7-(diphenylamino)-9,9-diethylfluorene-2-carbaldehyde | 1092515-58-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-(diphenylamino)-9,9-diethylfluorene-2-carbaldehyde
• 英文别名: 9,9-diethyl-7-(N-phenylanilino)fluorene-2-carbaldehyde
• CAS: 1092515-58-6
• 化学式: C₃₀H₂₇NO
• 分子量: 417.55
• InChiKey: SFPNTNXEOALWAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  7-(diphenylamino)-9,9-diethylfluorene-2-carbaldehyde 在 sodium tetrahydroborate 、 potassium tert-butylate 、 碘 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.25h， 生成 7-[4-(9,9-diphenyl-9H-fluoren-4-yl)styryl]-9,9-diethyl-2-(N,N-diphenylamino)-9H-fluorene
  参考文献：
  名称：

  具有各种芳族封端基团的 2-二苯基氨基芴-7-基苯乙烯衍生物，用于高效蓝光和白色有机发光二极管

  摘要：

  合成并表征了具有 2-二苯基氨基芴-7-基苯乙烯发光单元和各种芳族封端基团的高效蓝色荧光材料。2-甲基-9,10-双（2-萘基）蒽主体掺杂有这些蓝色材料，作为有机发光二极管（OLED）器件发光层中的蓝色掺杂剂。所有器件都表现出高效的蓝色电致发光和高外部量子效率（20 mA cm-2 时为 4.38-6.2 %）。特别是，使用 7-[3,5-bis(naphthalen-1-yl)styryl]-9,9-diethyl-2-N,N-diphenylamino-9H-芴 (1f) 和 7-{ 4-[1'-(2',3',4',5'-四苯基)苯基]苯乙烯基}-9,9-二乙基-2-N,N-二苯基氨基-9H-芴(1g)作为掺杂剂在发光层在 20 mA cm-2 下显示出 4.63 % 和 5.96 % 的高外量子效率，颜色坐标为 (0.148, 0. 134) 和 (0.147, 0.144)，分别。使用

  DOI：

  10.1002/ejoc.201100472
• 作为产物：
  描述：

  2,7-二溴-9,9-二乙基芴 在 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 27.0h， 生成 7-(diphenylamino)-9,9-diethylfluorene-2-carbaldehyde
  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

• 4,5,5-Trimethyl-2,5-dihydrofuran-Based Electron-Withdrawing Groups for NIR-Emitting Push–Pull Dipolar Fluorophores
  作者：Maxime Rémond、Zheng Zheng、Erwann Jeanneau、Chantal Andraud、Yann Bretonnière、Sébastien Redon

  DOI：10.1021/acs.joc.9b01120

  日期：2019.8.16

  (benzo[d]thiazol-2-yl) moiety failed, and unexpected structures were obtained. On the other hand, phenylthio and phenylsulfonyl entities were successfully introduced at position 3 of the 2-(dicyanomethylidene)-2,5-dihydrofuran ring, giving access to new electron-acceptor groups and dipolar fluorophores displaying near-infrared emission in solution or in the solid state, brighter than their TCF analogues.

  在推挽偶极染料的分子工程学背景下，我们介绍了著名的电子接受基团2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran（TCF）。（苯并[ d ]噻唑-2-基）部分的引入失败，并且获得了意外的结构。另一方面，苯硫基和苯磺酰基实体已成功地引入到2-（二氰基亚甲基）-2,5-二氢呋喃环的3位，从而可以接触到新的电子受体基团和在溶液或溶液中显示近红外发射的偶极荧光团。固态，比其TCF类似物亮。
• [EN] NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS ÉLECTROLUMINESCENTS ORGANIQUES, ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE UTILISANT CES COMPOSÉS
  申请人：DOW ADVANCED DISPLAY MAT LTD

  公开号：WO2010140801A1

  公开（公告）日：2010-12-09

  Provided are novel organic electroluminescent compounds and an organic electroluminescent device including the same. The disclosed organic electroluminescent compounds exhibit high luminescence efficiency in blue color and excellent life property. Thus, they may be used to manufacture OLEDs having very good operation life.

