pseudogem-[4-Formyl-13-(4,5-diphenyl-1H-imidazol-2-yl)][2.2]-paracyclophane | 1220516-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: pseudogem-[4-Formyl-13-(4,5-diphenyl-1H-imidazol-2-yl)][2.2]-paracyclophane
• 英文别名: pseudogem-[4-formyl-13-(4,5-diphenyl-1H-imiazol-2-yl)][2.2]paracyclophane；[2.2]paracyclophane-4-(4,5-diphenyl-1H-imidazol-2-yl)-13-carbaldehyde；12-(4,5-diphenyl-1H-imidazol-2-yl)tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene-5-carbaldehyde
• CAS: 1220516-14-2
• 化学式: C₃₂H₂₆N₂O
• 分子量: 454.571
• InChiKey: YFKVEADXQHRNID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pseudogem-[4-Formyl-13-(4,5-diphenyl-1H-imidazol-2-yl)][2.2]-paracyclophane 在 ammonium acetate 、 溶剂黄146 、 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 苯 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Comprehensive Understanding of Structure- Photosensitivity Relationships of Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimers

  摘要：

  The photochromic [2.2]paracyclophane-bridged imidazole dimers show instantaneous coloration upon exposure to UV light and rapid fading in the dark. Experimental details for the enhancement of the photosensitivity and the unique photoisomerization of newly designed [2.2]paracyclophane-bridged imidazole dimers are demonstrated. We explored the structure-property relationships and demonstrated an efficient strategy for designing high-performance fast-photochromic molecules with increased photosensitivity to solar UVA radiation. The [2.2]paracyclophane-bridged imidazole dimer consists of two types of imidazole rings, Im1 and Im2. Im1 is characterized by a 6 pi electron system with an electron-donating characteristic, whereas Im2 is distinguished by a 4 pi electron system with an electron-withdrawing characteristic. The introduction of electron-donating substituents into the phenyl rings attached to the electron-withdrawing Im2 was proved to enhance the photosensitivity with the aid of the intramolecular charge transfer transitions. The unique photoisomerization resulting from the changes in the bonding manner between two imidazole rings was also investigated in detail.

  DOI：

  10.1021/jp201969q
• 作为产物：
  描述：

  4,15-diformyl[2.2]paracyclophane 、 联苯甲酰 在 ammonium acetate 、 溶剂黄146 作用下， 反应 5.0h， 生成 pseudogem-[4-Formyl-13-(4,5-diphenyl-1H-imidazol-2-yl)][2.2]-paracyclophane
  参考文献：
  名称：

  包含咪唑基自由基部分的[2.2]环芳基衍生物的前所未有的自由基反应

  摘要：

  合成了在[2.2]对环环烷（[2.2] PC）部分和咪唑环之间具有C-N键的假单抗-DPIM-DPI [2.2] PC二聚体（3）。这是[2.2] PC衍生物的高度空间受限的1-ene-2,5-环己二烯结构的首次晶体学观察。化合物3表现出光致变色行为，在紫外或可见光照射下，无论在固态还是在室温下，都呈现出从浅黄色到绿色的颜色变化。

  DOI：

  10.1021/ol1017933

文献信息

• Photochromic Properties of [2.2]Paracyclophane-Bridged Imidazole Dimer with Increased Photosensitivity by Introducing Pyrenyl Moiety
  作者：Hiroaki Yamashita、Jiro Abe

  DOI：10.1021/jp204440s

  日期：2011.11.24

  photochromic [2.2]paracyclophane-bridged imidazole dimers show instantaneous coloration upon exposure to UV light and rapid fading in the dark. A new [2.2]paracyclophane-bridged imidazole dimer, pseudogem-PPI-DPI[2.2]PC, with high photosensitivity to UVA radiation was developed. To enhance the photosensitivity, we introduced pyrenyl moieties to the [2.2]paracyclophane-bridged imidazole dimer. The localized

