9,9-二辛基-9H-9-硅杂芴-2,7-双(硼酸频哪醇酯) | 958293-23-7

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 9,9-二辛基-9H-9-硅杂芴-2,7-双(硼酸频哪醇酯)
• 英文名称: 5,5-dioctyl-3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-dibenzo[b,d]silole
• 英文别名: 2-[5,5-dioctyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b][1]benzosilol-7-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 958293-23-7
• 化学式: C₄₀H₆₄B₂O₄Si
• 分子量: 658.653
• InChiKey: QLOFNQWFMMGWBX-UHFFFAOYSA-N

物化性质

• 熔点：
  115-120℃
• 沸点：
  701.3±60.0 °C(Predicted)
• 密度：
  1.01

计算性质

• 辛醇/水分配系数(LogP)：
  8.55
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 9,9-Dioctyl-9H-9-silafluorene-2,7-bis(boronic acid
pinacol ester)
CAS-No. : 958293-23-7
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H -9-
silafluorene
5,5-Dioctyl-3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H -
dibenzo[b,d]silole
Formula : C40H64B2O4Si
Molecular Weight : 658,64 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Borane/boron oxides, silicon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Light sensitive.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 115 - 120 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion
May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  9,9-二辛基-9H-9-硅杂芴-2,7-双(硼酸频哪醇酯) 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 66.0h， 生成 8-[4-[4-[3-[4-[4-(8-Hydroxyoctoxy)phenyl]phenyl]-5,5-dioctylbenzo[b][1]benzosilol-7-yl]phenyl]phenoxy]octan-1-ol
  参考文献：
  名称：

  [EN] DIBENZO[D,B]SILOLE-BASED REACTIVE MESOGENS
  [FR] MÉSOGÈNES RÉACTIFS À BASE DE DIBENZO[D,B]SILOLE

  摘要：

  本发明提供了一种化合物，其化学式为（I）D-S1-A-S2 B1，其中化学式（I）中的a代表一个由1到20个芳香基团组成的共轭链，这些芳香基团可以独立地选自芳香基团、杂芳基团和E基团的组合，其中A至少包括一个E基团，其中E选自包括结构为dibenzo[d,b]硅烯基团的E1、结构为E2的基团和结构为E3的基团的组合，其中E连接在A的共轭链中，并且可以通过在Y和Z处与S1或S2形成共价键连接；其中每个R可以独立地选自直链或支链的C1-C20烷基和C2-C20烯基的组合，可选地，其中从1到5个CH2基团中的每个都被氧替代，前提是R基团中没有存在缩醛、缩酮、过氧化物或乙烯醚，并且每个连接到R基团中的C的H可以独立地被卤素替代；其中X基团相同，选自氢、直链或支链的C1-C8烷基、直链或支链的C1-C8烷氧基和卤素，每个E基团可能具有相同或不同的X基团，W为氧或硫原子，D代表具有一个或多个可交联官能团的基团，S1和S2是柔性连接基团；B1代表具有一个或多个可交联官能团或氢原子的基团，但有一个条件，即当B1代表氢原子时，D代表至少具有两个可交联官能团的基团。

  公开号：

  WO2018065786A1
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 盐酸 、 tin 、 叔丁基锂 、 铜 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.83h， 生成 9,9-二辛基-9H-9-硅杂芴-2,7-双(硼酸频哪醇酯)
  参考文献：
  名称：

  The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics

  摘要：

  对共轭聚合物的结构-功能关系的理解是成功设计用于有机电子器件的新材料的重要资源。为此，我们报道了一系列新的交替共聚物的合成、表征和光电特性，这些聚合物基于二苯硅烯。通过铃木聚合反应，我们合成了一系列八种共轭材料，它们是将3,6-或2,7-连接的9,9-二辛基二苯硅烯与3,6-连接的N-辛基卡巴唑、三芳胺、噁二唑和三唑单体相结合而得到的。我们使用1H和13C{1H} NMR光谱、尺寸排斥色谱（SEC）、差示扫描量热法（DSC）和热重分析（TGA）对共聚物进行了全面表征。利用紫外-可见光光谱、光致发光（PL）测量、循环伏安法（CV）和空气中的光电子发射光谱（PESA）确定了光物理性质。通过这些光谱和电化学测量，我们确定了材料的HOMO和LUMO能量，并将这些值与共聚物的组成和结构相关联。选择的共聚物（P4、P5和P8）作为单层聚合物发光二极管（PLEDs）的活性层进行评估，配置为：玻璃/ITO/PEDOT:PSS/发光层/Ba/Al，结果显示出低强度的电致发光。这些选定的共聚物也作为底栅、底接触有机场效应晶体管（OFETs）的有机半导体进行评估。表现最好的器件达到了最高的迁移率3 × 10−4 cm2 V−1s−1和开关电流比105。

  DOI：

  10.1039/c1jm11242b

文献信息

• 双（S,S-二氧-二苯并噻吩）并五元环化合物及 其制备方法与应用
  申请人：华南理工大学

  公开号：CN105017302B

  公开（公告）日：2019-06-18

  本发明公开双（S,S‑二氧‑二苯并噻吩）并五元环化合物及其制备方法与应用。所述双S,S‑二氧二苯并噻吩并五元环中双砜基的存在更加有利于提高分子的电子亲和势。在五元环上引入烷基链可以显著改善单体在有机溶剂中的溶解性。化合物的平面共轭性较好，有利于载流子的传输。化合物分子内存在较强的D‑A相互作用赋予材料较好的荧光性。双S,S‑二氧‑二苯并噻吩并五元环化合物通过取代反应、Suzuki偶联、闭环反应和氧化反应等常用有机化学反应合成得到。化合物在有机溶剂中有良好的溶解性，适合于溶液加工。在有机发光显示、有机光伏电池以及有机场效应管领域有着广泛的应用前景。
• Silole‐containing polymers for high‐efficiency polymer solar cells
  作者：Jinsheng Song、Chun Du、Cuihong Li、Zhishan Bo

