5,5″″-diformaldehyde-3,3′,3,3″″-tetraoctyl-2,5′:2′,5″:2″,2′″:5′″,2″″-pentathiophene | 1175560-76-5

• 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″″-diformaldehyde-3,3′,3,3″″-tetraoctyl-2,5′:2′,5″:2″,2′″:5′″,2″″-pentathiophene
• 英文别名: 3,3''',3'",4'-tetraoctyl-[2,2':5',2":5",2"',5'",2"''-pentathienophene]-5,5''''-dicarbaldehyde；DF5T；5,5''''-diformyl-3,3''',3'''',4'-tetraoctyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene；5-[5-[5-[5-(5-Formyl-3-octylthiophen-2-yl)-3-octylthiophen-2-yl]thiophen-2-yl]-4-octylthiophen-2-yl]-4-octylthiophene-2-carbaldehyde；5-[5-[5-[5-(5-formyl-3-octylthiophen-2-yl)-3-octylthiophen-2-yl]thiophen-2-yl]-4-octylthiophen-2-yl]-4-octylthiophene-2-carbaldehyde
• CAS: 1175560-76-5
• 化学式: C₅₄H₇₆O₂S₅
• 分子量: 917.526
• InChiKey: SNBJTFGNYSWERT-UHFFFAOYSA-N

物化性质

• 沸点：
  898.0±65.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  21.3
• 重原子数：
  61
• 可旋转键数：
  34
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,5″″-diformaldehyde-3,3′,3,3″″-tetraoctyl-2,5′:2′,5″:2″,2′″:5′″,2″″-pentathiophene 、 6-(4-氧代-2-三氧噻唑烷-3-基)-己酸 在 ammonium acetate 、 溶剂黄146 作用下， 以70%的产率得到
  参考文献：
  名称：

  Chirality inversion in hydrogen-bonded rhodanine–oligothiophene derivatives by solvent and temperature

  摘要：

  使用外部刺激，如溶剂和温度，可以通过单个手性氢键π共轭系统的对映体实现超分子手性的反转。

  DOI：

  10.1039/d1cc05945a
• 作为产物：
  描述：

  2-溴-3-辛基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 magnesium 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醚 、 氯仿 、 1,2-二氯乙烷 、 1,2-二溴乙烷 为溶剂， 反应 2.0h， 生成 5,5″″-diformaldehyde-3,3′,3,3″″-tetraoctyl-2,5′:2′,5″:2″,2′″:5′″,2″″-pentathiophene
  参考文献：
  名称：

  Chirality inversion in hydrogen-bonded rhodanine–oligothiophene derivatives by solvent and temperature

  摘要：

  使用外部刺激，如溶剂和温度，可以通过单个手性氢键π共轭系统的对映体实现超分子手性的反转。

  DOI：

  10.1039/d1cc05945a

文献信息

• 有机光电材料制备
  申请人：南开大学

  公开号：CN104774200B

  公开（公告）日：2018-01-23

  公开了式(I)所示的有机光电材料及其制备方法和用途，其中，R1至R11、n、m、x、y和z的定义如本申请所定义。
• 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％。
• Effects of electron-withdrawing group and π-conjugation length in donor-acceptor oligothiophenes on their properties and performance in non-fullerene organic solar cells
  作者：Nadezhda K. Kalinichenko、Dmitry O. Balakirev、Petr S. Savchenko、Artur L. Mannanov、Svetlana M. Peregudova、Dmitry Yu. Paraschuk、Sergey A. Ponomarenko、Yuriy N. Luponosov

  DOI：10.1016/j.dyepig.2021.109592

  日期：2021.10

  and electrochemical properties as well as photovoltaic performance in blends with IDIC or Y6 as acceptor materials were comprehensively investigated and compared. All of the obtained donor molecules are characterized by high thermal stability, efficient sunlight absorption and excellent solubility in combination with a good crystallinity. The results obtained allowed us to reveal the impact of the oligothiophene

  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。
• A Series of Simple Oligomer-like Small Molecules Based on Oligothiophenes for Solution-Processed Solar Cells with High Efficiency
  作者：Bin Kan、Miaomiao Li、Qian Zhang、Feng Liu、Xiangjian Wan、Yunchuang Wang、Wang Ni、Guankui Long、Xuan Yang、Huanran Feng、Yi Zuo、Mingtao Zhang、Fei Huang、Yong Cao、Thomas P. Russell、Yongsheng Chen

  DOI：10.1021/jacs.5b00305

  日期：2015.3.25

  A series of acceptor-donor-acceptor simple oligomer-like small molecules based on oligothiophenes, namely, DRCN4T-DRCN9T, were designed and synthesized. Their optical, electrical, and thermal properties and photovoltaic performances were systematically investigated. Except for DRCN4T, excellent performances were obtained for DRCN5T-DRCN9T. The devices based on DRCN5T, DRCN7T, and DRCN9T with axisyrnmetric chemical structures exhibit much higher short-circuit current densities than those based on DRCN6T and DRCN8T with centrosymmetric chemical structures, which is attributed to their well-developed fibrillar network with a feature size less than 20 nm. The devices based on DRCN5T/PC71BM showed a notable certified power conversion efficiency (PCE) of 10.10% under AM 1.5G irradiation (100 mW cm(-2)) using a simple solution spin-coating fabrication process. This is the highest PCE for single-junction small-molecule-based organic photovoltaics (OPVs) reported to date. DRCN5T is a rather simpler molecule compared with all of the other high-performance molecules in OPVs to date, and this might highlight its advantage in the future possible commercialization of OPVs. These results demonstrate that a fine and balanced modification/design of chemical structure can make significant performance differences and that the performance of solution-processed small-molecule-based solar cells can be comparable to or even surpass that of their polymer counterparts.
• Synthesis and properties of acceptor–donor–acceptor molecules based on oligothiophenes with tunable and low band gap
  作者：Yongsheng Liu、Jiaoyan Zhou、Xiangjian Wan、Yongsheng Chen

  DOI：10.1016/j.tet.2009.04.089

  日期：2009.7

  A series of acceptor-donor-acceptor molecules (DCN3T, DCN5T and DCN7T) based on oligothiophenes with low band gap are synthesized. The UV-vis absorption spectra of solution show that the introduction of electron-accepting groups results in a shift of the absorption onset towards longer wavelengths. Moreover, the optical spectra of their films show a large bathochromic shift and broadening of the bands with respect to the spectra in solution. The optical band gaps of film of these A-D-A molecules are 1.90, 1.74 and 1.68 eV, respectively. Cyclic voltammetry shows that all these compounds present a reversible first oxidation process whose potential decreases with the lengthening of oligothiophene cores. Electrochemical band gaps are 2.14, 1.88 and 1.71 eV, respectively. (C) 2009 Elsevier Ltd. All rights reserved.