2,8-bis-(8-ethynyl-dibenzothiophen-2-ylethynyl)-dibenzothiophene 5,5-dioxide | 959929-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,8-bis-(8-ethynyl-dibenzothiophen-2-ylethynyl)-dibenzothiophene 5,5-dioxide
• 英文别名: 2,8-Bis[2-(8-ethynyldibenzothiophen-2-yl)ethynyl]dibenzothiophene 5,5-dioxide
• CAS: 959929-47-6
• 化学式: C₄₄H₂₀O₂S₃
• 分子量: 676.84
• InChiKey: GGZVSWKOYIBPHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  49
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{4-[2-(2-butoxy-ethoxy)-ethoxy]-phenylethynyl}-8-iodo-dibenzothiophene 5,5-dioxide 、 2,8-bis-(8-ethynyl-dibenzothiophen-2-ylethynyl)-dibenzothiophene 5,5-dioxide 在 palladium dichloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以22%的产率得到2-[2-[4-[2-(2-Butoxyethoxy)ethoxy]phenyl]ethynyl]-8-[2-[8-[2-[8-[2-[8-[2-[8-[2-[4-[2-(2-butoxyethoxy)ethoxy]phenyl]ethynyl]-5,5-dioxodibenzothiophen-2-yl]ethynyl]dibenzothiophen-2-yl]ethynyl]-5,5-dioxodibenzothiophen-2-yl]ethynyl]dibenzothiophen-2-yl]ethynyl]dibenzothiophene 5,5-dioxide
  参考文献：
  名称：

  Synthesis and Structure-Linear and Structure-Nonlinear Optical Properties of Multi-Dipolar Zigzag Oligoaryleneethynylenes

  摘要：

  A novel series of monodisperse, multi-dipolar zigzag oligoaryleneethynylenes DA(n) and D-Ar-A(n), bearing electron-donating dibenzothiophene and electron-accepting dibenzothiophene dioxide as arenes, with up to six charge-transfer (dipolar) units have been designed and synthesized by palladium-catalyzed Sonogashira coupling reactions. The linear and nonlinear optical properties of these multi-dipolar oligoaryleneethynylenes can easily be modified or enhanced by incorporating/extending with various central aryleneethynyl moieties such as phenylethynyl, oligo(9,9-dibutylfluorenyl)ethynyl, and oligothienylethynyl within the donor-acceptor units. Interestingly, the absorption and emission of these zigzag oligoaryleneethynylenes are not dependent on the number of covalently linked dipolar chromophores; however, the fluorescence quantum efficiencies consistently decrease with increased number of covalently linked dipolar units. These zigzag oligoaryleneethynylenes exhibit a linear increase in the two-photon absorption (TPA) cross-sections with increased number of covalently linked dipolar units without red-shifting the absorption and emission spectra. In addition, very large TPA cross-sections in the femtosecond regime (sigma(800) = 1306 GM in DMF or sigma(750) = 1522 GM in CH2Cl2) were obtained for D-TF-A(4) despite the moderate strength of the donor-acceptor pair. Our results suggest that the TPA properties of these zigzag oligoaryleneethynylenes including TPA wavelength and TPA cross-section can easily be tuned by means of modifying the central aryleneethynylene units and increasing the number of dipolar units, respectively. This approach provides an alternative means to tune or enhance the TPA cross-section at a specific wavelength.

  DOI：

  10.1021/jo070607z
• 作为产物：
  描述：

  2,8-bis[(trimethylsilyl)ethynyl]dibenzothiophene 在 palladium dichloride 甲醇 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 2,8-bis-(8-ethynyl-dibenzothiophen-2-ylethynyl)-dibenzothiophene 5,5-dioxide
  参考文献：
  名称：

  Synthesis and Structure-Linear and Structure-Nonlinear Optical Properties of Multi-Dipolar Zigzag Oligoaryleneethynylenes

  摘要：

  A novel series of monodisperse, multi-dipolar zigzag oligoaryleneethynylenes DA(n) and D-Ar-A(n), bearing electron-donating dibenzothiophene and electron-accepting dibenzothiophene dioxide as arenes, with up to six charge-transfer (dipolar) units have been designed and synthesized by palladium-catalyzed Sonogashira coupling reactions. The linear and nonlinear optical properties of these multi-dipolar oligoaryleneethynylenes can easily be modified or enhanced by incorporating/extending with various central aryleneethynyl moieties such as phenylethynyl, oligo(9,9-dibutylfluorenyl)ethynyl, and oligothienylethynyl within the donor-acceptor units. Interestingly, the absorption and emission of these zigzag oligoaryleneethynylenes are not dependent on the number of covalently linked dipolar chromophores; however, the fluorescence quantum efficiencies consistently decrease with increased number of covalently linked dipolar units. These zigzag oligoaryleneethynylenes exhibit a linear increase in the two-photon absorption (TPA) cross-sections with increased number of covalently linked dipolar units without red-shifting the absorption and emission spectra. In addition, very large TPA cross-sections in the femtosecond regime (sigma(800) = 1306 GM in DMF or sigma(750) = 1522 GM in CH2Cl2) were obtained for D-TF-A(4) despite the moderate strength of the donor-acceptor pair. Our results suggest that the TPA properties of these zigzag oligoaryleneethynylenes including TPA wavelength and TPA cross-section can easily be tuned by means of modifying the central aryleneethynylene units and increasing the number of dipolar units, respectively. This approach provides an alternative means to tune or enhance the TPA cross-section at a specific wavelength.

  DOI：

  10.1021/jo070607z

文献信息

• Synthesis and Structure-Linear and Structure-Nonlinear Optical Properties of Multi-Dipolar Zigzag Oligoaryleneethynylenes
  作者：Pik Kwan Lo、King Fai Li、Man Shing Wong、Kok Wai Cheah

  DOI：10.1021/jo070607z

  日期：2007.8.31

  A novel series of monodisperse, multi-dipolar zigzag oligoaryleneethynylenes DA(n) and D-Ar-A(n), bearing electron-donating dibenzothiophene and electron-accepting dibenzothiophene dioxide as arenes, with up to six charge-transfer (dipolar) units have been designed and synthesized by palladium-catalyzed Sonogashira coupling reactions. The linear and nonlinear optical properties of these multi-dipolar oligoaryleneethynylenes can easily be modified or enhanced by incorporating/extending with various central aryleneethynyl moieties such as phenylethynyl, oligo(9,9-dibutylfluorenyl)ethynyl, and oligothienylethynyl within the donor-acceptor units. Interestingly, the absorption and emission of these zigzag oligoaryleneethynylenes are not dependent on the number of covalently linked dipolar chromophores; however, the fluorescence quantum efficiencies consistently decrease with increased number of covalently linked dipolar units. These zigzag oligoaryleneethynylenes exhibit a linear increase in the two-photon absorption (TPA) cross-sections with increased number of covalently linked dipolar units without red-shifting the absorption and emission spectra. In addition, very large TPA cross-sections in the femtosecond regime (sigma(800) = 1306 GM in DMF or sigma(750) = 1522 GM in CH2Cl2) were obtained for D-TF-A(4) despite the moderate strength of the donor-acceptor pair. Our results suggest that the TPA properties of these zigzag oligoaryleneethynylenes including TPA wavelength and TPA cross-section can easily be tuned by means of modifying the central aryleneethynylene units and increasing the number of dipolar units, respectively. This approach provides an alternative means to tune or enhance the TPA cross-section at a specific wavelength.