2-(3-decylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 2-(3-decylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-decyl-thiophene
• 化学式: C₂₀H₃₅BO₂S
• 分子量: 350.374
• InChiKey: AOXGKQNATGEBBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-(3-decylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 、 溶剂黄146 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 25.0h， 生成 5,5'-bis(5-bromo-3-decylthiophen-2-yl)-2,2'-bithiazole
  参考文献：
  名称：

  Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells

  摘要：

  Two new small molecules, 5,5-bis(2-triphenylamino-3-decylthiophen-2-yl)-2,2-bithiazole (M1) and 2,5-bis(2-triphenylamino-3-decylthiophen-2-yl) thiazolo[5,4-d]thiazole (M2) based on an electron-donor triphenylamine unit and electron-acceptor thiophene-thiazolothiazole or thiophene-bithiazole units were synthesized by a palladium(0)-catalyzed Suzuki coupling reaction and examined as donor materials for application in organic solar cells. The small molecules had an absorption band in the range of 300-560 nm, with an optical band gap of 2.22 and 2.25 for M1 and M2, respectively. As determined by cyclic voltammetry, the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of M1 were -5.27 eV and -3.05 eV, respectively, which were 0.05 eV and 0.02 eV greater than that of M2. Photovoltaic properties of the small molecules were investigated by constructing bulk-heterojunction organic solar cell (OSC) devices using M1 and M2 as donors and fullerene derivatives, 6,6-phenyl-C61-butyric acid methyl ester (PC61BM) and 6,6-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptors with the device architecture ITO/PEDOT:PSS/M1 or M2:PCBM/LiF/Al. The effect of the small molecule/fullerene weight ratio, active layer thickness, and processing solvent were carefully investigated to improve the performance of the OSCs. Under AM 1.5 G 100 mW/cm(2) illumination, the optimized OSC device with M1 and PC71BM at a weight ratio of 1: 3 delivered a power conversion efficiency (PCE) of 1.30%, with a short circuit current of 4.63 mA/cm(2), an open circuit voltage of 0.97 V, and a fill factor of 0.29. In contrast, M2 produced a better performance under identical device conditions. A PCE as high as 2.39% was recorded, with a short circuit current of 6.49 mA/cm(2), an open circuit voltage of 0.94 V, and a fill factor of 0.39. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.11.016
• 作为产物：
  描述：

  频哪醇 、 3-癸基噻吩 在 aluminum (III) chloride 、 三氯化硼 、 N,N-二甲基对甲苯胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以93%的产率得到2-(3-decylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  [EN] PROCESS FOR THE BORYLATION OF ARENES AND HETEROARYLS
  [FR] PROCÉDÉ DE BORYLATION D'ARÈNES ET D'HÉTÉROARYLES

  摘要：

  这项发明涉及一种新型芳烃和杂环芳烃硼化的过程。本发明还提供了新型硼离子阳，它们作为芳烃或杂环芳烃环上亲电取代的亲电试剂，以及用于制备这些阳离子的方法学。

  公开号：

  WO2012025760A1

文献信息

• [EN] PROCESS FOR THE BORYLATION OF ARENES AND HETEROARYLS<br/>[FR] PROCÉDÉ DE BORYLATION D'ARÈNES ET D'HÉTÉROARYLES
  申请人：UNIV MANCHESTER

  公开号：WO2012025760A1

  公开（公告）日：2012-03-01

  This invention relates to a novel process for the borylation of arenes and heteroaryls. The present invention also provides novel borenium cations, which act as electrophiles for electrophilic substitution on the arene or heteroaryl ring, as well as to methodology for the preparation of these cations.

  这项发明涉及一种新型芳烃和杂环芳烃硼化的过程。本发明还提供了新型硼离子阳，它们作为芳烃或杂环芳烃环上亲电取代的亲电试剂，以及用于制备这些阳离子的方法学。
• Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells
  作者：Pranabesh Dutta、Wooseung Yang、Seung Hun Eom、Soo-Hyoung Lee

  DOI：10.1016/j.orgel.2011.11.016

  日期：2012.2

  Two new small molecules, 5,5-bis(2-triphenylamino-3-decylthiophen-2-yl)-2,2-bithiazole (M1) and 2,5-bis(2-triphenylamino-3-decylthiophen-2-yl) thiazolo[5,4-d]thiazole (M2) based on an electron-donor triphenylamine unit and electron-acceptor thiophene-thiazolothiazole or thiophene-bithiazole units were synthesized by a palladium(0)-catalyzed Suzuki coupling reaction and examined as donor materials for application in organic solar cells. The small molecules had an absorption band in the range of 300-560 nm, with an optical band gap of 2.22 and 2.25 for M1 and M2, respectively. As determined by cyclic voltammetry, the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of M1 were -5.27 eV and -3.05 eV, respectively, which were 0.05 eV and 0.02 eV greater than that of M2. Photovoltaic properties of the small molecules were investigated by constructing bulk-heterojunction organic solar cell (OSC) devices using M1 and M2 as donors and fullerene derivatives, 6,6-phenyl-C61-butyric acid methyl ester (PC61BM) and 6,6-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptors with the device architecture ITO/PEDOT:PSS/M1 or M2:PCBM/LiF/Al. The effect of the small molecule/fullerene weight ratio, active layer thickness, and processing solvent were carefully investigated to improve the performance of the OSCs. Under AM 1.5 G 100 mW/cm(2) illumination, the optimized OSC device with M1 and PC71BM at a weight ratio of 1: 3 delivered a power conversion efficiency (PCE) of 1.30%, with a short circuit current of 4.63 mA/cm(2), an open circuit voltage of 0.97 V, and a fill factor of 0.29. In contrast, M2 produced a better performance under identical device conditions. A PCE as high as 2.39% was recorded, with a short circuit current of 6.49 mA/cm(2), an open circuit voltage of 0.94 V, and a fill factor of 0.39. (C) 2011 Elsevier B. V. All rights reserved.