7-溴-9,9-二辛基芴-2-甲醛 | 534600-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 7-溴-9,9-二辛基芴-2-甲醛
• 英文名称: 7-bromo-9,9-dioctylfluorene-2-carbaldehyde
• 英文别名: 7-bromo-9,9-dioctyl-9H-fluorene-2-carbaldehyde
• CAS: 534600-14-1
• 化学式: C₃₀H₄₁BrO
• 分子量: 497.559
• InChiKey: KOXQYJOFXQCICJ-UHFFFAOYSA-N

物化性质

• 沸点：
  574.8±43.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-溴-9,9-二辛基芴-2-甲醛 在 potassium tert-butylate 、 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 (E)-4-(2-(9,9-dioctyl-7-vinyl-9H-fluoren-2-yl)vinyl)-N,N-diphenylaniline
  参考文献：
  名称：

  Fluorenylvinylenes bridged triphenylamine-based dyes with enhanced performance in dye-sensitized solar cells

  摘要：

  We have synthesized a series of new dipolar organic dyes Bn (n=0, 1, 2) employing triarylamine as the electron-donor, 2-cyanoacrylic acid as the electron-acceptor, and fluorenevinylene as the conjugated bridge, which were used as sensitizers in dye-sensitized solar cells. It is found that the solar-energy-to-electricity conversion efficiencies of the prepared DSSCs are in the range of 2.79-5.56%, which reach 35-70% of a standard device based on N719 fabricated and measured under the same conditions. The DSSC sensitized with B1 with balanced length of conjugated bridge shows the highest photo-to-electrical energy conversion efficiency and the open-circuit photovoltage (V-oc) of 0.86 V. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.008
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 9,9-二辛基-2,7-二溴代芴 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 1.0h， 以61%的产率得到7-溴-9,9-二辛基芴-2-甲醛
  参考文献：
  名称：

  具有四个单分散低聚芴臂的卟啉作为高效的红光发光材料

  摘要：

  通过使用两个关键反应：Lindsey 缩合和 Suzuki-Miyaura 交叉偶联反应，制备了一系列具有四个单分散共轭低聚芴臂的红色发光星形卟啉。所有卟啉都表现出高量子产率（约0.22）和在常见有机溶剂中的良好溶解性，并形成高质量的固体薄膜。光学研究表明，星形低聚物可以通过从芴链段到卟啉核的有效能量转移来吸收蓝光并发出饱和红光。

  DOI：

  10.1021/ja039832y

文献信息

• Harnessing “Click”-Type Chemistry for the Preparation of Novel Electronic Materials
  作者：Michal Firstenberg、Kammasandra Nanjunda Shivananda、Irit Cohen、Olga Solomeshch、Vladislav Medvedev、Nir Tessler、Yoav Eichen

  DOI：10.1002/adfm.201001893

  日期：2011.2.22

  Sequence‐independent or “click”‐type chemistry is applied for the preparation of novel π‐conjugated oligomers. A variety of bi‐functional monomers for Wittig–Horner olefination are developed and applied in a sequential protection–deprotection process for the preparation of structurally similar π‐conjugated oligomers. Selected oligomers are incorporated as the organic semiconductors in light‐emitting

  不依赖序列或“点击”型化学方法可用于制备新型π共轭低聚物。开发了多种用于Wittig-Horner烯烃化的双功能单体，并将其应用于顺序保护-脱保护过程中，以制备结构相似的π共轭低聚物。选定的低聚物被用作发光二极管和场效应晶体管中的有机半导体，证明了这种方法的潜力。
• Synthesis of star-shaped monodisperse oligo(9,9-di-n-octylfluorene-2,7-vinylene)s functionalized truxenes with two-photon absorption properties
  作者：Huipeng Zhou、Xin Zhao、Tianhao Huang、Ran Lu、Hanzhuang Zhang、Xiaohui Qi、Pengchong Xue、Xingliang Liu、Xiaofei Zhang

  DOI：10.1039/c0ob00803f

  日期：——

  of new star-shaped monodisperse conjugated truxene derivatives bearing oligo(fluorene-vinylene) arms (Tr-OFVn, n = 1, 2, 3, 4) have been synthesized. It is found that the conjugation of the oligomers can be extended with prolonging the arms. Notably, the branched oligomers Tr-OFVn without strong donor and acceptor units exhibit two-photon absorption properties, and the two-photon absorption cross sections

