2,2-Bi噻吩-5,5-二硼酸 | 189358-30-3

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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
• 中文名称: 2,2-Bi噻吩-5,5-二硼酸
• 英文名称: 2,2'-bithiophene-5,5'-diboronic acid
• 英文别名: 2,2'-bithiophene-5,5'-bis(boronic acid)；[2,2'-Bithiophene]-5,5'-diyldiboronic acid；[5-(5-boronothiophen-2-yl)thiophen-2-yl]boronic acid
• CAS: 189358-30-3
• 化学式: C₈H₈B₂O₄S₂
• 分子量: 253.903
• InChiKey: GERFEEQVJFVEBC-UHFFFAOYSA-N

物化性质

• 沸点：
  575.9±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.16
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,2’-Bithiophene-5,5’-diboronic acid
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 2,2’-Bithiophene-5,5’-diboronic acid
CAS number: 189358-30-3

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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.

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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.

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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.

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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, under −20◦C.
Storage:

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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.

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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: C8H8B2O4S2
Molecular weight: 253.9

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

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,2-Bi噻吩-5,5-二硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.5h， 生成
  参考文献：
  名称：

  发光镧系元素与吡啶-双（羧酰胺）-联噻吩敏化剂的络合物显示出波长依赖性单线态氧的产生。

  摘要：

  合成了一种新的具有双噻吩侧基的吡啶-双（羧酰胺）配体2Tcbx。分离了其镧系离子（LnIII）络合物[Ln（2Tcbx）2] 3+，并研究了其光物理性质。在360 nm激发时，这些络合物在近红外（NIR）中显示发射，LnIII = YbIII的效率为0.69％，LnIII = NdIII的效率为0.20％，LnIII = ErIII的效率为0.01％。所有复合物都可以同时形成1O2，YbIII复合物的效率为19％，NdIII复合物的效率为25％，ErIII复合物的效率为9％。当在更长的波长435 nm处激发时，仅观察到LnIII发射，并且获得了更高的LnIII中心发射效率。缺乏1O2生成表明能量途径涉及不同的配体构象，

  DOI：

  10.1039/d0dt01034k
• 作为产物：
  描述：

  2,2'-联二噻吩 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 生成 2,2-Bi噻吩-5,5-二硼酸
  参考文献：
  名称：

  Preparation and Properties of Rotaxanes Formed by Dimethyl-β-cyclodextrin and Oligo(thiophene)s with β-Cyclodextrin Stoppers

  摘要：

  [graphics]Novel cyclodextrin rotaxanes with oligothiophene as an axis molecule have been prepared by the Suzuki coupling reaction of 6-O-(4-iodophenyl)-beta-CD (6-I-Ph-beta-CD) with di(1,3,2-dioxaborolan-2-yl)-oligothiophene (oligothiophene diboric ethylene glycol esters) in aqueous solutions of dimethyl-beta-cyclodextrin (DM-beta-CD). These reactions gave [2]rotaxanes and [3]rotaxanes, which were isolated by reversed phase chromatography. The fluorescence intensities of rotaxanes are higher than those of dumbbell-shaped molecules (without DM-beta-CD) in aqueous solutions. The inclusion ratio and chain length of rotaxanes have been found to relate to the emission properties and emission intensities of oligothiophene. In aqueous solutions, fluorescence quantum yields of rotaxanes are higher than those of dumbbell-shaped molecules. The increase in the fluorescence efficiency of rotaxane is caused by suppression of intermolecular interactions, indicating the effect of insulated oligothiophene with DM-beta-CD. beta-CD at the both ends of rotaxanes functions not only as bulky stoppers but also as the recognition site for guest molecules, as verified by fluorescence quenching experiments.

  DOI：

  10.1021/jo061834o

文献信息

• Columnar liquid crystalline π-conjugated oligothiophenes
  作者：Takuma Yasuda、Kenji Kishimoto、Takashi Kato

  DOI：10.1039/b606144c

  日期：——

  Polycatenar oligothiophenes possessing three alkoxy chains at each terminal self-organise into columnar liquid crystalline phases, and one-dimensional columnar stacks can be oriented uniaxially by mechanical shearing in the mesophases.

