5,5''''''-diformyl-3,3',3'',3'''',3''''',3''''''-sexioctyl-2,5':2',5'':2'',2''':5''',2'''':5'''',2''''':5''''':2''''''-septithiophene | 1175560-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5''''''-diformyl-3,3',3'',3'''',3''''',3''''''-sexioctyl-2,5':2',5'':2'',2''':5''',2'''':5'''',2''''':5''''':2''''''-septithiophene
• 英文别名: DF7T；5-[5-[5-[5-[5-[5-(5-Formyl-3-octylthiophen-2-yl)-3-octylthiophen-2-yl]-3-octylthiophen-2-yl]thiophen-2-yl]-4-octylthiophen-2-yl]-4-octylthiophen-2-yl]-4-octylthiophene-2-carbaldehyde；5-[5-[5-[5-[5-[5-(5-formyl-3-octylthiophen-2-yl)-3-octylthiophen-2-yl]-3-octylthiophen-2-yl]thiophen-2-yl]-4-octylthiophen-2-yl]-4-octylthiophen-2-yl]-4-octylthiophene-2-carbaldehyde
• CAS: 1175560-77-6
• 化学式: C₇₈H₁₁₂O₂S₇
• 分子量: 1306.21
• InChiKey: XEYSDUNPNOVQRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  32.2
• 重原子数：
  87
• 可旋转键数：
  50
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  205
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  六氟乙酰丙酮 、 5,5''''''-diformyl-3,3',3'',3'''',3''''',3''''''-sexioctyl-2,5':2',5'':2'',2''':5''',2'''':5'''',2''''':5''''':2''''''-septithiophene 以 氯仿 、 溶剂黄146 为溶剂， 以93%的产率得到1,1,1,5,5,5-Hexafluoro-3-[[4-octyl-5-[4-octyl-5-[4-octyl-5-[5-[3-octyl-5-[3-octyl-5-[3-octyl-5-[4,4,4-trifluoro-3-oxo-2-(2,2,2-trifluoroacetyl)but-1-enyl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]methylidene]pentane-2,4-dione
  参考文献：
  名称：

  Photoelectric materials and preparation thereof

  摘要：

  受体型寡硫代噻吩化合物，制备这些化合物的方法，以及在光电材料中使用这些化合物的方法。

  公开号：

  US09184315B2
• 作为产物：
  描述：

  C₈₈H₁₃₂O₄S₇ 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5,5''''''-diformyl-3,3',3'',3'''',3''''',3''''''-sexioctyl-2,5':2',5'':2'',2''':5''',2'''':5'''',2''''':5''''':2''''''-septithiophene
  参考文献：
  名称：

  供体-受体低聚噻吩中吸电子基团和π共轭长度对其在非富勒烯有机太阳能电池中的性能和性能的影响

  摘要：

  开发用于高效非富勒烯 (NF) 有机太阳能电池 (OSC) 的小分子供体材料仍然是一项紧迫的研究任务。在这项工作中，报告了包含五个 (5T) 或七个 (7T) 噻吩单元的供体 - 受体分子的合成，这些噻吩单元以甲基二氰基乙烯基 (DCV) 或氰基乙酸乙酯 (CNA) 吸电子基团封端。综合研究和比较了它们与 IDIC 或 Y6 共混物作为受体材料的热稳定性、相行为、光学和电化学性能以及光伏性能。所有获得的供体分子都具有高热稳定性、高效的阳光吸收和优异的溶解性以及良好的结晶度。获得的结果使我们能够揭示低聚噻吩共轭长度和吸电子基团类型对 NF OSC 中 DA 低聚噻吩的性质和性能的影响。结果清楚地表明，基于具有 7T 或 CNA 片段的供体分子的装置明显优于基于 5T 或 DCV 组的装置。

  DOI：

  10.1016/j.dyepig.2021.109592

文献信息

• Impact of dye end groups on acceptor–donor–acceptor type molecules for solution-processed photovoltaic cells
  作者：Guangrui He、Zhi Li、Xiangjian Wan、Yongsheng Liu、Jiaoyan Zhou、Guankui Long、Mingtao Zhang、Yongsheng Chen

