4,4,8,8-tetrabutyl-2,6-diiodopyrazabole | 1192270-02-2

• 英文名称: 4,4,8,8-tetrabutyl-2,6-diiodopyrazabole
• 英文别名: 2,6-diiodopyrazabole；2.6-diiodopyrazabole
• CAS: 1192270-02-2
• 化学式: C₂₂H₄₀B₂I₂N₄
• 分子量: 636.017
• InChiKey: AYCOWUUJAHFDOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  4,4,8,8-tetrabutyl-2,6-diiodopyrazabole 在 bis-triphenylphosphine-palladium(II) chloride diethylamine 、 CuI 、 tetrabutylammonium fluoride 作用下， 以 四氢呋喃 、 二乙胺 为溶剂， 生成 2,6-diethynyl-4,4,8,8-tetrabutylpyrazabole
  参考文献：
  名称：

  含两光子吸收发色团的硼。2.基于吡raz唑的荧光生物探针的一光子和二光子光物理性质的微调

  摘要：

  已经制备了新的含硼的吸收两个光子的荧光团。以吡唑硼烷的核心为中心，研究了各种共轭体系和端基，以调节其理化性质（烷氧基，二苯基氨基和硼二甲基亚甲基）。进行了一个和两个光子的光物理表征，显示出在有机溶剂中有效的荧光。在500-800 nm范围内确定了较高的双光子吸收截面。这些新的含硼荧光生物探针的激光强度在毫瓦范围内，也获得了双光子激发的显微镜图像。

  DOI：

  10.1021/ic900627g
• 作为产物：
  描述：

  4-碘吡唑 、 三丁基硼 以 四氢呋喃 为溶剂， 以70%的产率得到4,4,8,8-tetrabutyl-2,6-diiodopyrazabole
  参考文献：
  名称：

  含两光子吸收发色团的硼。2.基于吡raz唑的荧光生物探针的一光子和二光子光物理性质的微调

  摘要：

  已经制备了新的含硼的吸收两个光子的荧光团。以吡唑硼烷的核心为中心，研究了各种共轭体系和端基，以调节其理化性质（烷氧基，二苯基氨基和硼二甲基亚甲基）。进行了一个和两个光子的光物理表征，显示出在有机溶剂中有效的荧光。在500-800 nm范围内确定了较高的双光子吸收截面。这些新的含硼荧光生物探针的激光强度在毫瓦范围内，也获得了双光子激发的显微镜图像。

  DOI：

  10.1021/ic900627g

文献信息

• Ferrocenyl pyrazaboles: design, synthesis, structure, and properties
  作者：Rajneesh Misra、Thaksen Jadhav、Shaikh M. Mobin

  DOI：10.1039/c3dt52315b

  日期：——

  This article reports the design and synthesis of donor–acceptor–donor type ferrocenyl-substituted pyrazaboles by the Pd-catalyzed Suzuki and Sonogashira coupling reactions. The photophysical and electrochemical behaviors of the ferrocenyl-substituted pyrazaboles were found to be dependent on the nature and length of the spacer groups. The single crystal X-ray structures of ferrocenyl-substituted pyrazaboles 11a, 11b, and 11d were obtained, which reveals that the pyrazabole core exists in chair, planar, and boat conformations. The crystal structures show marvelous supramolecular interactions. The pyrazaboles 11a–11g show good thermal stability, which increases with the length of spacer. The computational study reveals donor–acceptor interactions in ferrocenyl pyrazaboles. The computational results show good agreement with the experimental results.