  提供了新型有机电致发光化合物以及包括这些化合物的有机电致发光装置。公开的有机电致发光化合物在蓝色方面表现出高发光效率和优秀的寿命特性。因此，它们可以用于制造具有非常良好使用寿命的OLED。
• Photostable far-red emitting pluronic silicate nanoparticles: perfect blood pool fluorophores for biphotonic in vivo imaging of the leaky tumour vasculature
  作者：Zheng Zheng、Flavien Caraguel、Yuan-Yuan Liao、Chantal Andraud、Boudewijn van der Sanden、Yann Bretonnière

  DOI：10.1039/c6ra17438h

  日期：——

  A new non-diffusible fluorescent probe for two photon microscopy, comprising a hydrophobic push-pull dye in the apolar core of Pluronic F127–silica nanoparticles, shows intense red emission (Φ_f 39% at 650 nm) and two-photon absorption properties in the NIR.

  一种新的不可扩散荧光探针用于双光子显微镜，包括一个疏水推-拉染料在Pluronic F127-二氧化硅纳米粒子的无极性核心中，显示出强烈的红色发射（在650纳米处的Φf 39%）和近红外区域的双光子吸收特性。
• The synthesis and spectral characterization of red dyes containing biphenyl or fluorene conjugation and dicyanovinyl acceptors
  作者：Abhishek Baheti、Prachi Singh、K.R. Justin Thomas

  DOI：10.1016/j.dyepig.2010.06.008

  日期：2011.2

  acceptors and either a fluorene or biphenyl linker were prepared in an attempt to unravel the similarities and differences between the biphenyl and fluorene segments in donor–acceptor architectures. The linker segments significantly modify λmax and the redox potential of the dyes is influenced by the nature of both the amine and linker. Density functional theory calculations performed at the 6-31G(d

  制备了含有二芳基胺供体，双氰基乙烯基受体以及芴或联苯连接基的新型偶极化合物，试图揭示供体-受体结构中联苯和芴链段之间的相似性和差异。该连接段显著修改λ最大染料的氧化还原电势受胺和接头性质的影响。在6-31G（d，p）水平执行的密度泛函理论计算表明，较高的波长吸收包含胺供体与双氰基乙烯基受体之间的电荷转移跃迁，这是主要的贡献。HOMO主要位于三芳基胺链段上，而LUMO则分布在二氰基乙烯基上。芴基染料显示出比联苯类似物低的热稳定性。
• Blue emitting materials based on diphenylamine-substituted diphenylvinylarenes for OLEDs
  作者：Changmin Kim、Sujin Jeong、Ho Won Lee、Young Kwan Kim、Seung Soo Yoon

  DOI：10.1080/15421406.2017.1338486

  日期：2017.7.3

  To develop the efficient blue emitters for Organic light-emitting diodes (OLEDs), this paper reports the synthesis and electroluminescent properties of diphenylvinylarenes end-capped with diphenylamine groups. Two OLEDs were fabricated in the following sequence: indium-tin-oxide (ITO) / N,N-di(1-naphthyl)-N,N-diphenyl-(1,1-biphenyl)-4,4-diam-ine (NPB) (50nm) / Blue emitters (30nm) / bathophenanthroline (Bphen) (30nm) / lithium quinolate (Liq) (2nm) /Al (100nm). Two devices exhi-bited blue electroluminescence. In particular, a device using 9,9-diethyl-N,N-diphenyl-7-(2,2-diphenylvinyl)-9H-fluoren-2-amine exhibited blue emission with a luminance efficiency, a power efficiency, an external quantum efficiency and Commission Internationale d'Enclairage (CIE) coordinates of 5.48 cd/A, 2.45lm/W, 2.85% at 20mA/cm(2) and (x = 0.17, y = 0.25) at 8.0V, respectively.