9,9-二己基-9H-芴-2,7-二甲醛 | 295796-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 9,9-二己基-9H-芴-2,7-二甲醛
• 英文名称: 9,9-dihexyl-9H-fluorene-2,7-dicarbaldehyde
• 英文别名: 9,9-dihexyl-fluorene-2,7-dicarbaldehyde；9,9-dihexylfluorene-2,7-dicarbaldehyde
• CAS: 295796-57-5
• 化学式: C₂₇H₃₄O₂
• 分子量: 390.566
• InChiKey: MUCZWOKWOVOMCK-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  539.5±43.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9-二己基-9H-芴-2,7-二甲醛 在 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 33.0h， 生成 2,7-diethenyl-9,9-di-n-hexylfluorene
  参考文献：
  名称：

  Alternating Aromatic and Transannular Chromophores with and without Linker:  Effect of Transannular π−π Interaction on the Optical Property of Dithiaparacyclophane-based Copolymers

  摘要：

  A series of bithiophene-cyclophane (PPP-type), acetylene-fluorene-acetylene-cyclophane (PPE-type), and ethylene-fluorene-ethylene-cyclophane (PPV-type) copolymers, namely, 4-6, was synthesized via a nickel-catalyzed reaction, a palladium-catalyzed Sonagashira reaction, and a Heck coupling, respectively. Unlike in the fluorene-cyclophane copolymer 3, the transannular pi-pi interaction of the cylophane unit in copolymer 4 resulted in a significant blue shift in its emission spectrum compared to a reference polymer, giving it an essentially blue emitting light. By introducing an acetylene or ethylene linker in going from 3 to 5 or 6, the effective conjugation in the polymer backbone due to higher rigidity in coplanarity decreased the effect of the transannular pi-pi interaction. While the PPV-type copolymer 6 still exhibited an appreciable red shift in both absorption and emission with respect to a reference polymer, negligible shifts were observed for copolymer 5.

  DOI：

  10.1021/ma035902+
• 作为产物：
  描述：

  9,9-二己基-2,7-二溴代芴 在 重铬酸吡啶 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 9,9-二己基-9H-芴-2,7-二甲醛
  参考文献：
  名称：

  Design, Synthesis, and Electroluminescent Property of CN−Poly(dihexylfluorenevinylene) for LEDs

  摘要：

  A new green electrolumineseence polymer, CN-poly(dihexylfluorenevinylene) (CN-PDHFV), which denotes poly [(9,9-dihexyl-9H-fluorene-2,7-diyl)(1-cyanoethene-1,2-diyl)(9,9-dihexyl-9H-fluorene-2,7-diyl)(2-cyaoethene-1,2-diyl)], was synthesized by condensation polymerization utilizing the Knoevenagel reaction. The resulting polymer exhibits good solubility in common organic solvents such as chloroform, THF, and ODCB. The polymer is also easily cast on a glass plate to green film. The UV-vis spectrum of the polymer exhibits characteristically a broad absorption band at 440 nm. This polymer shows photoluminescence around lambda(max) = 535 nm (exciting wavelength 410 nm) and green electroluminescence around.. = 530 nm. The current-voltage-luminance (I-V-L) characteristics of the polymer show a turn-on voltage of 4.8 V and a brightness of 600 cd/m(2) at 5.8 V in the Al/polymer/PEDOT/ITO device. The highest efficiency was observed to be 0.85 1m/W at 5.6 V.