  DOI：10.1039/c2jm30194f

  日期：——

  Two new oligothiophene derivatives of the acceptor–donor–acceptor type, incorporating double rhodanine or 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione units as the terminal acceptor groups, D2R(8 + 2)7T and DTDMP7T, have been designed and synthesized for solution-processable small molecule BHJ solar cells. The impacts of these different end dye moieties on their optical, electrochemical properties, morphology, mobility and solar cell performance were studied. Both compounds exhibit broad and highly efficient solar absorption with low bandgaps of 1.70 and 1.62 eV for D2R(8 + 2)7T and DTDMP7T, respectively. The D2R(8 + 2)7T and DTDMP7T based BHJ solar cell devices achieved a PCE of 2.46% and 4.05%, respectively, under the illumination of AM.1.5, 100 mW cm−2.

  两种新型的受体-供体-受体型寡聚噻吩衍生物，采用双硫氮化合物或1,3-二甲基嘧啶-2,4,6(1H,3H,5H)-三酮单元作为末端受体基团，分别为D2R(8 + 2)7T和DTDMP7T，已被设计和合成用于可溶液处理的小分子BHJ太阳能电池。研究了这些不同末端染料基团对其光学、电化学性质、形态、迁移率和太阳能电池性能的影响。两种化合物均表现出宽频且高效的太阳能吸收，带隙分别低至1.70 eV和1.62 eV。基于D2R(8 + 2)7T和DTDMP7T的BHJ太阳能电池装置在AM 1.5、100 mW cm⁻²照射下，分别达到了2.46%和4.05%的光电转换效率(PCE)。
• Manipulation of the Open-Circuit Voltage of Organic Solar Cells by Desymmetrization of the Structure of Acceptor-Donor-Acceptor Molecules
  作者：Dora Demeter、Theodulf Rousseau、Philippe Leriche、Thomas Cauchy、Riccardo Po、Jean Roncali

  DOI：10.1002/adfm.201101508

  日期：2011.11.22

  The synthesis of acceptor–donor–acceptor (A–D–A) molecules based on a septithiophene chain with terminal electron acceptor groups is reported. Using a dicyanovinyl‐ (DCV) substituted molecule as reference, another symmetrical A–D–A donor containing thiobarbituric (TB) groups is synthesized and these two acceptor groups are combined to produce the unsymmetrical A–D–A′ compound. The electronic properties

  据报道，基于带有末端电子受体基团的噻吩并噻吩链的受体-供体-受体（AD）分子的合成。以双氰基乙烯基（DCV）取代的分子为参考，合成了另一个含有硫代巴比妥（TB）基团的对称A–D–A供体，并将这两个受体基团结合起来生成不对称的A–D–A'化合物。通过循环伏安法和UV-Vis吸收光谱分析供体的电子性质，并在双层平面异质结电池上表征其光伏性质，该平面异质结电池包括纺成的供体膜和真空沉积的C 60作为接受者。光学和电化学数据表明，用TB代替DCV会导致HOMO水平的小幅增加，而LUMO的大幅度下降，这会导致带隙减小。去对称化的化合物在溶液中的氧化电位最低，但在固态时的氧化起点最高，这导致所得太阳能电池的开路电压显着增加。
• Efficient small molecule bulk heterojunction solar cells with high fill factors via introduction of π-stacking moieties as end group
  作者：Guangrui He、Zhi Li、Xiangjian Wan、Jiaoyan Zhou、Guankui Long、Shuzhong Zhang、Mingtao Zhang、Yongsheng Chen

  DOI：10.1039/c2ta00496h

  日期：——

  Three new oligothiophene derivatives with an acceptor–donor–acceptor structure incorporating 1,3-indanedione or the derivative of 1,3-indanedione units as the terminal acceptor groups—DIN7T, DINCN7T and DDIN7T—have been designed and synthesized for solution-processable small molecule BHJ solar cells. The impacts of these different end dye moieties on the optical absorption, solubility, electrochemical properties, morphology, mobility and solar cell performance were studied. All three compounds exhibit broad and highly efficient solar absorption with a low bandgap. The DIN7T-based BHJ solar cell device achieved a PCE of 4.93% and a high fill factor of 0.72, under illumination of AM 1.5, 100 mW cm−2.

