2,5-bis(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)-1,3,4-oxadiazole | 1246171-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,5-bis(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)-1,3,4-oxadiazole
• 英文别名: 2,5-Bis(7-bromo-9,9-dihexylfluoren-2-yl)-1,3,4-oxadiazole
• CAS: 1246171-20-9
• 化学式: C₅₂H₆₄Br₂N₂O
• 分子量: 892.901
• InChiKey: GPPYLQIJVDBXTC-UHFFFAOYSA-N

物化性质

• 沸点：
  863.2±75.0 °C(predicted)
• 密度：
  1.189±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  20.3
• 重原子数：
  57
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)-1,3,4-oxadiazole 在 甲醇 、 copper(l) iodide 、 palladium diacetate 、 potassium carbonate 、 二异丙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 2,5-Bis(7-ethynyl-9,9-dihexylfluoren-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, Light-Emitting, and Two-Photon Absorption Properties of Platinum-Containing Poly(arylene-ethynylene)s Linked by 1,3,4-Oxadiazole Units

  摘要：

  A series of soluble and thermally stable group 10 platinum(II) polyyne polymers of the type [-C equivalent to C- P1(PBu3)(2)-C equivalent to C-Ar-Ox-Ar-](n) (where Ox = 1,3,4-oxadiazole, Ar = p-C6H4 or 2,7-dihexy]-9.9-fluorene) and [-C equivalent to C-Pt(PBu3)(2)-C equivalent to C-Ar-Ox-Ar-Ox-Ar](n) (where Ar = 2,7-dihexy]-9.9-fluorene) along with their corresponding dinuclear model compounds [Ph-P1(PEt3)(2)-C equivalent to C-Ar-l(2)-Ox-(where Ar = p-C6H4 or 2,7-dihexy1-9,9-fluorene) and [Ph-Pt(PEt3)(2)-C equivalent to C-Ar-Ox-](2)-Ar- (where Ar = 2,7-dihexyl-9,9-fluorene) were prepared and characterized. The regiochemical structure of the polymers has been ascertained by single-crystal X-ray analysis on the model compound [Ph-Pt(PEt3)(2)-C equivalent to C-p-C6H4-l(2)-Ox- The photophysical properties (absorption, excitation, emission, and nanosecond transient absorption spectra) of these metalated compounds in 2MeTHF at 298 and 77 K are reported. These findings are correlated by density functional theory (DFT) calculations. Geometry optimizations predict totally planar molecules for these metalated complexes and polymers, allowing better pi-conjugation across the main chain. The ligands are strongly fluorescent but become also phosphorescent when the Pt atom is introduced in the backbone of the conjugated organometa Hie complexes and polymers. These emissions arc assigned to pi pi* transitions in all cases involving the Ptd(xy) orbitals. These Pt compounds exhibit two-photon absorption (2PA), and their 2PA cross sections (sigma 2) have been determined. The potential of exploiting such metallopolymers for the design of electrophosphorescent polymer light-emitting devices (PLEDs) and their use as single-dopant for white PLEDs have also been discussed.

  DOI：

  10.1021/ma1009319
• 作为产物：
  描述：

  9,9-二己基-2,7-二溴代芴 在 吡啶 、 N-甲基吡咯烷酮 、 氯化亚砜 、 硫酸 、 盐酸羟胺 、 溶剂黄146 、 三氯氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 2,5-bis(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  具有对称和不对称取代骨架的小树枝状发色团的合成和双光子特性

  摘要：

  一组新型多支化发色团由两组芴/恶二唑类类似物组成，具有供体-π-受体（不对称）和供体-π-受体-π-供体（对称）类型的通用骨架已被合成并显示在飞秒激光脉冲照射下，在近红外 (NIR) 区域显示强且广泛分散的双光子吸收率。还证明了结构参数，例如连接的供体单元的数量和取代模式，与这些模型化合物的分子双光子活性密切相关。

  DOI：

  10.1002/ejoc.201101485

文献信息

• Multi-photon properties of branched chromophores derived from indenoquinoxaline and oxadiazole heterocyclic units
  作者：Tzu-Chau Lin、Shih-Huang Chang、Hsiang-Yu Hsieh、Zi-Ming Chen、Chun-Yao Chu

  DOI：10.1039/d0ra08945a

  日期：——

  Multi-branched chromophores derived from indenoquinoxaline and oxadiazole units were developed to possess strong two- and three-photon activities in the NIR-region.

