6-溴-4,4-二己基-4H-环戊并[1,2-B:5,4-B']二噻吩-2-甲醛 | 1221821-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 6-溴-4,4-二己基-4H-环戊并[1,2-B:5,4-B']二噻吩-2-甲醛
• 英文名称: 6-bromo-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-carbaldehyde
• 英文别名: 6-bromo-4,4-dihexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene-2-carbaldehyde；6-bromo-4,4-dihexyl-4H-cyclopenta[1,2-b；10-bromo-7,7-dihexyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene-4-carbaldehyde
• CAS: 1221821-39-1
• 化学式: C₂₂H₂₉BrOS₂
• 分子量: 453.508
• InChiKey: HCURECRAYBRAJM-UHFFFAOYSA-N

物化性质

• 沸点：
  534.1±50.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  26
• 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

安全信息

• 危险性防范说明：
  P264,P270,P301+P312,P330,P501
• 危险性描述：
  H302

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2-carbaldehyde	1221821-38-0	C22H30OS2	374.612
  4,4,-二己基-4H-环戊[2,1-B	4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene	153312-86-8	C21H30S2	346.601

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6-[4-(diphenylamino)phenyl]-4,4-dihexyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene-2-carbaldehyde	1315276-46-0	C40H43NOS2	617.92
  ——	(4,4'-dihexyl-cyclopenta[2,1-b:3,4-b']dithiophene-(2,2-dicyanovinyl)phenylazanediyl)dibenzoic acid	1332724-70-5	C45H43N3O4S2	753.986

反应信息

• 作为反应物：
  描述：

  6-溴-4,4-二己基-4H-环戊并[1,2-B:5,4-B']二噻吩-2-甲醛 在 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 38.0h， 生成 (4,4'-dihexyl-cyclopenta[2,1-b:3,4-b']dithiophene-(2,2-dicyanovinyl)phenylazanediyl)dibenzoic acid
  参考文献：
  名称：

  Arylamine-Based Dyes for p-Type Dye-Sensitized Solar Cells

  摘要：

  New arylamine-based sensitizers for p-type dye-sensitized solar cells (DSSCs) have been synthesized and used for p-type DSSCs. The best conversion efficiency reaches similar to 0.1%. Sensitizers with two anchoring carboxylic acids lead to higher open-circuit voltages, short-circuit currents, and energy conversion efficiencies.

  DOI：

  10.1021/ol202014x
• 作为产物：
  描述：

  4H-环戊并[2,1-B:3,4-B']二噻吩-4-酮 在 N-溴代丁二酰亚胺(NBS) 、 一水合肼 、 potassium iodide 、 potassium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 生成 6-溴-4,4-二己基-4H-环戊并[1,2-B:5,4-B']二噻吩-2-甲醛
  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

• New triphenylamine organic dyes containing dithieno[3,2-b:2′,3′-d]pyrrole (DTP) units for iodine-free dye-sensitized solar cells
  作者：Zhihui Wang、Mao Liang、Lina Wang、Yujie Hao、Chunbo Wang、Zhe Sun、Song Xue

  DOI：10.1039/c3cc42121j

  日期：——

  Three dithieno[3,2-b:2',3'-d]pyrrole (DTP) units with different hexyloxyphenyl (HOP) substituents have been developed for triphenylamine organic dyes (XS54-XS56). The introduction of the 4-HOP-DTP unit has resulted in a stronger light harvesting capacity, accounting for the observed photocurrent enhancement in the case of XS54, while the 2-HOP-DTP/2,4-HOP-DTP units induce a strikingly large photovoltage

  对于三苯胺有机染料（XS54-XS56），已开发出具有不同己基氧基苯基（HOP）取代基的三个二噻吩并[3,2-b：2'，3'-d]吡咯（DTP）单元。4-HOP-DTP单元的引入导致了更强的光收集能力，这是在XS54情况下观察到的光电流增强的原因，而2-HOP-DTP / 2,4-HOP-DTP单元则引人注目由于XS55和XS56具有更高的位阻，因此可以大大提高光电压。
• Molecular Engineering of Organic Dyes for Improved Recombination Lifetime in Solid-State Dye-Sensitized Solar Cells
  作者：William H. Nguyen、Colin D. Bailie、Julian Burschka、Thomas Moehl、Michael Grätzel、Michael D. McGehee、Alan Sellinger