  合成了一系列带有低聚（芴-亚乙烯基）臂（Tr-OFV n，n = 1、2、3、4）的新型星形单分散共轭富勒烯衍生物。发现可以通过延长臂来延长低聚物的缀合。值得注意的是，支链低聚物TR-OFV Ñ没有强大的供体和受体单元表现出双光子吸收属性，和双光子吸收截面（δ最大值随在所述臂的芴-亚乙烯基单元的数目）的增加。的最大值δ最大值达到8073 GM化合物TR-OFV4，这使其成为具有增强的TPA横截面的最具竞争力的化合物之一。它为开发强TPA化合物提供了一个新平台，其中扩展的π共轭体系不存在强供体和受体单元。
• Synthesis and photophysical properties of monodisperse oligo(9,9-di-n-octylfluorene-2,7-vinylene)s functionalized anthracenes
  作者：Huipeng Zhou、Ran Lu、Xin Zhao、Xianping Qiu、Pengchong Xue、Xingliang Liu、Xiaofei Zhang

  DOI：10.1016/j.tetlet.2010.07.155

  日期：2010.10

  Four new well-defined monodisperse linear oligofluorenes with anthracene core An-OFVn (n = 1–4) have been synthesized through Heck and Wittig reaction. These conjugated oligomers exhibit good solubility in common organic solvents. It is found that the conjugation length of the oligomers can be extended and the formation of excimers can be suppressed with increasing the number of fluorene–vinylene units

   通过Heck和Wittig反应合成了四种新的定义明确的具有蒽核心An-OFVn（n = 1-4）的单分散线性低聚芴。这些共轭低聚物在普通有机溶剂中显示出良好的溶解性。研究发现，通过增加在蒽的9,10位连接的芴-亚乙烯基单元的数量，可以延长低聚物的共轭长度，并抑制准分子的形成。
• Understanding the reversible anodic behaviour and fluorescence properties of fluorenylazomethines — A structure–property study
  作者：Satyananda Barik、Sayuri Friedland、W. G. Skene

  DOI：10.1139/v10-080

  日期：2010.9

  A series of fluorenylazomethine dyads and triads were prepared by simple condensation between the corresponding amine and aldehyde fluorene derivatives. These compounds were prepared as model compounds for investigating the effects of substitution and electronic groups on both the electrochemical properties and fluorescence quantum yields. It was found that the oxidation potential could be decreased by both incorporating electron donating groups and increasing the degree of conjugation. It was further found that alkylation in the fluorene’s 9-position increased the azomethine degree of conjugation by forcing all the fluorene moieties to be coplanar with the azomethine bonds to which they are attached. Meanwhile, reversible radical cation behaviour was possible by substituting the terminal 2,2′-positions with atoms other than hydrogen. The radical cation was theoretically found to be distributed evenly across the fluorene, corroborating the reversible anodic behaviour with 2,2′-substitution. The fluorescence quantum yields of the azomethines were not found to be dependent on substitution. This was because the azomethine fluorescence was found to be quenched relative to their precursors regardless of substitution. The fluorescence could be restored at both low temperature and by acid protonation.

  通过相应的胺和醛芴衍生物之间的简单缩合，制备了一系列芴基氮甲基二元和三元化合物。制备这些化合物是为了研究取代基和电子基团对电化学性质和荧光量子产率的影响。研究发现，通过加入电子捐赠基团和增加共轭程度，可以降低氧化电位。研究还发现，在芴的 9 位上进行烷基化，可迫使所有芴分子与所连接的偶氮甲基键共面，从而提高偶氮甲基键的共轭度。同时，通过用氢原子以外的原子取代末端 2,2′ 位，可实现可逆的自由基阳离子行为。理论上，自由基阳离子均匀地分布在芴中，这证实了 2,2′ 取代后的可逆阳极行为。偶氮甲基的荧光量子产率与取代无关。这是因为无论取代与否，相对于其前体，偶氮甲基荧光都会被淬灭。在低温和酸质子化条件下，荧光都可以恢复。
• Porphyrins with Four Monodisperse Oligofluorene Arms as Efficient Red Light-Emitting Materials
  作者：Binsong Li、Jing Li、Yaqin Fu、Zhishan Bo

  DOI：10.1021/ja039832y

  日期：2004.3.1

  A family of red light-emitting star-shaped porphyrins with four monodisperse conjugated oligofluorene arms was prepared by using two key reactions: Lindsey condensation and Suzuki-Miyaura cross coupling reactions. All porphyrins exhibit high quantum yields (about 0.22) and good solubility in common organic solvents, and form high-quality solid films. Optical studies showed that the star-shaped oligomers

  通过使用两个关键反应：Lindsey 缩合和 Suzuki-Miyaura 交叉偶联反应，制备了一系列具有四个单分散共轭低聚芴臂的红色发光星形卟啉。所有卟啉都表现出高量子产率（约0.22）和在常见有机溶剂中的良好溶解性，并形成高质量的固体薄膜。光学研究表明，星形低聚物可以通过从芴链段到卟啉核的有效能量转移来吸收蓝光并发出饱和红光。