  具有三个烷氧基链的聚链状寡硫烯在每个末端自组织成柱状液晶相，并且一维柱状堆叠可以通过在介相中进行机械剪切进行单轴取向。
• Pluri-dimensional hydrogen-bonded networks of novel thiophene-introduced oligo(imidazole)s and physical properties of their charge-transfer complexes with TCNQ
  作者：Tsuyoshi Murata、Yasushi Morita、Kazuhiro Nakasuji

  DOI：10.1016/j.tet.2005.04.030

  日期：2005.6

  compared with those of 2,2′- and 4,4′-biimidazoles. In the crystal structure, 1, 2 and 3 exhibited multi-dimensional hydrogen-bonded networks via solvent molecules including the π–π interaction. Charge-transfer complexes of 1, 2 and 4 with TCNQ were characterized as partial charge-transfer complexes with segregated stacks. The compressed pellets of the TCNQ complex of 2 showed a high electrical conductivity

  新颖π扩展寡（咪唑）S组成的咪唑和噻吩环系统，双（咪唑基）噻吩1 - 4，合成为新的构建块具有以探讨氢键多样氢键方向性电子给体分子电荷转移络合物和超分子组装体。与2,2'-和4,4'-联咪唑相比，这些化合物的循环伏安法显示了供电子能力的增强。在晶体结构中，1，2和3通过溶剂分子包括π-π相互作用表现多维氢键网络。的电荷转移复合物1，2和4TCNQ的特征是部分电荷转移复合物具有分离的堆叠。的TCNQ复合物的压缩丸粒2显示出高的电导率（σ RT = 5.2×10 -2 小号厘米-1）在室温下与半导体行为（活化能，Ë一个= 71兆电子伏）。
• Helicity Induction in Three π-Conjugated Chromophores by Planar Chirality of Calixamide
  作者：Ryohei Yamakado、Koichiro Mikami、Koji Takagi、Isao Azumaya、Shinri Sugimoto、Shin-ichi Matsuoka、Masato Suzuki、Kosuke Katagiri、Masanobu Uchiyama、Atsuya Muranaka

  DOI：10.1002/chem.201301198

  日期：2013.9.2

  Shall we twist? Three‐dimensional arrangement of π‐conjugated chromophores with triple‐stranded helicity was achieved by using the planar chirality of m‐calix[3]amide (see figure). Based on spectroscopic data and theoretical calculations, the dynamic and preferred helical characters of bithiophene units embedded in the tubular molecule were elucidated, and the absolute configuration was determined

  我们可以扭转吗？通过使用m- calix [3]酰胺的平面手性，实现了具有三链螺旋的π共轭生色团的三维排列。根据光谱数据和理论计算，阐明了嵌入管状分子中的联噻吩单元的动态和优选螺旋特征，并确定了其绝对构型。
• Molecular Design and Preparation of Bis-isophthalate Electrochromic Systems having Controllable Color and Bistability
  作者：W. Sharmoukh、Kyoung Chul Ko、So Yeon Park、Ju Hong Ko、Ji Min Lee、Changho Noh、Jin Yong Lee、Seung Uk Son

  DOI：10.1021/ol802208x

  日期：2008.12.4

  New electrochromic systems based on bis-isophthalates were designed and prepared. They showed electrochromism behavior by two-electron reduction. The displayed colors showed greatly enhanced bistability and were dependent on the length of the conjugated bridge between the two isophthalate groups. We believe that the connection of two electrochromic systems with a conjugated bridge is a good basic strategy to obtain new bistable electrochromic systems.
• Improved stability of organic field-effect transistor performance in oligothiophenes including β-isomers
  作者：Minoru Ashizawa、Takuro Niimura、Yan Yu、Kazuma Tsuboi、Hidetoshi Matsumoto、Ryo Yamada、Susumu Kawauchi、Akihiko Tanioka、Takehiko Mori

  DOI：10.1016/j.tet.2012.02.004

  日期：2012.4

  Dialkyl quarter-and quinquethiophenes end-capped with beta-connected thiophenes are prepared, and the field-effect transistor (FET) properties are investigated. Molecular orbital calculation as well as the redox and optical measurements indicate that the beta-isomers have low-lying HOMO levels and large energy gaps compared with the alpha-isomers. Molecular packing of the dihexylquaterthiophene with beta-isomers consists of a typical herringbone motif analogous to the alpha-isomers. In the single crystal, the alkyl chains are extending in the tilted directions from the core molecular plane, but straightly extending in the thin films, resulting in even more perpendicular molecular arrangement to the substrate than the alpha-isomers. These beta-isomers show p-type FET performance comparable to the corresponding alpha-isomers, whereas all new oligothiophenes show air stability better than the corresponding alpha-isomers. In particular, dihexylquinquethiophene with beta-isomers has shown significantly improved air stability maintained over 270 days. This stabilization effect is ascribed to the low-lying HOMO level and the dense packing realized by perpendicular molecular arrangement. (C) 2012 Elsevier Ltd. All rights reserved.