  光致变色[2.2]对环环烷桥连的咪唑二聚体在暴露于紫外线下时会立即显示出颜色，在黑暗中会迅速褪色。一种新的[2.2]对环烷桥联的咪唑二聚体，假宝石开发了对UVA辐射具有高光敏性的-PPI-DPI [2.2] PC。为了增强光敏性，我们将吡啶基部分引入到[2.2]对环环烷桥连的咪唑二聚体中。通过在咪唑环的4位上引入pyr基部分，of基部分的局部π-π*跃迁出现在UVA辐射区域中。π电子系统的扩展也会影响有色物质的吸收光谱。有色物质的宽吸收带覆盖可见光区域的整个范围，并且其吸收率在整个可见光区域大致相等。因此，伪宝石-PPI-DPI [2.2] PC显示出光致变色反应，其在光辐照下呈黑色，并且在室温下遵循单指数动力学具有连续的快速热漂白，时间常数为12 ms。
• Stepwise Two-Photon-Induced Fast Photoswitching via Electron Transfer in Higher Excited States of Photochromic Imidazole Dimer
  作者：Yoichi Kobayashi、Tetsuro Katayama、Takuya Yamane、Kenji Setoura、Syoji Ito、Hiroshi Miyasaka、Jiro Abe

  DOI：10.1021/jacs.6b01470

  日期：2016.5.11

  processes to the photochromic bridged imidazole dimer, whose solution instantly changes color upon UV irradiation and quickly reverts to the initial color thermally at room temperature. We synthesized a zinc tetraphenylporphyrin (ZnTPP)-substituted bridged imidazole dimer, and wide ranges of time-resolved spectroscopic studies revealed that a ZnTPP-linked bridged imidazole dimer shows efficient visible stepwise

  逐步双光子激发引起了很大的兴趣，因为与同时进行的双光子过程相比，它们的功率阈值要低得多，而且一些阶梯式双光子过程可以由弱的非相干激发光源引发。在这里，我们将逐步双光子光学过程应用于光致变色桥连咪唑二聚体，其溶液在紫外线照射下立即改变颜色，并在室温下通过热迅速恢复到初始颜色。我们合成了锌四苯基卟啉 (ZnTPP) 取代的桥连咪唑二聚体，广泛的时间分辨光谱研究表明，ZnTPP 连接的桥连咪唑二聚体在卟啉部分激发时显示出有效的可见逐步双光子诱导的光致变色反应。
• Fast Photochromic Polymers Carrying [2.2]Paracyclophane-Bridged Imidazole Dimer
  作者：Atsushi Kimoto、Atsuhiro Tokita、Takeru Horino、Toyoji Oshima、Jiro Abe

  DOI：10.1021/ma100197z

  日期：2010.4.27

  The synthesis and photochromic behavior of the fast photochromic polymers carrying [2.2]paracyclophane-bridged imidazole dimer are demonstrated. A significant feature of this synthetic strategy is that we can modify the photochromic properties such as coloration/decoloration rate, coloring, and photosensitivity via the stepwise synthetic approach of the imidazole dimer system. Notably, the photochromic behavior of the polymers is not affected by the environment around the photochromes and copolymerization with other monomers in both solution and film, which cannot be realized in any other conventional photochromic systems. The comparable photochromic behavior of the homopolymers and copolymers in solution and film indicates that the photochromic unit is independent from the local environment, which allows effective molecular design of the photochromic monomer unit to accomplish desired photochromic properties of the polymer.
• EP2397468
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL CROSSLINKED HEXAARYL BISIMIDAZOLE COMPOUND AND DERIVATIVE THEREOF, METHOD FOR PRODUCING THE COMPOUND AND PRECURSOR COMPOUND TO BE USED IN THE PRODUCTION METHOD
  申请人：Abe Jiro

  公开号：US20110306743A1

  公开（公告）日：2011-12-15

  Provided is a crosslinked hexaaryl bisimidazole compound which can achieve photochromic characteristics, i.e., visually showing decoloring simultaneously with the stop of light irradiation and enables precise control of color tone, density and so on in coloring. Also provided are a method for producing the aforesaid compound whereby the degrees of freedom in molecular design and synthesis can be increased, and a precursor compound to be used in the production method.