5,8-dibromo-2,3-bis(2-ethylhexyl)quinoxaline | 1203451-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,8-dibromo-2,3-bis(2-ethylhexyl)quinoxaline
• CAS: 1203451-22-2
• 化学式: C₂₄H₃₆Br₂N₂
• 分子量: 512.371
• InChiKey: VRLSGWKIRUKJMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.67
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  硼酸三甲酯 、 5,8-dibromo-2,3-bis(2-ethylhexyl)quinoxaline 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以68%的产率得到
  参考文献：
  名称：

  用于精确合成强供体/受体共轭聚合物的通用 Suzuki-Miyaura 催化剂转移聚合及其序列工程

  摘要：

  催化剂转移聚合因其活性特性而彻底改变了聚合物合成领域，但对于给定的催化剂体系，聚合物范围相当狭窄。在此，我们报告了一种高效的 Suzuki-Miyaura 催化剂转移聚合（SCTP），通过合理设计硼酸酯单体，涵盖从富电子（供体，D）到缺电子（受体，A）（杂）芳烃的广泛单体并使用市售的 Buchwald RuPhos 和 SPhos Pd G3 预催化剂。最初，我们通过引入新的硼酸盐，例如 4,4,8,8 优化了 3,4-丙烯二氧噻吩 (ProDOT)、苯并三唑 (BTz)、喹喔啉 (QX) 和 2,3-二苯基喹喔啉 (QXPh) 的受控聚合-四甲基-1,3,6,2-二氧杂硼烷及其N-苄基化衍生物，以调节单​​体的反应性和稳定性。结果，PProDOT、PBTz、PQX 和 PQXPh以优异的产率 (>85%)制备，具有受控的分子量和窄分散性 ( ± <1.29)。聚合物结构的详细研究使用1H

  DOI：

  10.1021/jacs.1c05080
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.83h， 生成 5,8-dibromo-2,3-bis(2-ethylhexyl)quinoxaline
  参考文献：
  名称：

  完全共轭的供体-受体-供体三嵌段共聚物的合成与表征

  摘要：

  建立一种合成方法以提供带有单个溴取代的端基的单官能远螯聚（3-辛基噻吩）（P3OT），其在制备明确的嵌段共聚物中具有潜在的用途。遥爪P3OT用催化剂转移缩聚5-溴-4-辛基-2-噻吩基由phenylnickel（II）引发剂引发的碘化物（CTCP）通过链生长工艺制备。淬灭反应的条件的优化允许在聚合物的末端安装α-溴官能团。我们通过将它定义为单官能聚合物Ph–P3OT–Br偶联到聚喹喔啉（PQ）带有硼酸酯末端基团，以提供新的一类供体-受体-供体（DA-D）三嵌段共聚物。三嵌段共聚物的形成通过凝胶渗透色谱法（GPC）和1 H NMR光谱法确认。使用紫外可见吸收和荧光光谱法研究了聚合物的光学性质。来自三嵌段共聚物的各个嵌段的荧光的有效猝灭与电子转移的发生是一致的。AFM图像说明了富电子的P3OT和贫电子的PQ块的纳米级相分离。

  DOI：

  10.1021/ma200084z

文献信息

• Synthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends
  作者：Chiu-Hsiang Chen、Chao-Hsiang Hsieh、Martin Dubosc、Yen-Ju Cheng、Chain-Shu Hsu

  DOI：10.1021/ma902206u

  日期：2010.1.26

  Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)(m)-(thiophene acceptor)(n), were rationally designed and successfully synthesized by the palladium-catalyzed Stille Coupling, The 4H-cyclopenta[2, 1-b:3,4-b']dithiophene (CPDT) unit serves as the donor for P1-P4, while file benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, respectively. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3.2-b:2',3'-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BR > QU presumably due to the quinoid form Population in the polymers, the optical band gaps call be well adjusted to be 1.2, 1.6, and 1.8 eV for P4, P1, and P2, respectively. It is found that file two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects oil the P1 and P5 as well as P2 and P6, respectively, leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based oil ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows it higher band gap with strong absorption in visible region, while PCPDTBT-has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P-1/PC71BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/PC7, BM (PCE = 1.4%) or P1/PC71 BM (PCE = 2.0%,,) Linder the identical conditions. Such an improvement is ascribed to file complementary absorption and compatible structure of P1 and PCPDTBT polymers.
• Synthesis and Characterization of New Self-Assembled Metallo-Polymers Containing Electron-Withdrawing and Electron-Donating Bis(terpyridine) Zinc(II) Moieties
  作者：Florian Schlütter、Andreas Wild、Andreas Winter、Martin D. Hager、Anja Baumgaertel、Christian Friebe、Ulrich S. Schubert

  DOI：10.1021/ma902110v

  日期：2010.3.23

  A series of rigid pi-conjugated bis(terpyridines) (M1-M7) bearing electron-acceptor spacer units in 4'-position was synthesized in moderate to high yields by Pd-0-catalyzed Sonogashira cross-coupling reactions. The compounds were fully characterized by NMR spectroscopy, MALDI-TOF mass spectrometry, elemental analysis and their photophysical properties were discussed in detail. These new bis(terpyridines) were applied for the self-assembly reaction with Zn-II ions to form metallo-homo polymers (P1-P7). Broadened NMR signals and UV-vis titration experiments confirmed the successful polymerization. The electro-optical properties of the materials were investigated in detail. Band gaps up to 2.08 eV and bright blue to orange photoluminescence with quantum yields of 18 to 66% were observed strongly depending on the nature of the pi-conjugated bis(terpyridine) system. In combination with electron-donor ditopic terpyridine ligands (MD1 and MD2), two Zn-II random copolymers (R1 and R2) were synthesized. These materials were investigated by UV-vis absorption and photoluminescence experiments in dilute solution and in the solid state, prepared by spin-coating from DMF Solutions. Thereby, random copolymer R2 featured an energy transfer from the donor to the acceptor part in dilute solution.