2,5-二溴-噻吩-3,4-二羧酸 | 190723-12-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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: 2,5-二溴-噻吩-3,4-二羧酸
• 中文别名: 2,5-二溴噻吩-3,4-二羧酸
• 英文名称: 2,5-dibromothiophene-3,4-dicarboxylic acid
• 英文别名: 2,5-dibromo-3,4-thiophenedicarboxylic acid
• CAS: 190723-12-7
• 化学式: C₆H₂Br₂O₄S
• 分子量: 329.953
• InChiKey: ZZYYIZHQMCEKLG-UHFFFAOYSA-N

物化性质

• 沸点：
  432.9±45.0 °C(Predicted)
• 密度：
  2.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2,5-Dibromothiophene-3,4-dicarboxylic acid
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2,5-Dibromothiophene-3,4-dicarboxylic acid
CAS number: 190723-12-7

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H2Br2O4S
Molecular weight: 330.0

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide, sulfur oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,5-二溴-噻吩-3,4-二羧酸 在 乙酸酐 作用下， 以96%的产率得到4,6-二溴噻吩并[3,4-C]呋喃-1,3-二酮
  参考文献：
  名称：

  增强有机半导体介电常数的有效策略–基于CPDTTPD的带有低聚乙二醇侧链的低带隙聚合物†

  摘要：

  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

  DOI：

  10.1039/c7tc05264b
• 作为产物：
  描述：

  3,4-噻吩二羧酸 在 溴 、 溶剂黄146 作用下， 以80%的产率得到2,5-二溴-噻吩-3,4-二羧酸
  参考文献：
  名称：

  A D–A copolymer of dithienosilole and a new acceptor unit of naphtho[2,3-c]thiophene-4,9-dione for efficient polymer solar cells

  摘要：

  一种强吸电子单元萘并[2,3-c]噻吩-4,9-二酮与二噻吩硅氧烷共聚，得到一种具有窄带隙和较低HOMO能级的D-A共聚物PDTSNTDO。基于PDTSNTDO的器件的PCE达到5.21%，开路电压高达0.88V。

  DOI：

  10.1039/c1cc14132e

文献信息

• A Facile Synthesized Polymer Featuring B‐N Covalent Bond and Small Singlet‐Triplet Gap for High‐Performance Organic Solar Cells
  作者：Shuting Pang、Zhiqiang Wang、Xiyue Yuan、Langheng Pan、Wanyuan Deng、Haoran Tang、Hongbin Wu、Shanshan Chen、Chunhui Duan、Fei Huang、Yong Cao

  DOI：10.1002/anie.202016265

  日期：2021.4.12

  OSC, comparable to the benzo[1,2‐b:4,5‐b′]dithiophene (BDT)‐based counterpart. The nonradiative recombination energy loss of 0.19 eV was afforded by PBNT‐BDD. PBNT‐BDD also exhibited weak crystallinity and appropriate miscibility with Y6‐BO, benefitting of morphological stability. The singlet–triplet gap (ΔEST) of PBNT‐BDD is as low as 0.15 eV, which is much lower than those of common organic semiconductors

  高效有机太阳能电池（OSC）很大程度上依赖于聚合物供体。在本文中，我们报告了一种新的构建基BNT和具有B-N共价键的相关聚合物PBNT-BDD，可用于OSC。BNT单元仅需3个步骤即可合成，因此可以轻松实现PBNT-BDD的合成。与非富勒烯受体Y6-BO混合时，PBNT-BDD在OSC中的功率转换效率（PCE）为16.1％，与苯并[1,2-b：4,5-b']二噻吩（BDT）相当基于对应项。PBNT-BDD提供的非辐射重组能量损失为0.19 eV。PBNT-BDD还表现出弱结晶性，并与Y6-BO具有适当的混溶性，这有利于形态稳定性。单重态-三重态间隙（ΔE STPBNT-BDD的）低至0.15 eV，远低于常见的有机半导体（≥0.6eV）。结果，PBNT-BDD的三重态高于电荷转移（CT）状态，这将有效地抑制通过三重态的重组。
• Thieno[3,4-<i>c</i> ]pyrrole-4,6-dione-3,4-difluorothiophene Polymer Acceptors for Efficient All-Polymer Bulk Heterojunction Solar Cells
  作者：Shengjian Liu、Zhipeng Kan、Simil Thomas、Federico Cruciani、Jean-Luc Brédas、Pierre M. Beaujuge

