4-正辛基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩 | 405165-12-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 4-正辛基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩
• 中文别名: 4,4,5,5-四甲基-2-(4-正辛基-2-噻吩基)-1,3,2-二氧环戊硼烷；4-n-辛基-2-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)噻吩；4-N-辛基-2-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)噻吩
• 英文名称: 4,4,5,5-tetramethyl-2-(4-octylthiophen-2-yl)-1,3,2-dioxaborolane
• CAS: 405165-12-0
• 化学式: C₁₈H₃₁BO₂S
• 分子量: 322.32
• InChiKey: RKYWQDDPNVTJJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-正辛基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Intertwined Lamello-Columnar Coassemblies in Liquid-Crystalline Side-Chain Π-Conjugated Polymers: Toward a New Class of Nanostructured Supramolecular Organic Semiconductors

  摘要：

  A set of liquid-crystalline polymeric systems, associating at once the regioregular polythiophene backbone and pending mesogenic triphenylenes, is reported. Two series, namely regular homopolymers and alternating copolymers, were prepared by adapting a Grignard metathesis-based methodology, allowing some of the relevant structural parameters to be sequentially and independently modified. The thermal and self-organization behaviors of these uncommon macromolecular systems were investigated by polarized-light optical microscopy, differential scanning calorimetry and temperature-dependent small-angle X-ray scattering. Most polymers self-organize into mesophases possessing intertwined lamello-columnar morphologies, resulting from the simultaneous coexistence of lamellar and columnar sublattices. The successful preparation of oriented thin films of several of these polymeric homologues allowed further investigations by atomic force microscopy, transmission electron microscopy, electron diffraction, and grazing-incidence SAXS, which provided a deeper insight of the intricate supramolecular organizational modes, including the complete elucidation of the structure of the lamello-columnar mesophases. This simple and versatile strategy provides a route to elaborate polymeric materials incorporating two intercalated separate pathways toward charge carrier transport, of paramount importance for future electronic and optoelectronic applications.

  DOI：

  10.1021/ma4020356
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 、 3-辛基噻吩 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4-正辛基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩
  参考文献：
  名称：

  Enhanced device performance of organic solar cells via reduction of the crystallinity in the donor polymer

  摘要：

  一种新的π共轭聚合物，聚(2,5-二辛氧基苯乙烯-交替-3,3-二辛基四硫烯)（PPVQT-C8），由交替的p-二烯基苯和3,3-二烷基四硫烯单元组成，旨在用于有机太阳能电池设备。通过在成对的四硫烯单元之间引入p-二烯基苯单元，聚（四硫烯）(PQT)的结晶度得到降低。这种改性产生了PPVQT-C8:PCBM光活性层的良好混合纳米级形态，相比于基于高结晶度PQT的设备，提高了光电转化效率。基于PPVQT-C8:PC60BM以1:3比例混合的体异质结太阳能电池表现出最佳光伏性能，短路电流密度(Jsc)为6.7 mA cm−2，开路电压(Voc)为0.67 V，填充因子(FF)为0.62，光电转化效率(PCE)为2.8%，在光强为100 mW cm−2的AM 1.5照射下。此外，载流子迁移率和形态研究表明，在1:3混合比例中，可以实现由PPVQT-C8:PCBM构成的优化互穿网络。

  DOI：

  10.1039/c0jm00664e

文献信息

• Side chain engineering and conjugation enhancement of benzodithiophene and phenanthrenequnioxaline based conjugated polymers for photovoltaic devices
  作者：Ying Sun、Chao Zhang、Bin Dai、Baoping Lin、Hong Yang、Xueqin Zhang、Lingxiang Guo、Yurong Liu

  DOI：10.1002/pola.27643

  日期：2015.8.15

  spacer in polymer P2 greatly suppressed the interannular twisting to extend the effective conjugation length and consequently gave rise to improved absorption property and device performance. In addition, utilizing the alkylthienyl side chains to replace the alkyl side chains at BDT unit in polymer P3 further enhanced the photovoltaic performance due to the increased conjugation length. For polymer P4, translating

