2-((2-(di-p-tolylamino)-9,9-diethylfluoren-7-yl)methylene)malononitrile | 1416700-62-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-((2-(di-p-tolylamino)-9,9-diethylfluoren-7-yl)methylene)malononitrile
• 英文别名: 2-[[9,9-diethyl-7-(4-methyl-N-(4-methylphenyl)anilino)fluoren-2-yl]methylidene]propanedinitrile
• CAS: 1416700-62-3
• 化学式: C₃₅H₃₁N₃
• 分子量: 493.651
• InChiKey: ZXIAZXBILZBRKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,7-二溴-9,9-二乙基芴 在 aluminum (III) chloride 、 正丁基锂 、 三叔丁基膦 、 palladium diacetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 55.0h， 生成 2-((2-(di-p-tolylamino)-9,9-diethylfluoren-7-yl)methylene)malononitrile
  参考文献：
  名称：

  Design, Synthesis, and Structural and Spectroscopic Studies of Push–Pull Two-Photon Absorbing Chromophores with Acceptor Groups of Varying Strength

  摘要：

  A new series of unsymmetrical diphenylaminofluorene-based chromophores with various strong g-electron acceptors were synthesized and fully characterized. The systematic alteration of the structural design facilitated the investigation of effects such as molecular symmetry and strength of electron-donating and/or -withdrawing termini have on optical nonlinearity. In order to determine the electronic and geometrical properties of the novel compounds, a thorough investigation was carried out by a combination of linear and nonlinear spectroscopic techniques, single-crystal X-ray diffraction, and quantum chemical calculations. Finally, on the basis of two-photon absorption (2PA) cross sections, the general trend for pi-electron accepting ability, i.e., ability to accept charge transfer from diphenylamine was: 2-pyran-4-ylidene malononitrile (pyranone) > dicyanovinyl > bis(dicyanomethylidene)indane >1-(thiophen-2-yl)propenone > dicyanoethylenyl >3-(thiophen-2-yl)propenone. An analogue with the 2-pyran-4-ylidene malononitrile acceptor group exhibited a nearly 3-fold enhancement of the 2PA cross section (1650 GM at 840 nm), relative to other members of the series.

  DOI：

  10.1021/jo302423p

文献信息

• Design, Synthesis, and Structural and Spectroscopic Studies of Push–Pull Two-Photon Absorbing Chromophores with Acceptor Groups of Varying Strength
  作者：Alma R. Morales、Andrew Frazer、Adam W. Woodward、Hyo-Yang Ahn-White、Alexandr Fonari、Paul Tongwa、Tatiana Timofeeva、Kevin D. Belfield

  DOI：10.1021/jo302423p

  日期：2013.2.1

  A new series of unsymmetrical diphenylaminofluorene-based chromophores with various strong g-electron acceptors were synthesized and fully characterized. The systematic alteration of the structural design facilitated the investigation of effects such as molecular symmetry and strength of electron-donating and/or -withdrawing termini have on optical nonlinearity. In order to determine the electronic and geometrical properties of the novel compounds, a thorough investigation was carried out by a combination of linear and nonlinear spectroscopic techniques, single-crystal X-ray diffraction, and quantum chemical calculations. Finally, on the basis of two-photon absorption (2PA) cross sections, the general trend for pi-electron accepting ability, i.e., ability to accept charge transfer from diphenylamine was: 2-pyran-4-ylidene malononitrile (pyranone) > dicyanovinyl > bis(dicyanomethylidene)indane >1-(thiophen-2-yl)propenone > dicyanoethylenyl >3-(thiophen-2-yl)propenone. An analogue with the 2-pyran-4-ylidene malononitrile acceptor group exhibited a nearly 3-fold enhancement of the 2PA cross section (1650 GM at 840 nm), relative to other members of the series.