  DOI：10.1002/anie.201604307

  日期：2016.10.10

  Branched‐alkyl‐substituted poly(thieno[3,4‐c]pyrrole‐4,6‐dione‐alt‐3,4‐difluorothiophene) (PTPD[2F]T) can be used as a polymer acceptor in bulk heterojunction (BHJ) solar cells with a low‐band‐gap polymer donor (PCE10) commonly used with fullerenes. The “all‐polymer” BHJ devices made with PTPD[2F]T achieve efficiencies of up to 4.4 %. While, to date, most efficient polymer acceptors are based on perylenediimide

  支链烷基取代的聚（噻吩并[3,4- c ^ ]吡咯-4,6- dione- ALT -3,4- difluorothiophene）（PTP-D [2F] T）可以用作在本体异质结的聚合物受体（BHJ ）具有低带隙聚合物供体（PCE10）的太阳能电池，通常与富勒烯一起使用。用PTPD [2F] T制造的“全聚合物” BHJ设备的效率高达4.4％。尽管迄今为止，最有效的聚合物受体是基于per二酰亚胺或萘二酰亚胺基序的，但我们对PTPD [2F] T聚合物的研究表明，具有充分取代的主链的线性全噻吩体系也可能有益于具有聚合物的高效BHJ太阳电池捐助者。
• Benzodithiophene and Imide-Based Copolymers for Photovoltaic Applications
  作者：Wade A. Braunecker、Zbyslaw R. Owczarczyk、Andres Garcia、Nikos Kopidakis、Ross E. Larsen、Scott R. Hammond、David S. Ginley、Dana C. Olson

  DOI：10.1021/cm2038427

  日期：2012.4.10

  Conjugated alternating copolymers were designed with low optical band gaps for organic photovoltaic (OPV) applications by considering quinoid resonance stabilization. Copolymers of thienoisoindoledione (TID) and benzodithiophene (BDT) had appreciably lower band gaps (by ∼0.4 eV) than copolymers of thienopyrroledione (TPD) and BDT. In addition to intramolecular charge transfer stabilization (i.e., the

  考虑到醌型共振稳定性，共轭交替共聚物的光学带隙低，设计用于有机光伏（OPV）应用。噻吩异吲哚二酮（TID）和苯并二噻吩（BDT）的共聚物的带隙（约0.4eV）比噻吩并吡咯二酮（TPD）和BDT的共聚物低得多。除了分子内电荷转移稳定化（即“推挽”效应）外，前者共聚物的醌型共振结构还通过增加异吲哚单元中的芳香族共振能而得以稳定。另外，可以通过对BDT单体进行化学修饰来调节共聚物的HOMO含量，从而在光伏器件中产生大于1 V的开路电压。尽管优化了带隙，但含TID的聚合物仍显示出较低的光电导性，由时间分辨的微波电导率确定，与TPD类似物相比，器件效率降低（2.1％对4.8％）。这些结果部分归因于形态，因为计算模型表明TID共聚物具有扭曲的主链，并且X射线衍射数据表明聚合物膜未形成有序域，而TPD共聚物的平面性明显更高，并显示出形成了部分有序域。 。
• NITROGEN-CONTAINING FUSED RING COMPOUND, NITROGEN-CONTAINING FUSED RING POLYMER, ORGANIC THIN FILM, AND ORGANIC THIN FILM ELEMENT
  申请人：Ie Yutaka

  公开号：US20130041123A1

  公开（公告）日：2013-02-14

  Nitrogen-containing fused ring compound having at least one structural unit selected from the group consisting of a structural unit represented by the formula (1-1) and a structural unit represented by the formula (1-2).

  含氮融合环化合物，其至少具有从由式(1-1)表示的结构单元和由式(1-2)表示的结构单元组成的群体中选择的一个结构单元。
• Enhanced photovoltaic effect from naphtho[2,3-<i>c</i>]thiophene-4,9-dione-based polymers through alkyl side chain induced backbone distortion
  作者：Xiaoman Bi、Tao Zhang、Cunbin An、Pengqing Bi、Kangqiao Ma、Sunsun Li、Kaihu Xian、Qianglong Lv、Shaoqing Zhang、Huifeng Yao、Bowei Xu、Jianqi Zhang、Shaokui Cao、Jianhui Hou

  DOI：10.1039/d0ta02859b

  日期：——

  Two conjugated polymers with different side chain substituted positions were synthesized to study their photovoltaic performances.

  合成了两种具有不同侧链取代位置的共轭聚合物，以研究它们的光伏性能。