环戊联噻吩 | 389-58-2

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 环戊联噻吩
• 中文别名: 4H-环戊[2,1-b:3,4-b']二噻吩；4H-环戊并[2,1-b:3,4-b']二噻吩；二噻吩并环戊二烯；4H-环戊并[2,1-B:3,4-B]二噻吩；四氢-环戊[2,1-B:3,4-B']二噻吩；4H-环戊[1,2-b:5,4-b']二噻吩；K0130
• 英文名称: 4H-cyclopenta[2,1-b;3,4-b']dithiophene
• 英文别名: 4H-cyclopenta-[2,1-b;3,4-b’]-dithiophene；CPDT；4H-cyclopenta[1,2-b:5,4-b']dithiophene；cyclopenta[2,1-b:3,4-b']dithiophene；dithienocyclopentadiene；4H-cyclopenta[2,1-b:3,4-b′]dithiophene；cyclopenta[2,1-b ;3,4-b′]dithiophene；4H-cyclopenta[2,1-b:3,4-b']bithiophene；3,4-dithia-7H-cyclopenta[a]pentalene；cyclopentadithiophene；4H-Cyclopenta[2,1-b:3,4-b']dithiophene；3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 389-58-2
• 化学式: C₉H₆S₂
• 分子量: 178.279
• InChiKey: UITASDKJJNYORO-UHFFFAOYSA-N

物化性质

• 熔点：
  71.0 to 75.0 °C
• 沸点：
  307.8±22.0 °C(Predicted)
• 密度：
  1.400
• 溶解度：
  溶于甲苯
• 最大波长(λmax)：
  305nm(EtOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C

SDS

4H-Cyclopenta[2,1-b:3,4-b']dithiophene
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4H-Cyclopenta[2,1-b:3,4-b']dithiophene
5.3

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4H-Cyclopenta[2,1-b:3,4-b']dithiophene
Percent: >97.0%(GC)
CAS Number: 389-58-2
Synonyms: 4H-Cyclopenta[1,2-b:5,4-b']dithiophene
Chemical Formula: C9H6S2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
4H-Cyclopenta[2,1-b:3,4-b']dithiophene

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a refrigerator.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive, Air-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Very pale yellow - Pale yellow green
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:73°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents]
4H-Cyclopenta[2,1-b:3,4-b']dithiophene

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Soluble: Toluene

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Sulfur oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
4H-Cyclopenta[2,1-b:3,4-b']dithiophene

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

环戊联噻吩在给体-受体共聚物的合成中是有用的。 环戊联噻吩还可用于合成供体-受体共聚物。

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
  4H-环戊并[2,1-B:3,4-B']二噻吩-4-酮	4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one	25796-77-4	C9H4OS2	192.262
  ——	4H-4-Carboxycyclopenta<2,1-b:3,4-b'>dithiophene	78196-93-7	C10H6O2S2	222.288

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2,6-二溴-4H-环戊并[1,2-b:5,4-b]二噻吩	2,6-dibromo-4H-cyclopenta-[2,1-b:3,4-b’]dithiophene	258527-25-2	C9H4Br2S2	336.071
  ——	4,4-dimethyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene	153312-83-5	C11H10S2	206.332
  ——	4,4-diethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene	1253119-62-8	C13H14S2	234.386
  ——	4H-4-Carboxycyclopenta<2,1-b:3,4-b'>dithiophene	78196-93-7	C10H6O2S2	222.288
  ——	4,4-dibutylcyclopenta[2,1-b;3,4-b']bithiophene	——	C17H22S2	290.494
  ——	4,4-didodecyl-4H-cyclopenta[2,1-b:3,4-b’]dithiophene	1201921-87-0	C33H54S2	514.924
  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
  4,4-二辛基-环戊并[2,1-b:3,4-b]二噻吩	4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene	153312-87-9	C25H38S2	402.709
  ——	4,4-dihexadecyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene	153312-88-0	C41H70S2	627.139
  ——	4,4'-bis-(8-bromoctyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene	——	C25H36Br2S2	560.501