  DOI：

  10.1021/ma025862u

文献信息

• Tunable Fluorene-Based Dynamers through Constitutional Dynamic Chemistry
  作者：Nicolas Giuseppone、Gad Fuks、Jean-Marie Lehn

  DOI：10.1002/chem.200501037

  日期：2006.2.8

  Dynamic covalent iminofluorene-based oligomers and polymers have been generated. They undergo constitutional recomposition under the effect of two parameters, acidity and ZnII metal ions. As a result, marked changes in physical properties take place. The results illustrate the response of such a dynamic system to chemical effectors (H+ nd ZnII), thus demonstrating the adaptive behavior of the system

  已经产生了动态的基于共价亚氨基芴的低聚物和聚合物。它们在酸度和ZnII金属离子两个参数的作用下进行结构重组。结果，物理性能发生了明显的变化。结果说明了这种动态系统对化学效应物（H + nd ZnII）的响应，从而证明了系统在外部因素压力下的自适应行为。他们还指出了通过响应特定触发而进行结构重组来调节光学特性（紫外线可见吸收和荧光）的可能性。这些特征允许开发动态材料，其功能特性可以响应外部刺激。
• Turning-on the Quenched Fluorescence of Azomethines through Structural Modifications
  作者：Satyananda Barik、William G. Skene

  DOI：10.1002/ejoc.201201502

  日期：2013.5

  fluorene azomethines were prepared to examine the effect of structural modification on the absolute fluorescence quantum yields (Φfl). The change in fluorescence occurring upon reversing the orientation of the azomethine bond, the number of fluorene units, and alkylation at the 9,9′-positions of fluorene was examined. It was found that Φfl could be tailored with these structural modifications with 0

  制备了一系列芴偶氮甲碱以检查结构修饰对绝对荧光量子产率 (Φfl) 的影响。检查了在反转偶氮甲碱键的方向、芴单元的数量和芴的 9,9'-位置的烷基化时发生的荧光变化。发现 Φfl 可以通过这些结构修改进行调整，0.05 ≤ Φfl ≤ 0.45。对于衍生自 2,7-二氨基芴的三聚体测量最高 Φfl，每个芴在 9,9'-位被烷基化。荧光量子产率在 77 K 时没有增加，这意味着不存在涉及内部转换的荧光猝灭模式。在用三氟乙酸质子化亚胺时也没有观察到荧光增强。这证实 Waldon 反转和异构化不是荧光失活模式。此外，当芴衍生物在 354 nm 下照射时，在室温或 77 K 下均未观察到光异构化。相比之下，N-亚苄基苯胺类似物的 Z 光异构体通过吸光度和 1 H NMR 光谱进行光谱检测。
• Towards multichromatic electrochromes from ambipolar conjugated azomethines
  作者：Michael E. Mulholland、Daminda Navarathne、Samim Khedri、W. G. Skene

  DOI：10.1039/c4nj00027g

  日期：——

  A series of conjugated azomethines end-capped with phenylamides and consisting of different aromatic cores of varying π-donor strength were prepared. Their optical and electrochemical properties were investigated to assess the suitability of the azomethines as electrochromic materials. The azomethines were found to undergo both electrochemical oxidation and reduction in the window of −1.60 and +1.35 V vs. Ag/Ag+. The color of the ambipolar compounds could be dramatically changed when switched between their reduced, neutral, and oxidized states. The color of the different states was contingent on the π-donor strength of the central aromatic unit. The largest spectral difference of 350 nm between the reduced and oxidized states was observed when the central aromatic group was 3,4-ethylenedioxythiophene (EDOT). The colors detectable by the eye for this EDOT derivative were blue, red, and bleached for the reduced, neutral, and oxidized states, respectively. The multichromatic azomethine was used as an electrochromic layer in a functioning device. The proof-of-concept ambipolar electrochromic device could be repeatedly switched between its orange (neutral) and purple (reduced) states. The device could also be switched to its oxidized (bleached) state.

