2-(2,2'-bithien-5-yl)-2-hexyl-1,3-dioxolane

• 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: 2-(2,2'-bithien-5-yl)-2-hexyl-1,3-dioxolane
• 英文别名: 2-[5-[5-(2-Hexyl-1,3-dioxolan-2-yl)thiophen-2-yl]thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 化学式: C₂₃H₃₃BO₄S₂
• 分子量: 448.456
• InChiKey: MXELTACJDOMFKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,2'-bithien-5-yl)-2-hexyl-1,3-dioxolane 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 16.0h， 生成 1,1'-[(4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6-diyl)bis(2,2'-bithiene-5',5-diyl)]diheptan-1-one
  参考文献：
  名称：

  Effects of bridging atom and π-bridge length on physical and photovoltaic properties of A–π-D–π-A oligomers for solution-processed organic solar cells

  摘要：

  Synthesis of novel acceptor-donor-acceptor oligomers with electron-withdrawing alkyldicyanovinyl groups linked through an oligothiophene pi-bridge with either dithienosilole or cyclopentadithiophene electron donor units is described. Changing the bridgehead atom from carbon to silicon in the central donor unit leads to a significant change in optical, thermal and structural properties of the oligomers. In addition, elongation of the oligothiophene pi-bridge in the oligomers increases energies of HOMO and LUMO levels and leads to an unexpected hypsochromic shift of their absorption spectrum, because extension of the conjugation length cannot compensate a decrease of the intramolecular charge transfer between the dithienosilole and dicyanovinyl units. Although these minor changes in the chemical structures have a pronounced impact on the morphologies of their blends with PC70BM, the optimized solution-processed organic solar cells based on these small molecules demonstrate similar power conversion efficiencies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.06.026
• 作为产物：
  描述：

  庚酰氯 在 正丁基锂 、 对甲苯磺酸 、 magnesium 作用下， 以 正己烷 、 苯 为溶剂， 生成 2-(2,2'-bithien-5-yl)-2-hexyl-1,3-dioxolane
  参考文献：
  名称：

  Effects of oligothiophene π-bridge length on physical and photovoltaic properties of star-shaped molecules for bulk heterojunction solar cells

  摘要：

  本文报道了四种不同星形供体（D）——受体（A）小分子（N（Ph-1T-DCN-Me）3、N（Ph-2T-DCN-Me）3、N（Ph-2T-DCN-Hex）3和N（Ph-3T-DCN-Hex）3）的制备，这些小分子具有不同的噻吩-桥长度，并用于溶液加工的体异质结小分子太阳能电池。光学和电化学数据表明，噻吩-桥长度的增加会导致光带隙的减小，这是由于最高被占分子轨道（HOMO）水平的平行增加。此外，分子-桥长度的细微变化会强烈影响热性能、溶解度、结晶、薄膜形态和电荷载流子迁移率，进而显著改变器件性能。虽然适度增加噻吩-桥长度会提升HOMO水平，但由于短路电流（Jsc）和填充因子（FF）同时提高，它仍然可以提高太阳能电池的效率。该研究表明，这种方法可以成为有效调节有机太阳能电池（OSC）的光电性能的有趣工具，且成本适中。

  DOI：

  10.1039/c4ta01933d

文献信息

• Effects of oligothiophene π-bridge length on physical and photovoltaic properties of star-shaped molecules for bulk heterojunction solar cells
  作者：Jie Min、Yuriy N. Luponosov、Derya Baran、Sergei N. Chvalun、Maxim A. Shcherbina、Artem V. Bakirov、Petr V. Dmitryakov、Svetlana M. Peregudova、Nina Kausch-Busies、Sergei A. Ponomarenko、Tayebeh Ameri、Christoph J. Brabec

  DOI：10.1039/c4ta01933d

  日期：——

  The preparation of four different star-shaped donor (D)–π–acceptor (A) small molecules (N(Ph-1T-DCN-Me)3, N(Ph-2T-DCN-Me)3, N(Ph-2T-DCN-Hex)3 and N(Ph-3T-DCN-Hex)3) possessing various oligothiophene π-bridge lengths and their use in solution-processed bulk heterojunction small molecule solar cells is reported. Optical and electrochemical data show that increasing oligothiophene π-bridge length leads to a decrease of the optical band gap due to a parallel increase of the highest occupied molecular orbital (HOMO) level. Furthermore, subtle modifications of a molecular π-bridge length strongly affect the thermal behavior, solubility, crystallization, film morphology and charge carrier mobility, which in turn significantly change the device performance. Although the moderately increasing oligothiophene π-bridge length uplifts the HOMO level, it nevertheless induces an increase of the efficiency of the resulting solar cells due to a simultaneous improvement of the short circuit current (Jsc) and fill factor (FF). The study demonstrates that such an approach can represent an interesting tool for the effective modulation of the photovoltaic properties of the organic solar cells (OSCs) at a moderate cost.

  本文报道了四种不同星形供体（D）——受体（A）小分子（N（Ph-1T-DCN-Me）3、N（Ph-2T-DCN-Me）3、N（Ph-2T-DCN-Hex）3和N（Ph-3T-DCN-Hex）3）的制备，这些小分子具有不同的噻吩-桥长度，并用于溶液加工的体异质结小分子太阳能电池。光学和电化学数据表明，噻吩-桥长度的增加会导致光带隙的减小，这是由于最高被占分子轨道（HOMO）水平的平行增加。此外，分子-桥长度的细微变化会强烈影响热性能、溶解度、结晶、薄膜形态和电荷载流子迁移率，进而显著改变器件性能。虽然适度增加噻吩-桥长度会提升HOMO水平，但由于短路电流（Jsc）和填充因子（FF）同时提高，它仍然可以提高太阳能电池的效率。该研究表明，这种方法可以成为有效调节有机太阳能电池（OSC）的光电性能的有趣工具，且成本适中。
• Effects of bridging atom and π-bridge length on physical and photovoltaic properties of A–π-D–π-A oligomers for solution-processed organic solar cells
  作者：Yuriy N. Luponosov、Jie Min、Artem V. Bakirov、Petr V. Dmitryakov、Sergei N. Chvalun、Svetlana M. Peregudova、Tayebeh Ameri、Christoph J. Brabec、Sergei A. Ponomarenko

  DOI：10.1016/j.dyepig.2015.06.026

  日期：2015.11

  Synthesis of novel acceptor-donor-acceptor oligomers with electron-withdrawing alkyldicyanovinyl groups linked through an oligothiophene pi-bridge with either dithienosilole or cyclopentadithiophene electron donor units is described. Changing the bridgehead atom from carbon to silicon in the central donor unit leads to a significant change in optical, thermal and structural properties of the oligomers. In addition, elongation of the oligothiophene pi-bridge in the oligomers increases energies of HOMO and LUMO levels and leads to an unexpected hypsochromic shift of their absorption spectrum, because extension of the conjugation length cannot compensate a decrease of the intramolecular charge transfer between the dithienosilole and dicyanovinyl units. Although these minor changes in the chemical structures have a pronounced impact on the morphologies of their blends with PC70BM, the optimized solution-processed organic solar cells based on these small molecules demonstrate similar power conversion efficiencies. (C) 2015 Elsevier Ltd. All rights reserved.