反应信息

• 作为反应物：
  描述：

  环戊联噻吩 在 正丁基锂 作用下， 生成 6-(3,11-Dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-7-yl)hexanenitrile
  参考文献：
  名称：

  羧基封端的二噻吩和三噻吩分子在 ITO 电极上的吸附及其与聚合物层的电化学偶联。分子几何的影响

  摘要：

  羧戊基和羧己基联噻吩和三噻吩，其中低聚噻吩尾部垂直或线性连接到束缚羧烷基链，被吸附在 ITO 电极上。在垂直吸附物的情况下，获得的稳定单层在乙腈中被阳极氧化以产生聚合物层（存储 15 μC cm-2 的可逆电荷），而线性联噻吩和三噻吩只能与溶液中的低聚噻吩偶联。电化学和紫外-可见光谱分析表明聚合物层实际上由噻吩六聚体构成。吸附的线性三噻吩可与溶液中的三噻吩本身偶联，以产生一端表面接枝的六噻吩单层（可逆电荷 40 μC cm-2），而具有相同覆盖率的两端表面接枝的六噻吩是通过吸附 α-偶联三噻吩产生的。一端和两端接枝的六噻吩单层显示出不同的电化学...

  DOI：

  10.1021/ja9824728
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 在 正丁基锂 、 一水合肼 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 乙二醇 为溶剂， 反应 5.5h， 生成 环戊联噻吩
  参考文献：
  名称：

  配以钌增感剂和钴电解质的染料敏化太阳能电池的配体工程

  摘要：

  在过去的20年中，基于钌（II）的染料在将染料敏化太阳能电池（DSC）转变为第三代光伏产品的成熟技术方面发挥了关键作用。但是，经典的I 3 – / I –氧化还原对限制了该技术的性能和应用。由于钌（II）敏化剂与钴氧化还原物质之间的相容性差，仅用新型的钴（3 + / 2 +）络合物取代基于碘的氧化还原对就不成功。为了解决此问题并实现更高的功率转换效率（PCE），我们在此介绍通过配体工程开发的六种新的基于环金属化钌（II）的染料。我们测试了使用这些钌（II）配合物的DSC，并使用基于钴（3 + / 2 +）的电解质实现了高达9.4％的PCE，这是迄今为止基于钌的染料的记录效率。鉴于复杂的液体DSC系统，在不同表征之间发现的分歧使我们意识到了TiO2上敏化剂负载的重要性2，这是敏化剂电子特性中的一个微妙但同样重要的因素。

  DOI：

  10.1021/acs.inorgchem.6b00842

文献信息

• An effective strategy to enhance the dielectric constant of organic semiconductors – CPDTTPD-based low bandgap polymers bearing oligo(ethylene glycol) side chains
  作者：Jeroen Brebels、Evgenia Douvogianni、Dries Devisscher、Raghavendran Thiruvallur Eachambadi、Jean Manca、Laurence Lutsen、Dirk Vanderzande、Jan C. Hummelen、Wouter Maes

  DOI：10.1039/c7tc05264b

  日期：——

  dielectric constant (up to εr 6.3) with respect to the reference polymer. Upon applying these materials in bulk heterojunction polymer solar cells, an efficiency of 4.4% is obtained for the best-performing device, with a particularly higher short-circuit current and improved fill factor compared to the pristine alkyl-substituted polymer. Importantly, a non-halogenated solvent – beneficial toward ‘green’

