2-(3,4-dibutylthien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1313615-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(3,4-dibutylthien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1313615-33-6
• 化学式: C₁₈H₃₁BO₂S
• 分子量: 322.32
• InChiKey: KGHGILWJGYFGHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(3,4-dibutylthien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 mercury(II) acetate 、 cesium fluoride 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 116.5h， 生成 2,5-bis(3,4-dibutyl-2,2'-bithien-5-yl)selenophene
  参考文献：
  名称：

  Dicyanovinylene-Substituted Selenophene–Thiophene Co-oligomers for Small-Molecule Organic Solar Cells

  摘要：

  We report on the design, synthesis, and characterization of a series of terminal dicyanovinylene-substituted quinquechalcogenophenes as light-harvesting small-molecule donor materials for organic solar cells. The spectroscopic, electrochemical, and thermal properties of these pentamers were investigated. The replacement of thiophene unit(s) by selenophene(s) results in a bathochromic shift of the longest wavelength absorption band with concomitant increase of the molar extinction coefficient. Cyclic voltammetry measurements revealed fully reversible oxidation and irreversible reduction processes. The highest occupied and lowest unoccupied molecular orbital (HOMO/LUMO) energy levels were determined from electrochemical measurements and lie in the range of -5.6 and -3.8 eV. Vacuum-deposited bulk-heterojunction solar cells fabricated with the novel chalcogenophenes as donor and C-60 as acceptor displayed high open-circuit voltages of up to 1 V, short-circuit currents close to 8 mA.cm(-2), and power conversion efficiencies over 3%.

  DOI：

  10.1021/cm201392c
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 、 3,4-二丁基噻吩 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到2-(3,4-dibutylthien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Dicyanovinylene-Substituted Selenophene–Thiophene Co-oligomers for Small-Molecule Organic Solar Cells

  摘要：

  We report on the design, synthesis, and characterization of a series of terminal dicyanovinylene-substituted quinquechalcogenophenes as light-harvesting small-molecule donor materials for organic solar cells. The spectroscopic, electrochemical, and thermal properties of these pentamers were investigated. The replacement of thiophene unit(s) by selenophene(s) results in a bathochromic shift of the longest wavelength absorption band with concomitant increase of the molar extinction coefficient. Cyclic voltammetry measurements revealed fully reversible oxidation and irreversible reduction processes. The highest occupied and lowest unoccupied molecular orbital (HOMO/LUMO) energy levels were determined from electrochemical measurements and lie in the range of -5.6 and -3.8 eV. Vacuum-deposited bulk-heterojunction solar cells fabricated with the novel chalcogenophenes as donor and C-60 as acceptor displayed high open-circuit voltages of up to 1 V, short-circuit currents close to 8 mA.cm(-2), and power conversion efficiencies over 3%.

  DOI：

  10.1021/cm201392c

文献信息

• Synthesis and Physical Properties of Asymmetrical Quaterthiophene Derivatives as Organic Thin‐Film Transistor Materials
  作者：Baji Shaik、Young Ri Noh、Ho June Choi、Soon Byung Yoon、Myoung Hee Yun、Jin Young Kim、Sang‐Gyeong Lee

  DOI：10.1002/bkcs.10233

  日期：2015.4

  We report here, synthesis, physical, thermal, and optoelectronic properties of compounds containing anthracene, anthraquinone, and 11,11,12,12‐tetracyano‐9,10‐anthraquinodimethane units connected to quaterthiophene units. Three compounds, TQAO (6), TQAN (7), and TQAM (8) are synthesized by using Stille coupling, reduction, and Knoevenagel condensation reactions. These compounds were thermally stable and exhibited organic thin‐film transistor (OTFT) properties. Among them, TQAM (8)‐based OTFT has shown ambipolar mobility, both hole and electron mobility of 2.0 × 10⁻⁶ and 2.43 × 10⁻⁷ cm²/Vs, respectively. TQAO (6) and TQAN (7) has shown low electron mobility of 5.58 × 10⁻⁶ and 1.22 × 10⁻⁵ cm²/Vs, respectively.

  我们在此报告了含有蒽、蒽醌和 11,11,12,12-四氰基-9,10-蒽醌二甲烷单元与四联噻吩单元相连的化合物的合成、物理、热和光电特性。三种化合物 TQAO (6), TQAN (7) 和 TQAM (8) 是通过斯蒂尔偶联反应、还原反应和克诺文纳格尔缩合反应合成的。这些化合物具有热稳定性，并表现出有机薄膜晶体管（OTFT）的特性。其中 TQAM (8)-based OTFT 具有双极性迁移率，空穴和电子迁移率分别为 2.0 × 10-6 和 2.43 × 10-7 cm2/Vs。 TQAO (6) 和 TQAN (7) 的电子迁移率较低，分别为 5.58 × 10-6 和 1.22 × 10-5 cm2/Vs。