(3,3'-dihexyl-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) | 869556-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: (3,3'-dihexyl-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)
• 英文别名: 5,5'-bis(trimethylstannyl)-3,3'-dihexyl-2,2'-bithiophene；Agn-PC-00btgf；[4-hexyl-5-(3-hexyl-5-trimethylstannylthiophen-2-yl)thiophen-2-yl]-trimethylstannane
• CAS: 869556-90-1
• 化学式: C₂₆H₄₆S₂Sn₂
• 分子量: 660.203
• InChiKey: PUEXQLSQBSOSKB-UHFFFAOYSA-N

物化性质

• 沸点：
  579.0±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.81
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3,3'-dihexyl-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane) 、 pentafluorophenyldibromoborane 以 二氯甲烷 为溶剂， 生成 PTh-BPf
  参考文献：
  名称：

  A Family of Main-Chain Polymeric Lewis Acids:  Synthesis and Fluorescent Sensing Properties of Boron-Modified Polythiophenes

  摘要：

  A new family of main-chain organoborane polymeric Lewis acids (PTh-BAr) that contain Lewis acidic boron groups embedded into a polythiophene backbone has been prepared under mild conditions through tin-boron exchange reaction. When phenyl and pentafluorophenyl groups are attached to boron, blue and green luminescence is observed, respectively, while the attachment of ferrocenyl substituents leads to a characteristic red color. The incorporation of readily accessible highly Lewis acidic groups into the conjugated polymer backbone provides an opportunity for sensing of Lewis basic substrates. For instance, treatment of the polymer containing phenyl substituents on boron with pyridine leads to efficient quenching of the fluorescence, while the polymer containing ferrocenyl groups changes color from dark red to light orange.

  DOI：

  10.1021/ja0537880
• 作为产物：
  描述：

  三甲基氯化锡 、 3,3'-二己基-2,2'-并噻吩 在 正丁基锂 作用下， 反应 1.0h， 生成 (3,3'-dihexyl-[2,2'-bithiophene]-5,5'-diyl)bis(trimethylstannane)
  参考文献：
  名称：

  基于6,7-二氯喹喔啉的高效深红色电致发光供体-受体共聚物

  摘要：

  由于氯原子引起的大位阻不仅抑制了聚集，而且还导致了较大的斯托克斯位移和低的自吸收性，因此，通过改变甲壳素的结构，合成了一系列基于6,7-二氯喹喔啉的供体-受体交替共聚物。寡聚噻吩。所有聚合物均已被很好地表征，以研究寡聚噻吩的长度和位阻对光学，电子和电致发光性质的影响。观察到分子内的电荷转移吸收由于位阻而减弱。与非氯化物类似物不同，给定相似的空间位阻，延长的共轭长度会导致较小的带隙。以678 nm为中心的深红色发射，亮度约为1800 cd m -2 使用掺杂剂/主体技术以1.34％的外部量子效率实现了这一目标。

  DOI：

  10.1016/j.orgel.2017.04.002

文献信息

• Conjugated Oligomers with Stable Radical Substituents: Synthesis, Single Crystal Structures, Electronic Structure, and Excited State Dynamics
  作者：Yiming Huang、Zihao Xu、Shijian Jin、Chenyang Li、Kurt Warncke、Francesco A. Evangelista、Tianquan Lian、Eilaf Egap

  DOI：10.1021/acs.chemmater.8b03366

  日期：2018.11.13

  joint experimental and computational study elucidating excited-state dynamics and kinetics of oligothiophenes covalently linked to two radicals. The synthesis, steady-state, and ultrafast photophysics, magnetic properties, computational modeling, and single crystal X-ray diffraction of a series of oligothiophenes with appended nitronyl nitroxide (NN) diradicals (RAx and RBx) are presented. We show that