  在有机电子施加的共轭聚合物（特别是光伏和光电检测器）通常表现出相对低的介电常数（ε - [R到光生激子的显著重组损失3-4），其引线。直接的结果是，所产生的设备的性能固有地受到限制。一些努力已指向增加ε - [R光活性有机化合物，但在特定的结构变化对介电常数的影响，并最终装置输出保持的一般知识相当有限。在这项研究中，解决了这个问题。基于4 H-环戊[2,1- b：3,4-合成了一系列的推挽式交替共聚物b ']二噻吩（CPDT）和4 H-噻吩并[3,4- c ]吡咯-4,6（5 H）-二酮（TPD）亚基，目的是通过低聚乙二醇侧提高介电常数链。逐渐增加聚合物主链上乙二醇取代基的数量，以系统地研究其对介电性能的影响。阻抗测量揭示介电常数（高达加倍到ε - [R6.3）相对于参考聚合物。将这些材料应用于本体异质结聚合物太阳能电池后，与原始烷基取代的聚合物相比，性能最佳的器件的效率为4.4％，具有特
• Heteroheptacenes with Fused Thiophene and Pyrrole Rings
  作者：Peng Gao、Don Cho、Xiaoyin Yang、Volker Enkelmann、Martin Baumgarten、Klaus Müllen

  DOI：10.1002/chem.200903562

  日期：——

  over their hydrocarbon counterparts. The analysis of the experimental results from UV/Vis absorption/photoluminescence (PL) spectroscopy and cyclic voltammetry were combined with DFT quantum‐chemical calculations and compared with other model heteroheptacenes. The results suggest that among the acenes with the same number of fused rings, the thiophene ring fusion inside the skeleton stabilizes both HOMO

  报道了使用由超强酸诱导的亲电偶联反应制备共轭杂庚烯的方法。含有噻吩和/或吡咯环的新分子是双苯并[ b，b' ]噻二噻吩并[3,2- b：2'，3'- d ]吡咯，双苯并[ b，b' ]噻吩并环戊[2,1- b ] ：3,4‐ b' ]二噻吩和双歧[3,2‐ b ] thieno [2,3‐ f：5,4‐ f' ]咔唑。Dithieno [3,2‐ b：2′，3′‐ d ]吡咯，环戊a [2,1‐ b：3,4‐ b′]二噻吩和咔唑用作芳族核。这种多功能性使人们可以接近具有系统可控的物理化学性质的分子。X射线单晶分析表明，烷基取代基的类型和位置显着改变了新分子的堆积特性。异庚炔的光学和光电性质根据硫或氮键的数量和位置而有很大不同，并且显示出比其烃对应物更高的环境稳定性。将来自UV / Vis吸收/光致发光（PL）光谱和循环伏安法的实验结果分析与DFT量子化学计算相结合，并与其他模型异庚炔进行了
• Conjugated polymers based on C, Si and N-bridged dithiophene and thienopyrroledione units: synthesis, field-effect transistors and bulk heterojunction polymer solar cells
  作者：Yong Zhang、Jingyu Zou、Hin-Lap Yip、Ying Sun、Josh A. Davies、Kung-Shih Chen、Orb Acton、Alex K.-Y. Jen

  DOI：10.1039/c0jm03927f

  日期：——

  A series of low band-gap conjugated polymers (PDTC, PDTSi and PDTP) containing electron-rich C-, Si-, and N-bridged bithiophene and electron-deficient thienopyrroledione units were synthesized viaStille coupling polymerization. All these polymers possess a low-lying energy level for the highest occupied molecular orbital (HOMO) (as low as −5.44 eV). As a result, photovoltaic devices derived from these polymers show high open circuit voltage (Voc as high as 0.91 V). These rigid polymers also possess respectable hole mobilities of 1.50 × 10−3, 6.0 × 10−4, and 3.9 × 10−4 cm2 V−1s−1 for PDTC, PDTSi, and PDTP, respectively. The combined high Voc and good hole mobility enable bulk hetero-junction photovoltaic cells to be fabricated with relatively high power conversion efficiency (PCE as high as 3.74% for the PDTC-based device).