  设计并合成了一系列结合了苯并二噻吩（BDT）作为供体单元和邻菲咯啉二恶唑啉作为具有不同侧链的受体单元的供体-受体共轭聚合物。对于在主链中具有BDT单元和烷氧基链取代的邻菲咯啉衍生物的聚合物P1而言，严重的位阻导致分子量非常低。聚合物P2中噻吩环间隔基的实施极大地抑制了环间扭曲，从而延长了有效的共轭长度，因此提高了吸收性能和器件性能。另外，由于共轭长度的增加，利用烷基噻吩侧链取代聚合物P3中BDT单元的烷基侧链进一步提高了光伏性能。对于聚合物P4，将菲咯啉镍恶啉环上的烷氧基侧链翻译成噻吩连接基团上的烷基侧链可增强分子平面性并增强π-π堆积。因此，获得了聚合物P4的改善的吸收性质和增加的空穴迁移率。我们的结果表明，侧链工程不仅可以影响聚合物的溶解度，而且可以确定聚合物主链的平面度，从而确定光伏性能。©2015 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学
• Design and synthesis of N-substituted perylene diimide based low band gap polymers for organic solar cell applications
  作者：Savita Meena、Tauheed Mohammad、Viresh Dutta、Josemon Jacob

  DOI：10.1039/c8ra05232h

  日期：——

  2-dioxaborolan-2-yl)-9H-carbazole M3, respectively. The copolymer P3 was synthesized by direct arylation polymerization of M1 with 4,7-bis(4-octylthiophen-2-yl)benzo[c]-1,2,5-thiadiazole M4. All the copolymers showed thermal stability greater than 380 °C as evidenced from thermogravimetric analysis. The copolymers exhibited a narrow optical band gap (1.80–2.08 eV) with their UV-visible absorption spectra

  在这项研究中，我们报告了一系列新型共聚物的合成和器件研究，这些共聚物含有 N-取代的苝二酰亚胺和二辛基芴单元作为主要骨架的一部分。通过苝-3,4,9,10-四羧酸二酐与2-氨基-7-溴-9,9-二辛基芴的反应，使用一种避免非选择性溴化的简便合成方法来合成单体M1 。共聚物P1和P2是通过M1与 2,2'-(9,9-dioctyl-9 H -fluoren-2,7-diyl)bis(4,4,5,5-tetramethyl-1)的 Suzuki 缩聚反应合成的， 3,2-dioxaborolane) M2和 9-(heptadecan-9-yl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9 H -咔唑M3，分别。共聚物P3通过M1与4,7-双(4-辛基噻吩-2-基)苯并[ c ]-1,2,5-噻二唑M4的直接芳基化聚合合成。热重分析表明，所有共聚物的热稳定性均大于
• 5,6-Difluorobenzothiadiazole and silafluorene based conjugated polymers for organic photovoltaic cells
  作者：Guangwu Li、Chong Kang、Xue Gong、Jicheng Zhang、Weiwei Li、Cuihong Li、Huanli Dong、Wenping Hu、Zhishan Bo

  DOI：10.1039/c4tc00340c

  日期：——

  Three novel 5,6-difluorobenzothiadiazole and silafluorene based conjugated polymers have been synthesized and used as donor materials for polymer solar cells.

  三种基于新型5,6-二氟苯并噻二唑和硅芴的共轭聚合物已经合成，并用作聚合物太阳能电池的给体材料。
• [EN] ORGANIC DYE FOR A DYE SENSITIZED SOLAR CELL<br/>[FR] COLORANT ORGANIQUE POUR CELLULE PHOTOVOLTAÏQUE SENSIBILISÉE PAR COLORANT
  申请人：ENI SPA

  公开号：WO2017199151A1

  公开（公告）日：2017-11-23

  An organic dye for a Dye Sensitized Solar Cell (DSSC) which comprises at least one electron acceptor unit and at least one ττ-conjugated unit. Said organic dye is particularly useful in a dye sensitized photoelectric conversion element which, in turn, may be used in a dye sensitized solar cell (DSSC).

  一种有机染料，用于染料敏化太阳能电池（DSSC），其包括至少一个电子受体单元和至少一个ττ-共轭单元。该有机染料在染料敏化光电转换元件中特别有用，该元件反过来可用于染料敏化太阳能电池（DSSC）。
• New Chiral Thiophene−Salen Chromium Complexes for the Asymmetric Henry Reaction
  作者：Anaïs Zulauf、Mohamed Mellah、Emmanuelle Schulz

  DOI：10.1021/jo802769y

  日期：2009.3.6

  Chiral thiophene-salen chromium complexes were investigated in their monomeric form as soluble catalysts in the enantioselective Henry reaction of several aldehydes. The anodic polymerization of one complex led to an insoluble powder that was successfully used as a heterogeneous catalyst for the transformation of 2-methoxybenzaldehyde with enantiomeric excesses up to 77%. The polymerized catalyst was recovered and also recycled in an original multisubstrate procedure.