  了解和控制有机半导体中的自旋动力学具有重大的技术意义。我们提出了一项全面的联合实验和计算研究，阐明了与两个自由基共价连接的低聚噻吩的激发态动力学和动力学。一系列低聚噻吩并附有亚硝酰氮氧化物（NN）双自由基（RAx和RBx）的合成，稳态和超快光物理性质，磁性，计算模型和单晶X射线衍射）。我们表明，引入双基自由基会导致令人感兴趣的分子堆积，令人联想到有机笼，异常的激发态动力学以及有趣的光物理和磁特性。我们发现双自由基环和寡噻吩核之间的距离和二面角的增加导致弱的反铁磁相互作用。单晶X射线衍射和计算模型表明，沿着主链的有效共轭导致有效的自旋极化转移。插入p-将亚苯基噻吩核心与NN自由基组分平均隔开4.3Å的亚苯基接头导致生色团和两个NN自由基单独占据的分子轨道之间的轨道重叠减少，并且沿噻吩核心的自旋极化弱。计算还预测了一个双自由基基态，其单重态-三重态能隙（ΔE ST）为0.6 kcal / mo
• Topological Transformation of π‐Conjugated Molecules Reduces Resistance to Crystallization
  作者：Cheng Zhou、Qiuhong Cui、Caitlin McDowell、Martin Seifrid、Xiankai Chen、Jean‐Luc Brédas、Ming Wang、Fei Huang、Guillermo C. Bazan

  DOI：10.1002/anie.201702646

  日期：2017.8

  form crystals in which the molecular shape is significantly more planar. Two thermally reversible polymorphs for TT were observed by XRD and grazing-incidence wide-angle X-ray scattering (GIWAXS) measurements. These findings are relevant within the context of designing soft semiconductors that exhibit high solubility and a tendency to provide stable organized structures with desirable electronic properties

  设计两个电子离域分子作为模型，以了解分子形状如何影响分子半导体中溶解度和结晶趋势之间的权衡。溶解度更高的化合物TT包含一个非平面的联噻吩中心片段，而CT则具有一个平面的环戊二噻吩单元。量热研究显示，CT比TT更容易结晶。但是，吸收光谱法显示，最初的非晶态TT膜最终可以形成分子形状明显更平坦的晶体。TT的两种热可逆多晶型通过XRD和掠入射广角X射线散射（GIWAXS）测量来观察。这些发现在设计软半导体的背景下是有意义的，所述软半导体表现出高溶解度并且倾向于提供具有期望的电子性质的稳定的有组织的结构。
• A Family of Main-Chain Polymeric Lewis Acids:  Synthesis and Fluorescent Sensing Properties of Boron-Modified Polythiophenes
  作者：Anand Sundararaman、Maria Victor、Resmi Varughese、Frieder Jäkle

  DOI：10.1021/ja0537880

  日期：2005.10.1

  A new family of main-chain organoborane polymeric Lewis acids (PTh-BAr) that contain Lewis acidic boron groups embedded into a polythiophene backbone has been prepared under mild conditions through tin-boron exchange reaction. When phenyl and pentafluorophenyl groups are attached to boron, blue and green luminescence is observed, respectively, while the attachment of ferrocenyl substituents leads to a characteristic red color. The incorporation of readily accessible highly Lewis acidic groups into the conjugated polymer backbone provides an opportunity for sensing of Lewis basic substrates. For instance, treatment of the polymer containing phenyl substituents on boron with pyridine leads to efficient quenching of the fluorescence, while the polymer containing ferrocenyl groups changes color from dark red to light orange.
• Efficient deep-red electroluminescent donor-acceptor copolymers based on 6,7-dichloroquinoxaline
  作者：Xiang Gao、Yubao Zhang、Cheng Fang、Xiang Cai、Bin Hu、Guoli Tu

  DOI：10.1016/j.orgel.2017.04.002

  日期：2017.7

  Since the large steric hindrance caused by chlorine atoms not only suppresses the aggregation but also results in large stokes shift and low self-absorption, a series of donor-acceptor alternating copolymers based on 6,7-dichloroquinoxaline have been synthesized by modifying the structures of oligothiophenes. All the polymers have been well characterized to study the effects of the length of oligothiophenes

  由于氯原子引起的大位阻不仅抑制了聚集，而且还导致了较大的斯托克斯位移和低的自吸收性，因此，通过改变甲壳素的结构，合成了一系列基于6,7-二氯喹喔啉的供体-受体交替共聚物。寡聚噻吩。所有聚合物均已被很好地表征，以研究寡聚噻吩的长度和位阻对光学，电子和电致发光性质的影响。观察到分子内的电荷转移吸收由于位阻而减弱。与非氯化物类似物不同，给定相似的空间位阻，延长的共轭长度会导致较小的带隙。以678 nm为中心的深红色发射，亮度约为1800 cd m -2 使用掺杂剂/主体技术以1.34％的外部量子效率实现了这一目标。