4,4'-dioctyl-5,5'-bis(trimethylsilnae)thieno[3,2-b:2',3'-d]silole | 1203451-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4,4'-dioctyl-5,5'-bis(trimethylsilnae)thieno[3,2-b:2',3'-d]silole
• 英文别名: 4,4'-dioctyl-2,6-bis(trimethylsilyl)dithieo[3,2-b:2',3'-d]silole；4,4-dioctyl-2,6-bis(trimethylsilyl)-4H-dithieno[3,2-b:2',3'-d]silole；(7,7-Dioctyl-10-trimethylsilyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl)-trimethylsilane；(7,7-dioctyl-10-trimethylsilyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl)-trimethylsilane
• CAS: 1203451-18-6
• 化学式: C₃₀H₅₄S₂Si₃
• 分子量: 563.147
• InChiKey: YOTZZCKDPJGOJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.16
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-dioctyl-5,5'-bis(trimethylsilnae)thieno[3,2-b:2',3'-d]silole 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以0.83 g的产率得到3,3'-二辛基硅基-2,2'-联噻吩
  参考文献：
  名称：

  具有双噻吩并硅氧硅核的A-π-D-π-A噻吩基材料的光电性能：实验和理论研究。

  摘要：

  合成了两个具有中央二噻吩甲硅油烯核心和双氰基乙烯基（DCV）端基的A-π-D-π-A噻吩基小分子。这些化合物的区别仅在于噻吩β位置分别存在烷基和烷基硫烷基链。计算数据以及光谱和电化学结果（通过吸收，稳态/时间分辨发射技术和循环伏安法获得）表明，这两种分子均具有低的电子和光学带隙，宽的吸收光谱以及良好的稳定性处于p和n掺杂状态，使其适合于光电应用。在这两种化合物中，HOMO-LUMO跃迁都涉及分子内电荷从电子给体二硫杂硅醇单元转移到两个末端电子受体DCV基团的过程。对于两个分子均观察到明显的正发射溶剂变色现象，并基于在S1激发态下的对称性断裂来解释。还将这两种合成的化合物与其较短的前体和类似的寡噻吩进行了比较，以了解构件的性质如何影响最终材料的特性。此外，有可能更好地理解硫原子在调节所研究的小分子的光学性质中的作用。还将这两种合成的化合物与其较短的前体和类似的寡噻吩进行了比较，以了解构件的性

  DOI：

  10.1002/cplu.201900092
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 4,4'-dioctyl-5,5'-bis(trimethylsilnae)thieno[3,2-b:2',3'-d]silole
  参考文献：
  名称：

  Synthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends

  摘要：

  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.

  DOI：

  10.1021/ma902206u

文献信息

• 유기 반도체 화합물 및 제조방법과 이를 포함하는 유기전자소자
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR101495152B1

  公开（公告）日：2015-02-26

  본 발명은 유기 반도체 화합물, 이의 제조방법 및 이를 포함하는 유기전자소자에 관한 것으로, 보다 상세하게는 퀴녹살린을 포함하는 유기 반도체 화합물, 이의 제조방법 및 이를 포함하는 유기전자소자에 관한 것이다. 또한 황(S)을 포함하고 있는 티오펜 유도체를 합성하여 퀴녹살린계 화합물과 공중합하여 낮은 밴드갭을 나타내므로, 이를 포함하는 유기전자소자는 본 발명의 유기 반도체 화합물과 광활성층인 풀러렌 유도체와의 획기적인 조합으로 높은 효율을 가진다. 또한 본 발명의 유기 반도체 화합물은 높은 열적 안정성과 높은 용해도로 인해 이를 포함하는 유기전자소자는 우수한 전기특성을 가져 유기전자 소자 특히, 유기 태양전지 또는 유기박막트랜지스터의 n-type 재료로서 매우 유용하게 사용될 수 있다.

  本发明涉及有机半导体化合物、其制备方法以及包含该有机半导体化合物的有机电子器件，更详细地说，涉及包含奎诺萨林的有机半导体化合物、其制备方法以及包含该化合物的有机电子器件。此外，通过合成含硫基团的噻吩衍生物与奎诺萨林类化合物进行共聚，显示出较低的带隙，因此，包含该化合物的有机电子器件通过与本发明的有机半导体化合物和富勒烯衍生物作为光活性层的显著组合具有高效率。此外，由于本发明的有机半导体化合物具有高热稳定性和高溶解度，包含该化合物的有机电子器件具有优异的电学特性，因此，该有机电子器件特别适用于有机太阳能电池或有机薄膜晶体管的n-型材料。