  DOI：10.1002/pola.24870

  日期：2011.10

  Silole‐containing conjugated polymers (P1 and P2) carrying methyl and octyl substituents, respectively, on the silicon atom were synthesized by Suzuki polycondensation. They show strong absorption in the region of 300–700 nm with a band gap of about 1.9 eV. The two silole‐containing conjugated polymers were used to fabricate polymer solar cells by blending with PC61BM and PC71BM as the active layer

  通过铃木缩聚反应合成了分别在硅原子上带有甲基和辛基取代基的含硅共轭聚合物（P1和P2）。它们在300-700 nm范围内显示出强吸收，带隙约为1.9 eV。通过与PC 61 BM和PC 71 BM混合作为活性层，使用了两种含硅烷的共轭聚合物来制造聚合物太阳能电池。基于P1 / PC 71 BM有源层的光伏器件的最佳性能表现出2.72％的功率转换效率（PCE），而使用P2 / PC 71制造的光伏电池则具有更高的功率转换效率（PCE）。BM的PCE为5.08％。1,8-二碘辛烷用作添加剂，可在器件优化过程中调节有源层的形貌。当使用TiO x层作为空穴阻挡层时，基于P2 / PC 71 BM的器件的PCE进一步提高到6.05％。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年
• Low Bandgap Polymers Based on Silafluorene Containing Multifused Heptacylic Arenes for Photovoltaic Applications
  作者：Mingjian Yuan、Pinyi Yang、Matthew M. Durban、Christine K. Luscombe

  DOI：10.1021/ma300839c

  日期：2012.8.14

  A series of donor–acceptor copolymers based on a new silafluorene containing multifused heptacylic arenes have been designed and synthesized in order to further modulate and optimize their electronic and optical properties. Polymer solar cells based on a blend of these polymers and PC61BM exhibited high open circuit voltages of up to 0.86 V. Through simple and straightforward engineering of molecular

  为了进一步调节和优化其电子和光学性能，已经设计和合成了一系列基于一种新型的含有多融合七环芳烃的硅芴的供体-受体共聚物。基于这些聚合物和PC 61 BM的混合物的聚合物太阳能电池表现出高达0.86 V的高开路电压。通过分子结构的简单直接设计，基于PSiFDCTBT：PC 61 BM（1：3.5 in wt平均提供的V oc为0.86 V，J sc为8.8 mA / cm 2，FF为56％，PCE为4.2％。
• Synthesis and Photophysical Properties of Silole-Fused Cycloparaphenylenes
  作者：Yedong Wang、Shiqing Huang、Zengyu Zhang、Xiaoyu Yan

  DOI：10.1021/acs.joc.3c01323

  日期：2024.1.5

  Herein, we report the introduction of a silole unit into cycloparaphenylenes (CPPs), and two compounds [12]Si3CPP and [16]Si4CPP are obtained by a platinum- and gold-mediated cyclooligomerization strategy. Their optical and electronic properties are studied by UV–vis absorption and fluorescence spectra, which show red shifts and higher photoluminescence quantum yields (PLQYs) compared with the corresponding

  在此，我们报道了将噻咯单元引入环对亚苯基（CPP）中，并通过铂和金介导的环齐聚策略获得了两种化合物[12]Si 3 CPP和[16]Si 4 CPP 。通过紫外可见吸收和荧光光谱研究了它们的光学和电子特性，与相应的 CPP 相比，这些光谱显示出红移和更高的光致发光量子产率 (PLQY)。
• Synthesis, Characterization, and Transistor Response of Semiconducting Silole Polymers with Substantial Hole Mobility and Air Stability. Experiment and Theory
  作者：Gang Lu、Hakan Usta、Chad Risko、Lian Wang、Antonio Facchetti、Mark A. Ratner、Tobin J. Marks

  DOI：10.1021/ja800424m

  日期：2008.6.18

  Realizing p-channel semiconducting polymers with good hole mobility, solution processibility, and air stability is an important step forward in the chemical manipulation of charge transport in polymeric solids and in the development of low-cost printed electronics. We report here the synthesis and full characterization of the dithienosilole- and dibenzosilole-based homopolymers, poly(4,4-di-n-hexyldithienosilole) (TS6) and poly(9,9-di-n-octyldibenzosilole) (BS8), and their mono- and bithiophene copolymers,, poly(4,4-di-n-hexyldithienosilole-alt-(bi)thiophene) (TS6T1,TS6T2) and poly(9,9-di-n-octyldibenzosilole-alt(bi)thiophene) (BS8T1,BS8T2), and examine in detail the consequences of introducing dithienosilole and dibenzosilole cores into a thiophene polymer backbone. We demonstrate air-stable thin-film transistors (TFTs) fabricated under ambient conditions having hole mobilities as large as 0.08 cm(2)/V.s, low turn-on voltages, and current on/off ratios > 10(6). Additionally, unencapsulated TFTs fabricated under ambient conditions are air-stable, an important advance over regioregular poly(3-hexylthiophene) (P3HT)-based devices. Density functional theory calculations provide detailed insight into the polymer physicochemical and charge transport characteristics. A direct correlation between the hole injection barrier and both TFT turn-on voltage and TFT polymer hole mobility is identified and discussed, in combination with thin-film morphological characteristics, to explain the observed OTFT performance trends.