3,5-bis[2'-4(dibuthylaminophenyl)vinyl]benzaldehyde | 348621-30-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3,5-bis[2'-4(dibuthylaminophenyl)vinyl]benzaldehyde
• 英文别名: 3,5-bis(p-dibutylaminostyryl)benzaldehyde；3,5-bis[(E)-2-[4-(dibutylamino)phenyl]ethenyl]benzaldehyde
• CAS: 348621-30-7
• 化学式: C₃₉H₅₂N₂O
• 分子量: 564.855
• InChiKey: UWJWYBOEVUUOOX-WXUKJITCSA-N

物化性质

• 熔点：
  60-63 °C(Solvent: Hexane; Dichloromethane)
• 沸点：
  713.6±60.0 °C(predicted)
• 密度：
  1.042±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  42
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-bis[2'-4(dibuthylaminophenyl)vinyl]benzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 3,5-bis{2'[3,5-bis[2'-(4-dibutylaminophenyl)vinyl]]}benzaldehyde
  参考文献：
  名称：

  偶极和非偶极聚（亚苯基亚乙烯基）树状聚合物的合成，表征和光学响应。

  摘要：

  使用Heck和Horner-Wadsworth-Emmons反应已有效地合成了带有供电子基团和吸电子基团的新型偶极和非偶极聚（亚苯基亚乙烯基）树状聚合物。这些系统的光致发光可通过选择适当的外围基团在蓝色区域进行调节。尽管有亚取代模式，但当pi供体基团和pi受体基团通过间亚苯基亚乙烯基系统连接时，仍可观察到较大的斯托克斯位移。

  DOI：

  10.1021/jo015764r
• 作为产物：
  描述：

  3,5-二甲基苯腈 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium tert-butylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 3,5-bis[2'-4(dibuthylaminophenyl)vinyl]benzaldehyde
  参考文献：
  名称：

  Rigid Dendritic Donor−Acceptor Ensembles:  Control over Energy and Electron Transduction

  摘要：

  Several generations of phenylenevinylene dendrons, covalently attached to a C-60 core, have been developed as synthetic model systems with hierarchical, fine-tuned architectures. End-capping of these dendritic spacers with dibutylaniline or dodecyloxynaphthalene, as antennas/electron donors, yielded new donor-bridge-acceptor ensembles in which one, two, or four donors are allocated at the peripheral positions of the well-defined dendrons, while the electron accepting fullerene is placed at the focal point of the dendron. On the basis of our cyclic voltammetry experiments, which disclose a single anodic oxidation and several cathodic reduction processes, we rule out significant, long-range couplings between the fullerene core and the end-standing donors in their ground-state configuration. Photophysical investigations, on the other hand, show that upon photoexcitation an efficient and rapid transfer of singlet excited-state energy (6 x 10(10) to 2.5 N 10(12) s(-1)) controls the reactivity of the initially excited antenna portion. Spectroscopic and kinetic evidence suggests that yet a second contribution, that is, an intramolecular electron-transfer, exists, affording C-60(.-) -dendron(.+) with quantum yields (Phi) as high as 0.76 and lifetimes (tau) that are on the order of hundreds of nanoseconds (220-725 ns). Variation of the energy gap modulates the interplay of these two pathways (i.e., competition or sequence between energy and electron transfer).

  DOI：

  10.1021/ja012694x

文献信息

• Synthesis of Photo- and Electroactive Stilbenoid Dendrimers Carrying Dibutylamino Peripheral Groups
  作者：José L. Segura、Rafael Gómez、Nazario Martín、Dirk M. Guldi

  DOI：10.1021/ol016083l

  日期：2001.8.1

  [structure: see text]. A novel convergent synthetic route for the preparation of functionalized and fluorescent stilbenoid dendrons built on the 1,3,5-benzene core and endowed with a periphery of dibutylamino groups has been developed. Long alkyl chains have been incorporated on the peripheral amino moieties to increase the solubility of the final products. Good donor ability of the new dendrimers

  [结构：见文字]。开发了一种新的聚合合成路线，用于制备功能化的和荧光的二苯乙烯类树突，其建立在1,3,5-苯核上并具有二丁基氨基外围。长烷基链已结合在外围氨基部分上以增加最终产物的溶解度。由于存在外围二丁基苯胺部分，通过循环伏安法测量已观察到新的树枝状聚合物的良好供体能力。
• Comparison between the Photophysical Properties of Pyrazolo- and Isoxazolo[60]fullerenes with Dual Donors (Ferrocene, Aniline and Alkoxyphenyl)
  作者：Laura Perez、Mohamed E. El-Khouly、Pilar de la Cruz、Yasuyuki Araki、Osamu Ito、Fernando Langa

  DOI：10.1002/ejoc.200600921

  日期：2007.5

  Two series of new pyrazolo- and isoxazolo[60]fullerenes covalently linked to vinylenephenylene bearing ferrocene, dibutylaniline or dodecyloxyphenyl electron-donor groups attached in the periphery have been synthesized. The photophysical properties of these newly synthesized dual-donor–C60 derivatives have been investigated and compared by applying time-resolved fluorescence and nanosecond transient