  DOI：10.1021/cm3036357

  日期：2013.5.14

  solar cells is a short electron diffusion length, which is due to fast recombination between electrons in the TiO2 electron-transporting layer and holes in the 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (Spiro-OMeTAD) hole-transporting layer. In this report, the sensitizing dye that separates the TiO2 from the Spiro-OMeTAD was engineered to slow recombination and increase device

  固态染料敏化太阳能电池的主要限制是电子扩散长度短，这是由于TiO 2电子传输层中的电子与2,2'，7,7'-四原子中的空穴之间的快速复合（N，N-二-对甲氧基苯胺）-9,9'-螺双芴（Spiro-OMeTAD）空穴传输层。在本报告中，分离TiO 2的增感染料Spiro-OMeTAD的产品经过精心设计，可减慢重组速度并提高设备性能。通过合成和表征三种新型有机D-π-A增感染料（WN1，WN3和WN3.1），发现烷基链在增感染料上的数量和位置在抑制重组中起着重要作用。在使用Spiro-OMeTAD作为空穴传输材料的固态设备中，这些染料实现了以下效率：WN1达到4.9％，WN3达到5.9％，WN3.1达到6.3％，而Y123则达到了6.6％。参考染料。在这项研究中研究的染料中，使用瞬态光电压和光电流测量，WN3.1被证明在抑制固态染料敏化太阳能电池中的重组方面最有效。
• A hybrid electron donor comprising cyclopentadithiophene and dithiafulvenyl for dye-sensitized solar cells
  作者：Gleb Sorohhov、Chenyi Yi、Michael Grätzel、Silvio Decurtins、Shi-Xia Liu

  DOI：10.3762/bjoc.11.118

  日期：——

  Two new photosensitizers featured with a cyanoacrylic acid electron acceptor (A) and a hybrid electron donor (D) of cyclopentadithiophene and dithiafulvenyl, either directly linked or separated by a phenyl ring, were synthesized and characterized. Both of them undergo two reversible oxidations and strongly absorb in the visible spectral region due to a photo-induced intramolecular charge-transfer (ICT) transition. To a great extent, the electronic interaction between the D and A units is affected by the presence of a phenyl spacer. Without a phenyl ring, the D unit appears more difficult to oxidize due to a strong electron-withdrawing effect of the A moiety. In sharp contrast, the insertion of the phenyl ring between the D and A units leads to a broken π-conjugation and therefore, the oxidation potentials remain almost unchanged compared to those of an analogue without the A group, suggesting that the electronic coupling between D and A units is relatively weak. As a consequence, the lowest-energy absorption band shows a slight hypsochromic shift upon the addition of the phenyl spacer, indicative of an increased HOMO–LUMO gap. In turn, the direct linkage of D and A units leads to an effective π-conjugation, thus substantially lowering the HOMO–LUMO gap. Moreover, the application in dye-sensitized solar cells was investigated, showing that the power conversion efficiency increases by the insertion of the phenyl unit.

  合成并表征了两种新的光敏剂，其特点是具有氰基丙烯酸电子受体（A）和由环戊二硫苯和二硫富烯基组成的杂化电子给体（D），可以直接连接或通过苯环分离。它们都经历了两次可逆氧化反应，并且由于光诱导分子内电荷转移（ICT）跃迁，在可见光谱区强烈吸收。D和A单元之间的电子相互作用在很大程度上受到苯基间距的影响。没有苯环时，由于A基团的强电子吸引作用，D单元更难氧化。相比之下，将苯环插入D和A单元之间会破坏π-共轭，因此氧化电位与没有A基团的类似物相比几乎不变，表明D和A单元之间的电子耦合相对较弱。因此，最低能量吸收带在加入苯基间距后显示出轻微的向蓝移，表明HOMO-LUMO间隙增加。相反，D和A单元的直接连接导致有效的π-共轭，从而大大降低了HOMO-LUMO间隙。此外，还研究了其在染料敏化太阳能电池中的应用，插入苯基单元可以提高其功率转换效率。
• 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。