4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-carbaldehyde | 1221821-38-0

• 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-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-carbaldehyde
• 英文别名: 4,4-Dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-carbaldehyde；7,7-dihexyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene-4-carbaldehyde
• CAS: 1221821-38-0
• 化学式: C₂₂H₃₀OS₂
• 分子量: 374.612
• InChiKey: BZZNTLQXZOSFIM-UHFFFAOYSA-N

物化性质

• 沸点：
  501.0±45.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-carbaldehyde 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 6-(5-(bis(4-(hexyloxy)phenyl)amino) thiophen-2-yl)-4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene-2-carbaldehyde
  参考文献：
  名称：

  Fine-tuning the Electronic Structure of Organic Dyes for Dye-Sensitized Solar Cells

  摘要：

  A series of metal-free organic dyes exploiting different combinations of (hetero)cyclic linkers (benzene, thiophene, and thiazole) and bridges (4H-cyclopenta[2,1-b:3,4-b']dithiophene (CPDT) and benzodithiophene (BDT)) as the central pi-spacers were synthesized and characterized. Among them, the sensitizer containing the thiophene and CPDT showed the most broad incident photon-to-current conversion efficiency spectra, resulting in a solar energy conversion efficiency (eta) of 6.6%.

  DOI：

  10.1021/ol301730c
• 作为产物：
  描述：

  4H-环戊并[2,1-B:3,4-B']二噻吩-4-酮 在 一水合肼 、 potassium iodide 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙二醇 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 生成 4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-carbaldehyde
  参考文献：
  名称：

  A Versatile Synthesis of Long-Wavelength-Excitable BODIPY Dyes from Readily Modifiable Cyclopenta[2,1-b:3,4-b′]dithiophenes

  摘要：

  Knoevenagel condensation of a simple methylated borondipyrromethene (Bodipy) with 4,4'-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophenes functionalized at one end by a triphenylamine residue and at the other by a carbaldehyde fragment leads to novel dye species. These bisvinylic derivatives exhibit pronounced absorption in the visible range extending above 850 nm. Addition of other Bodipy units by coupling to a central iodophenyl entity enables filling of the gaps in absorption of the pivotal starting material. Efficient cascade energy transfer between the Bodipys is facilitated by spectral overlap between the energy donor and the energy acceptor. All photons between 350 nm and 750 nm are channeled to the distyryl centers which emit at 864 nm.

  DOI：

  10.1055/s-0033-1341278

文献信息

• Oligomers of cyclopentadithiophene-vinylene in aromatic and quinoidal versions and redox species with intermediate forms
  作者：Paula Mayorga Burrezo、Rocío Domínguez、José L. Zafra、Ted M. Pappenfus、Pilar de la Cruz、Lorena Welte、Daron E. Janzen、Juan T. López Navarrete、Fernando Langa、Juan Casado

  DOI：10.1039/c7sc02756g

  日期：——

  A new series of π-conjugated oligomers based on the 4,4 dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene vinylene repeating unit has been prepared and characterized by X-ray, electrochemical, spectroscopic (UV-Vis absorption, emission and Raman) and density functional theory methods. The oligomers in their neutral, oxidized and reduced forms have been investigated. The neutral compounds show a longer

  基于 4,4 dihexyl-4 H -cyclopenta[2,1- b :3,4- b的新系列 π 共轭低聚物']二噻吩亚乙烯基重复单元的制备和表征采用X射线、电化学、光谱（UV-Vis吸收、发射和拉曼）和密度泛函理论方法。已经研究了中性、氧化和还原形式的低聚物。中性化合物显示出比低聚噻吩和低聚噻吩-亚乙烯基更长的平均共轭长度，并显示出非常丰富的氧化还原化学，具有聚阳离子态的稳定性，其中自由基阳离子和双阳离子是强 NIR 吸收剂，后者显示出单线态双自由基特性。已经描述和解释了自由基阳离子和双阳离子中芳香族醌结构片段序列之间有趣的互补性。4,4 dihexyl-4 H -cyclopenta[2,1-]的两个衍生物b :3,4- b ']二噻吩亚乙烯基单元，被电子供体、双（三芳基氨基）基团或受体双（二氰基-亚甲基）帽双取代，在二噻吩-亚乙烯基桥上形成醌式结构，也已合成和特点。三芳胺化合物
• Organic dyes and preparation method thereof and dye-sensitized solar cells
  申请人：Wang Peng

  公开号：US08586764B2

  公开（公告）日：2013-11-19

  An organic dye and preparation method thereof and dye-sensitized solar cells using this organic dye are provided. The structure of the organic dye molecule is donor-conjugated unit(s)-acceptor. The organic dye with broad spectrum response and high molar-absorption coefficient is obtained by modifying the structure by using various conjugated unit(s) in combination with donor and acceptor. The conditions of preparation of the organic dye are mild and the yield is high, and the organic dye can be used for highly effective dye-sensitized solar cells.