  从吲哚并并[1,2-c:3,4-c']二氮杂基和噁唑啉单元衍生出的多分支色团被开发出来，具有在近红外区域强烈的二光子和三光子活性。
• Synthesis and Two-Photon Properties of Small Dendritic Chromophores with Symmetrical and Unsymmetrical Substituted Skeletons
  作者：Tzu-Chau Lin、Ying-Hsuan Lee、Chia-Ling Hu、Yu-Kai Li、Yu-Jhen Huang

  DOI：10.1002/ejoc.201101485

  日期：2012.3

  A set of novel multi-branched chromophores consisting of two groups of fluorene/oxadiazole-based analogues with generic skeletons of donor-π-acceptor (unsymmetrical) and donor-π-acceptor-π-donor (symmetrical) type has been synthesized and shown to display strong and broadly dispersed two-photon absorptivities in the near infrared (NIR) region on irradiation with femtosecond laser pulses. It is also

  一组新型多支化发色团由两组芴/恶二唑类类似物组成，具有供体-π-受体（不对称）和供体-π-受体-π-供体（对称）类型的通用骨架已被合成并显示在飞秒激光脉冲照射下，在近红外 (NIR) 区域显示强且广泛分散的双光子吸收率。还证明了结构参数，例如连接的供体单元的数量和取代模式，与这些模型化合物的分子双光子活性密切相关。
• Synthesis, Light-Emitting, and Two-Photon Absorption Properties of Platinum-Containing Poly(arylene-ethynylene)s Linked by 1,3,4-Oxadiazole Units
  作者：Thomas Goudreault、Ze He、Yanhe Guo、Cheuk-Lam Ho、Hongmei Zhan、Qiwei Wang、Keith Yat-Fung Ho、Ka-Leung Wong、Daniel Fortin、Bing Yao、Zhiyuan Xie、Lixiang Wang、Wai-Ming Kwok、Pierre D. Harvey、Wai-Yeung Wong

  DOI：10.1021/ma1009319

  日期：2010.10.12

  A series of soluble and thermally stable group 10 platinum(II) polyyne polymers of the type [-C equivalent to C- P1(PBu3)(2)-C equivalent to C-Ar-Ox-Ar-](n) (where Ox = 1,3,4-oxadiazole, Ar = p-C6H4 or 2,7-dihexy]-9.9-fluorene) and [-C equivalent to C-Pt(PBu3)(2)-C equivalent to C-Ar-Ox-Ar-Ox-Ar](n) (where Ar = 2,7-dihexy]-9.9-fluorene) along with their corresponding dinuclear model compounds [Ph-P1(PEt3)(2)-C equivalent to C-Ar-l(2)-Ox-(where Ar = p-C6H4 or 2,7-dihexy1-9,9-fluorene) and [Ph-Pt(PEt3)(2)-C equivalent to C-Ar-Ox-](2)-Ar- (where Ar = 2,7-dihexyl-9,9-fluorene) were prepared and characterized. The regiochemical structure of the polymers has been ascertained by single-crystal X-ray analysis on the model compound [Ph-Pt(PEt3)(2)-C equivalent to C-p-C6H4-l(2)-Ox- The photophysical properties (absorption, excitation, emission, and nanosecond transient absorption spectra) of these metalated compounds in 2MeTHF at 298 and 77 K are reported. These findings are correlated by density functional theory (DFT) calculations. Geometry optimizations predict totally planar molecules for these metalated complexes and polymers, allowing better pi-conjugation across the main chain. The ligands are strongly fluorescent but become also phosphorescent when the Pt atom is introduced in the backbone of the conjugated organometa Hie complexes and polymers. These emissions arc assigned to pi pi* transitions in all cases involving the Ptd(xy) orbitals. These Pt compounds exhibit two-photon absorption (2PA), and their 2PA cross sections (sigma 2) have been determined. The potential of exploiting such metallopolymers for the design of electrophosphorescent polymer light-emitting devices (PLEDs) and their use as single-dopant for white PLEDs have also been discussed.