  已经合成了两个系列的新型吡唑并和异恶唑并 [60] 富勒烯，它们与亚乙烯基亚苯基共价连接，在外围连接有二茂铁、二丁基苯胺或十二烷氧基苯基电子给体基团。通过在极性和非极性溶剂中应用时间分辨荧光和纳秒瞬态技术，研究和比较了这些新合成的双供体 C60 衍生物的光物理性质。通过 C60 的激发单线态进行电荷分离在吡唑并 C60 三元组中比在异恶唑并 C60 三元组中更有效。发现由于吡唑啉环的氮原子与异恶唑啉环的氧原子相比更强的给电子特性，吡唑啉环介导电荷分离。(© Wiley-VCH Verlag GmbH & Co. KGaA,
• Synthesis and Photoluminescent Properties of 1,1‘-Binaphthyl-Based Chiral Phenylenevinylene Dendrimers
  作者：Enrique Díez-Barra、Joaquín C. García-Martínez、Riánsares del Rey、Julián Rodríguez-López、Francesco Giacalone、José L. Segura、Nazario Martín

  DOI：10.1021/jo026222s

  日期：2003.4.1

  New chiral, soluble binaphthyl derivatives that incorporate stilbenoid dendrons at the 6,6'-positions have been prepared. The synthesis of the new enantiopure dendrimers was performed in a convergent manner by Horner-Wadsworth-Emmons (HWE) reaction of the appropriately functionalized 1,1'-binaphthyl derivative (R)-1 and the appropriate dendrons (R)(2n)G(n)-CHO. Different electroactive units were incorporated in the peripheral positions of the dendrons in order to tune both the optical and electrochemical behavior of these systems. Fluorescence measurements on the chiral dendrimers reveal a strong emission with maxima between 409 and 508 nm depending upon the substitution pattern. Finally, the redox properties of the dendrimers were determined by cyclic voltammetry, showing the influence of the functional groups at the peripheral positions of the dendrimer on the redox behavior of these systems.
• Rigid Dendritic Donor−Acceptor Ensembles:  Control over Energy and Electron Transduction
  作者：Dirk M. Guldi、Angela Swartz、Chuping Luo、Rafael Gómez、José L. Segura、Nazario Martín

  DOI：10.1021/ja012694x

  日期：2002.9.1

  Several generations of phenylenevinylene dendrons, covalently attached to a C-60 core, have been developed as synthetic model systems with hierarchical, fine-tuned architectures. End-capping of these dendritic spacers with dibutylaniline or dodecyloxynaphthalene, as antennas/electron donors, yielded new donor-bridge-acceptor ensembles in which one, two, or four donors are allocated at the peripheral positions of the well-defined dendrons, while the electron accepting fullerene is placed at the focal point of the dendron. On the basis of our cyclic voltammetry experiments, which disclose a single anodic oxidation and several cathodic reduction processes, we rule out significant, long-range couplings between the fullerene core and the end-standing donors in their ground-state configuration. Photophysical investigations, on the other hand, show that upon photoexcitation an efficient and rapid transfer of singlet excited-state energy (6 x 10(10) to 2.5 N 10(12) s(-1)) controls the reactivity of the initially excited antenna portion. Spectroscopic and kinetic evidence suggests that yet a second contribution, that is, an intramolecular electron-transfer, exists, affording C-60(.-) -dendron(.+) with quantum yields (Phi) as high as 0.76 and lifetimes (tau) that are on the order of hundreds of nanoseconds (220-725 ns). Variation of the energy gap modulates the interplay of these two pathways (i.e., competition or sequence between energy and electron transfer).
• Synthesis, Characterization, and Optical Response of Dipolar and Non-Dipolar Poly(phenylenevinylene) Dendrimers
  作者：Enrique Díez-Barra、Joaquín C. García-Martínez、Sonia Merino、Riánsares del Rey、Julián Rodríguez-López、Prado Sánchez-Verdú、Juan Tejeda

  DOI：10.1021/jo015764r

  日期：2001.8.1

  New dipolar and non-dipolar poly(phenylenevinylene) dendrimers bearing electron-donating and electron-withdrawing groups have been efficiently synthesized using Heck and Horner-Wadsworth-Emmons reactions. The photoluminescence of these systems may be tuned in the blue zone by choosing the appropriate peripheral groups. Despite the meta-substitution pattern, large Stokes shifts can be observed when

  使用Heck和Horner-Wadsworth-Emmons反应已有效地合成了带有供电子基团和吸电子基团的新型偶极和非偶极聚（亚苯基亚乙烯基）树状聚合物。这些系统的光致发光可通过选择适当的外围基团在蓝色区域进行调节。尽管有亚取代模式，但当pi供体基团和pi受体基团通过间亚苯基亚乙烯基系统连接时，仍可观察到较大的斯托克斯位移。