  制备了一系列以苯基酰胺封端的共轭偶氮甲烷，它们由具有不同π-供体强度的不同芳香族核组成。研究人员对其光学和电化学性质进行了研究，以评估偶氮甲烷作为电致变色材料的适用性。研究发现，偶氮甲烷在-1.60和+1.35 V vs. Ag/Ag+的范围内会发生电化学氧化和还原。当在还原、中和氧化状态之间切换时，双极化化合物的颜色会发生显著变化。不同状态的颜色取决于中心芳香基团的π-供体强度。当中心芳香基团为3,4-乙撑二氧噻吩（EDOT）时，还原和氧化状态之间的最大光谱差异为350 nm。对于这种EDOT衍生物，还原、中和氧化状态的颜色分别为蓝色、红色和漂白色，肉眼可识别。多色偶氮甲烷被用作功能性器件中的电致变色层。这种双极电致变色器件的概念验证可以在橙色（中性）和紫色（还原）状态之间反复切换。该器件还可以切换到氧化（漂白）状态。
• [EN] TRIPLET QUENCHER<br/>[FR] EXTINCTEUR DE TRIPLET
  申请人：UNIV QUEENSLAND

  公开号：WO2022073065A1

  公开（公告）日：2022-04-14

  The disclosure relates to a substituted cyclooctatetraene triplet excited-state quencher compound of Formula (I): wherein: Z is a wide band gap moiety; L is a non-conjugating linker group; each R, which may be the same or different, is a non- conjugating substituent; n is an integer from 0 to 7; and m is an integer from 1 to 6. The disclosure further relates to use of such compounds as triplet quenchers, compositions comprising such compounds, films or coatings comprising said compounds or compositions, and use of said compositions or films or coatings as active gain media for light amplification.

  本发明涉及一种式为(I)的取代环辛四烯三重激发态猝灭剂化合物，其中：Z是宽带隙基团；L是非共轭连接基团；每个R，可以相同也可以不同，是非共轭取代基；n是0到7的整数；m是1到6的整数。本发明还涉及将这种化合物用作三重态猝灭剂、包含这种化合物的组合物、包含所述化合物或组合物的薄膜或涂层，以及将所述组合物或薄膜或涂层用作光放大的有源增益介质的使用。
• Poly(arylene vinylene) Synthesis via a Precursor Step-Growth Polymerization Route Involving the Ramberg–Bäcklund Reaction as a Key Post-Chemical Modification Step
  作者：Kunche Aravindu、Eric Cloutet、Cyril Brochon、Georges Hadziioannou、Joan Vignolle、Frédéric Robert、Daniel Taton、Yannick Landais

  DOI：10.1021/acs.macromol.8b00676

  日期：2018.8.14

  copolymers based on poly(fluorene vinylene) [PFV] and poly(fluorene vinylene-co-carbazole vinylene) [PFVCV] was achieved via a previously unexplored precursor three-step synthetic route involving the Ramberg–Bäcklund reaction. The resulting π-conjugated (co)polymers proved highly soluble in common organic solvents, such as DCM, THF, or CHCl3. The solution step-growth polymerization between 2,7-bis(bromomethyl)-9

  基于聚（芴亚乙烯基）[共轭共聚物的合成PFV ]和聚（芴vinylene-共-咔唑亚乙烯基）[ PFVCV ]经由涉及兰堡-巴克伦反应以前未开发的前体的三步合成路线来实现。事实证明，所得的π-共轭（共）聚合物可高度溶于常见的有机溶剂，例如DCM，THF或CHCl 3。2,7-双（溴甲基）-9,9'-二己基-9 H-芴[ F-Br ]和2,7-双（巯基甲基）-9,9'-二己基-9之间的溶液逐步增长聚合H-芴[ F-SH在碱性条件下于100℃在MeOH和THF的混合物中进行]。然后，使用m- CPBA对所得的多硫化物进行氧化反应，然后在CF 2 Br 2 / Al 2 O 3 -KOH存在下进行Ramberg-Bäcklund反应，从而获得所需的PFV。类似地，PFVCV可以通过相同的三个步骤的序列用人来合成，在此情况下，2,7-双（巯基甲基）-9-（十三烷-7-基）-9 ħ -咔唑（C-SH）和F-