Hidetoshi Kawai、Ryo Katoono、Kenshu Fujiwara

  DOI：10.3987/com-13-s(s)93

  日期：——

  The configuration of helical dicationic dyes 2(2+) with a dihydrodibenzoxepinone unit is stable, whereas the corresponding neutral electron donors 1 with a tetrahydrophenanthroxepinone skeleton easily undergo ring-flip. Thanks to their electrochemical bistability, electron exchange between 1 and 2(2+) is prohibited. Thus, the above electrochromic pairs 1/2(2+) can serve as new members of less well-explored redox-based chiral-memory units.