  本发明提供了一种有机染料及其制备方法，以及使用该有机染料的染料敏化太阳能电池。该有机染料分子的结构为给体-共轭单元-受体。通过使用不同的共轭单元与给体和受体相结合，修改结构得到具有宽谱响应和高摩尔吸光系数的有机染料。有机染料的制备条件温和，产率高，可用于高效的染料敏化太阳能电池。
• A donor–acceptor conjugated block copolymer of poly(arylenevinylene)s by ring-opening metathesis polymerization
  作者：Shu-Wei Chang、Masaki Horie

  DOI：10.1039/c5cc00498e

  日期：——

  A donor–acceptor conjugated block copolymer of poly(arylenevinylene)s has been synthesized by ring-opening metathesis polymerization.

  一种由环状开环重排聚合制备的供体-受体共轭嵌段聚合物，由聚芳烃乙烯基组成。
• Organic dyes with remarkably high absorptivity; all solid-state dye sensitized solar cell and role of fluorine substitution
  作者：Dong-Yi Chen、Yu-Yen Hsu、Hui-Chu Hsu、Bo-So Chen、Yi-Tsung Lee、Hungshin Fu、Min-Wen Chung、Shih-Hung Liu、Hsieh-Chih Chen、Yun Chi、Pi-Tai Chou

  DOI：10.1039/c0cc00808g

  日期：——

  A series of new organic D–π–A dyes, A1, A2-H and A2-F, possessing a remarkably high absorption extinction coefficient of ε > 5.0 × 104 M−1 cm−1 at peak wavelength were synthesized, among which, A2-F having a key fluorine substitution attains excellent all solid-state DSSC performance, with optimized parameters of η = 4.86%, JSC = 7.52 mA cm−2, VOC = 0.91 V, and FF = 0.71.

  合成了一系列新型有机 D–π–A 染料 A1、A2-H 和 A2-F，在峰值波长处具有极高的吸收消光系数 ε > 5.0 × 104 M−1 cm−1，其中，具有关键氟取代的 A2-F 获得了优异的全固态 DSSC 性能，优化参数为 η = 4.86%、JSC = 7.52 mA cm−2、VOC = 0.91 V 和 FF = 0.71。
• New cyclopentadithiophene (CDT) linked porphyrin donors with different end-capping acceptors for efficient small molecule organic solar cells
  作者：Susana Arrechea、Ana Aljarilla、Pilar de la Cruz、Manish Kumar Singh、Ganesh D. Sharma、Fernando Langa

  DOI：10.1039/c7tc00812k

  日期：——

  A–π–D–π–A molecules bearing a Zn-porphyrin core donor linked through cyclopenta[2,1-b:3,4-b′]dithiophene bridges to the electron-acceptor rhodanine (SA1) or dicyanovinylene (SA2) groups is described. The optical and electrochemical properties of these compounds are investigated. The horizontal conjugation of cyclopentadithiophene between the porphyrin core and the end-capping acceptor not only effectively

  带有锌卟啉核心供体的两个新的A–π–D–π–A分子的合成，这些分子通过环戊[2,1- b：3,4- b ']二噻吩桥连接至电子受体罗丹宁（SA1）描述了或二氰基亚乙烯基（SA2）基团。研究了这些化合物的光学和电化学性质。卟啉核心与封端受体之间的环戊二噻吩水平共轭不仅有效地提高了卟啉单元的Soret和Q谱带之间的光收集，而且还优化了通过线性π共轭骨架的分子堆积。化合物SA1和SA2与[6,6]-苯基-C 71一起用作给体-丁酸甲酯（PC 71 BM）作为有机本体异质结有机太阳能电池中的受体。在优化了活性层的工艺（溶剂添加剂和随后的溶剂蒸汽退火）之后，有机太阳能电池的总功率转换效率为6.71％和7.93％（低能量损失为0.55 eV）。溶剂添加剂的使用和随后的溶剂蒸气退火在活性层中提供了增强的纳米级形态和双连续互穿网络，这是有效激子离解成自由电荷载流子并随后向电极传输的必要条件。与基于铸态有源