  本文报告了通过钯催化的铃木和索诺伽希拉偶联反应设计和合成供体-受体-供体型二茂铁取代的吡唑。研究发现二茂铁取代的吡唑的光物理和电化学行为取决于间隔基团的性质和长度。研究人员获得了二茂铁基取代的吡唑 11a、11b 和 11d 的单晶 X 射线结构，发现吡唑核心存在椅状、平面和船状构象。晶体结构显示了奇妙的超分子相互作用。吡唑 11a-11g 显示出良好的热稳定性，并且随着间隔物长度的增加而增加。计算研究揭示了二茂铁吡唑中的供体-受体相互作用。计算结果与实验结果非常吻合。
• Aggregation induced emission and mechanochromism in tetraphenylethene substituted pyrazabole
  作者：Thaksen Jadhav、Bhausaheb Dhokale、Yuvraj patil、Rajneesh Misra

  DOI：10.1039/c5ra12697e

  日期：——

  Tetraphenylethene (TPE) substituted pyrazabole 2 was designed and synthesized by the Pd-catalyzed Suzuki cross-coupling reaction. The pyrazabole exhibits strong aggregation induced emission (AIE) and reversible mechanochromic behavior with high color contrast between blue and green. The powder XRD studies show that destruction of crystalline state into amorphous state is responsible for mechanochromism

  通过Pd催化的Suzuki交叉偶联反应设计并合成了四苯乙烯（TPE）取代的吡唑硼酸酯2。吡唑布拉表现出强的聚集诱导发射（AIE）和可逆的机械变色行为，在蓝色和绿色之间具有高的颜色对比度。粉末XRD研究表明，从晶体状态到无定形状态的破坏是导致机械变色的原因。
• Aryl pyrazaboles: a new class of tunable and highly fluorescent materials
  作者：Rajneesh Misra、Thaksen Jadhav、Shaikh M. Mobin

  DOI：10.1039/c3dt52154k

  日期：——

  Novel aryl substituted pyrazaboles 2–9 with direct and acetylenic linkages were synthesized by Pd-catalyzed Suzuki or Sonogashira cross-coupling reactions. Their structural, thermal, and photonic properties were investigated. The results show that the aryl pyrazaboles 2–9 exhibit good thermal stability, high fluorescence quantum yield, and tunable photophysical properties. The aryl substituted acetylenic pyrazaboles 6–9 exhibit red shifted absorption, small Stokes shifts, and high quantum yields as compared to directly linked aryl pyrazaboles 2–5. The X-ray structures of the pyrazaboles 2, 5, and 7 are discussed. The computational studies were used to calculate the relative energy levels, and band gap in the pyrazaboles. The computational results show good agreement with the experimental results.

  合成了含有直接和炔基连接的芳基取代吡唑碱2–9，采用了Pd催化的铃木或索诺加希拉交叉偶联反应。对其结构、热性质和光学性质进行了研究。结果表明，芳基吡唑碱2–9具有良好的热稳定性、高荧光量子产率和可调的光物理性质。与直接连接的芳基吡唑碱2–5相比，芳基取代的炔基吡唑碱6–9表现出红移的吸收、小斯托克斯位移和高量子产率。讨论了吡唑碱2、5和7的X射线晶体结构。计算研究用于计算吡唑碱中的相对能级和带隙。计算结果与实验结果表现出良好的一致性。
• Design and synthesis of donor–acceptor pyrazabole derivatives for multiphoton absorption
  作者：Thaksen Jadhav、Ramesh Maragani、Rajneesh Misra、V. Sreeramulu、D. Narayana Rao、Shaikh M. Mobin

  DOI：10.1039/c3dt33065f

  日期：——

  A series of ferrocenyl substituted pyrazaboles were prepared, which have an electron-withdrawing pyrazabole moiety as the central core, with a D–π–A–π–D structural motif (D = donor, A = acceptor) and containing a variety of π bridges. A crystallographic study reveals that the pyrazabole central core was observed in planar geometry. Strong two-photon absorption in the visible region and three-photon absorption in the near IR region were observed in the ferrocenyl substituted pyrazaboles. It was observed that the 2PA absorption cross-section increases with the conjugation length.

  一系列铁氟烯基取代的吡唑并咪唑被制备，这些化合物的中心核心是一个具有电子吸引特性的吡唑并咪唑部分，采用 D–π–A–π–D 结构构型（D = 供体，A = 受体），并包含多种 π 桥。晶体学研究表明，吡唑并咪唑的中心核心呈现平面几何形状。在可见光区域观察到强的双光子吸收，而在近红外区域观察到三光子吸收。结果表明，双光子吸收截面随共轭长度的增加而增加。