  我们设计并合成了三种新的低聚噻吩衍生物，它们具有以 1,3-茚二酮或 1,3-茚二酮单元的衍生物为末端受体基团的受体--DIN7T、DINCN7T 和 DDIN7T 结构，可用于溶液可处理小分子 BHJ 太阳能电池。研究了这些不同末端染料分子对光吸收、溶解性、电化学特性、形态、迁移率和太阳能电池性能的影响。所有这三种化合物都表现出广泛而高效的太阳能吸收和低带隙。基于 DIN7T 的 BHJ 太阳能电池装置在 AM 1.5、100 mW cmâ2 的照明条件下，PCE 达到 4.93%，填充因子高达 0.72。
• Oligothiophene based small molecules with a new end group for solution processed organic photovoltaics
  作者：Huijing Zhang、Xuan Yang、Nailiang Qiu、Wang Ni、Qian Zhang、Miaomiao Li、Bin Kan、Xiangjian Wan、Chenxi Li、Yongsheng Chen

  DOI：10.1016/j.orgel.2016.03.009

  日期：2016.6

  Two oligothiophene based small molecules (DINER5T and DINER7T) with a new end group INER were synthesized as the donors for organic solar cells, and their photovoltaic performance was studied and compared with the corresponding compounds (DRHD7T and DIN7T) with the same backbone structure but different end groups. Both of the new molecules exhibit broad and red shift absorption compared with DRHD7T

  两个低聚噻吩基于小分子（DINER5T和DINER7T）用新的端基INER合成为供体为有机太阳能电池，以及它们的光电性能进行了研究，并与相应的化合物（DRHD7T和DIN7T）具有相同的主链结构，但不同端组。与DRHD7T和DIN7T相比，这两种新分子均显示出宽泛的吸收和红移吸收，分别具有1.47 eV和1.34 eV的非常低的带隙。基于DINER5T：PC 71 BM和DINER7T：PC 71的设备通过使用CH 2 Cl 2的溶剂蒸汽退火（SVA）工艺，BM共混物膜的PCE分别为4.22％和4.02％。
• Impact of fluorinated end groups on the properties of acceptor–donor–acceptor type oligothiophenes for solution-processed photovoltaic cells
  作者：Guangrui He、Xiangjian Wan、Zhi Li、Qian Zhang、Guankui Long、Yongsheng Liu、Yanhui Hou、Mingtao Zhang、Yongsheng Chen

  DOI：10.1039/c3tc31709a

  日期：——

  Two new oligothiophene derivatives with the acceptor–donor–acceptor structure incorporating fluorinated alkyl cyanoacetate units as the terminal acceptor groups, DCAE7T-F1 and DCAO7T-F7, have been designed and synthesized for solution-processable BHJ solar cells. The impacts of these fluorinated end groups on the optical absorption, solubility, electrochemical properties, morphology, surface energy, film forming ability, mobility and solar cell performance were studied. We found that as the fluorinated alkyl length increased, the surface energy decreased and the lipophobicity increased. Due to its high lipophobic property and a problem with its wettability, DCAO7T-F7 was not able to produce a uniform film by spin coating. A power conversion efficiency (PCE) of 2.26% was achieved with an open-circuit voltage (Voc) of 0.83 V, short circuit current (Jsc) of 5.55 mA cm−2 and fill factor (FF) of 0.50 for DCAE7T-F1 based solar cells. The low Jsc suggests that controlling the film morphology and molecular assembly is essential for the performance of these fluorinated small molecules.

  我们设计并合成了两种新的低聚噻吩衍生物，即 DCAE7T-F1 和 DCAO7T-F7，它们具有受体-单体-受体结构，以氟化烷基氰基乙酸酯单元作为末端受体基团，可用于溶液可处理 BHJ 太阳能电池。研究了这些含氟末端基团对光吸收、溶解性、电化学性能、形貌、表面能、成膜能力、迁移率和太阳能电池性能的影响。我们发现，随着氟化烷基长度的增加，表面能降低，疏油性增加。由于 DCAO7T-F7 具有较高的疏脂性和润湿性，因此无法通过旋涂产生均匀的薄膜。基于 DCAE7T-F1 的太阳能电池的功率转换效率（PCE）为 2.26%，开路电压（Voc）为 0.83 V，短路电流（Jsc）为 5.55 mA cmâ2 ，填充因子（FF）为 0.50。低Jsc表明，控制薄膜形态和分子组装对这些含氟小分子的性能至关重要。