  通过Stille偶联聚合反应，合成了一系列含有富电子C-、Si-和N-桥联双噻吩以及缺电子噻吩吡咯二酮单元的低带隙共轭聚合物（PDTC、PDTSi和PDTP）。所有这些聚合物都具有较低的最高占据分子轨道（HOMO）能量水平（低至 −5.44 eV）。因此，由这些聚合物衍生出的光伏器件显示出较高的开路电压（Voc高达0.91 V）。这些刚性聚合物还分别具有可观的空穴迁移率，PDTC、PDTSi和PDTP的空穴迁移率分别为1.50 × 10−3、6.0 × 10−4和3.9 × 10−4 cm2 V−1s−1。高Voc和良好的空穴迁移率的结合，使得能够制备出具有相对较高功率转换效率（PCE，PDTC基器件的PCE高达3.74%）的体异质结光伏电池。
• Dithienopyrrole as a Rigid Alternative to the Bithiophene π Relay in Chromophores with Second-Order Nonlinear Optical Properties
  作者：A. Belén Marco、Natalia Martínez de Baroja、Santiago Franco、Javier Garín、Jesús Orduna、Belén Villacampa、Alejandro Revuelto、Raquel Andreu

  DOI：10.1002/asia.201402870

  日期：2015.1

  4H‐Pyranylidene‐containing push‐pull chromophores built around a bithiophene (BT) π relay or a rigidified thiophene‐based unit, namely cyclopenta[1,2‐b:3,4‐b′]dithiophene (CPDT) or dithieno[3,2‐b:2′,3′‐d]pyrrole (DTP), have been synthesized and characterized. The effect of these different relays on the polarization and the second‐order nonlinear optical (NLO) properties has been studied. For the sake of

  4 ħ -Pyranylidene含围绕双噻吩（BT）π继电器或僵化基于噻吩的单元，即环戊二烯并内置推挽生色团[1,2 b：3,4- b ']二噻吩（CPDT）或二噻吩并[已合成并表征了3,2‐ b：2'，3'‐ d ]吡咯（DTP）。研究了这些不同继电器对偏振和二阶非线性光学（NLO）特性的影响。为了比较，报告了相应的dithieno [3,2‐ b：2′，3′‐ d噻吩（DTT）衍生物也已包括在讨论中。用加固单元（CPDT，DTP）替换BT核心会导致极化更多的系统。计算得出的NBO电荷和电化学测量结果表明，二噻吩并吡咯具有显着的施主特性，可以在施主和受主之间进行重要的电荷转移。BT中继的刚性对NLO响应的影响取决于受体强度。对于所使用的最薄弱的受体（硫代巴比妥酸），从BT中继到僵化单元传递总是涉及在增加μβ 0品质因数。然而，对于最强受体（2-二氰基亚甲基-3-氰基-1,4,5,5-三甲基-2
• Molecular engineering of face-on oriented dopant-free hole transporting material for perovskite solar cells with 19% PCE
  作者：Kasparas Rakstys、Sanghyun Paek、Peng Gao、Paul Gratia、Tomasz Marszalek、Giulia Grancini、Kyung Taek Cho、Kristijonas Genevicius、Vygintas Jankauskas、Wojciech Pisula、Mohammad Khaja Nazeeruddin

  DOI：10.1039/c7ta01718a

  日期：——

  Through judicious molecular engineering, novel dopant-free star-shaped D–π–A type hole transporting materials coded KR355, KR321, and KR353 were systematically designed, synthesized and characterized. KR321 has been revealed to form a particular face-on organization on perovskite films favoring vertical charge carrier transport and for the first time, we show that this particular molecular stacking

  通过明智的分子工程，系统地设计，合成和表征了新型无掺杂星形D–π–A型空穴传输材料，其编码为KR355，KR321和KR353。已经发现KR321在钙钛矿薄膜上形成了一个特定的面朝上的组织，这有利于垂直电荷载流子的传输，并且我们首次证明了这种特殊的分子堆叠功能与混合钙钛矿组合使用时可导致功率转换效率超过19％（ FAPbI 3）0.85（MAPbBr 3）0.15。使用没有任何化学添加剂或掺杂的原始空穴传输层获得的19％的效率是最高的，这证明了平面施主核，π间隔基和外围受体的分子工程学导致了高迁移率，并且该设计提供了对以下方面的有用见解用于钙钛矿太阳能电池和光电应用的下一代HTM的合成。