2,7-二溴-9,9-二癸基芴 | 175922-78-8

• 物质功能分类: 化学试剂 - 有机试剂 - 芳烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,7-二溴-9,9-二癸基芴
• 中文别名: 2,7-二溴-9,9-二癸芴；9,9-二癸基-2,7-二溴芴
• 英文名称: 2,7-dibromo-9,9-didecylfluorene
• 英文别名: 2,7-dibromo-9,9-didecyl-9H-fluorene；2.7-dibromo-9,9-di-n-decyl-9H-fluorene
• CAS: 175922-78-8
• 化学式: C₃₃H₄₈Br₂
• 分子量: 604.552
• InChiKey: RLYANTSRYXOALQ-UHFFFAOYSA-N

物化性质

• 熔点：
  38.0 to 42.0 °C
• 沸点：
  610.3±48.0 °C(Predicted)
• 密度：
  1.166
• 溶解度：
  溶于四氢呋喃

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903999090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319

SDS

2,7-Dibromo-9,9-didecylfluorene
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2,7-Dibromo-9,9-didecylfluorene
5.3

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2,7-Dibromo-9,9-didecylfluorene
Percent: >98.0%(HPLC)(T)
CAS Number: 175922-78-8
Chemical Formula: C33H48Br2

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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.
2,7-Dibromo-9,9-didecylfluorene

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. 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.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
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.
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
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
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
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
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 cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
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.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
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
Crystal- Powder
Form:
Colour: White - Pale yellow
No data available
Odour:
2,7-Dibromo-9,9-didecylfluorene

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:40°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Tetrahydrofuran(THF)

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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, Hydrogen bromide
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
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
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
2,7-Dibromo-9,9-didecylfluorene

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,7-二溴-9,9-二癸基芴 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  共轭聚合物在主链上带有咔唑，芴和亚乙基二氧噻吩并带有氰基侧基：合成，光物理和电化学研究

  摘要：

  经由Sonogashira偶联聚合反应，已经设计并合成了六种新的共轭聚合物，这些聚合物沿着主链具有由咔唑，芴和亚乙基二氧噻吩（EDOT）部分组成，并且侧基带有连接到乙烯部分的氰基。光学和电化学表征表明，能带隙在2.35–2.44 eV范围内。此外，咔唑和EDOT的存在使这些聚合物成为更好的空穴传输材料，这可从循环伏安图中的低氧化电位峰（0.55-1.11 V）反映出来。此外，与原始THF相比，在90:10 THF /水混合物中，聚集增强发射（AEE）现象导致荧光强度增加了2.6倍。通过DLS（动态光散射）实验和SEM（扫描电子显微镜）研究进一步验证了AEE特性。溶液中以及聚苯乙烯基质中的聚合物在绿色区域发射（溶液状态Φ下的量子产率）f = 41–43％）的CIE值（0.25–0.36、0.52-0.57）。新型聚合物具有出色的热稳定性。©2016 Wiley Periodicals，Inc

  DOI：

  10.1002/pola.28160
• 作为产物：
  描述：

  芴 在 溴 、 sodium hydroxide 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 生成 2,7-二溴-9,9-二癸基芴
  参考文献：
  名称：

  共轭聚合物在主链上带有咔唑，芴和亚乙基二氧噻吩并带有氰基侧基：合成，光物理和电化学研究

  摘要：

  经由Sonogashira偶联聚合反应，已经设计并合成了六种新的共轭聚合物，这些聚合物沿着主链具有由咔唑，芴和亚乙基二氧噻吩（EDOT）部分组成，并且侧基带有连接到乙烯部分的氰基。光学和电化学表征表明，能带隙在2.35–2.44 eV范围内。此外，咔唑和EDOT的存在使这些聚合物成为更好的空穴传输材料，这可从循环伏安图中的低氧化电位峰（0.55-1.11 V）反映出来。此外，与原始THF相比，在90:10 THF /水混合物中，聚集增强发射（AEE）现象导致荧光强度增加了2.6倍。通过DLS（动态光散射）实验和SEM（扫描电子显微镜）研究进一步验证了AEE特性。溶液中以及聚苯乙烯基质中的聚合物在绿色区域发射（溶液状态Φ下的量子产率）f = 41–43％）的CIE值（0.25–0.36、0.52-0.57）。新型聚合物具有出色的热稳定性。©2016 Wiley Periodicals，Inc

  DOI：

  10.1002/pola.28160

文献信息

• Electroactive and luminescent polymers: new fluorene-heterocycle-based hybrids
  作者：Barbara Tsuie、Jerry L. Reddinger、Gregory A. Sotzing、Jadwiga Soloducho、Alan R. Katritzky、John R. Reynolds

  DOI：10.1039/a903374b

  日期：——

  The synthesis, characterization, and electrochromic properties of copolymers derived from 9,9-dialkyl-2,7-dibromofluorene (18a, alkyl=C 10 H 21 ; 24, alkyl=Et) and pyrrole, thiophene, 3,4-ethylenedioxythiophene, and furan are described. Two synthetic routes to 9,9-diethyl-2,7-bis(pyrrol-2-yl)fluorene (30) afford product in 30% and 20% yields, respectively. Monomer 30 undergoes electropolymerizationto yield electroactive polymer films. The lowest monomer oxidation potential (E p,m =0.4 V vs. Ag/Ag + ) is found in tetraethylammonium tosylate (TEATOS)-CH 3 CN, but film formation is slow. Spectroelectrochemical analysis of poly(30) reveals a band gap at 2.4 eV and upon polymer oxidation, two low energy absorptions peaking at 1.2 and 2.2 eV appear. This phenomenon is attributed to formation of bipolaron bands between the valence and conduction bands. Soluble fluorene-heterocycle polymers 34a-d have been synthesized by the Stille coupling reaction of 18a and 2,5-bis(trimethylstannyl)thiophene (21a), 5,5′-bis(trimethylstannyl)-2,2′-bithiophene (21b), 2,5-bis(trimethylstannyl)-3,4-ethylenedioxythiophene (21c), and 2,5-bis(trimethylstannyl)furan (22), respectively, in high yields. The NMR spectra are consistent with the proposed structures of the polymers 34a-d, and no evidence of ring opening of the furyl unit in 34d is seen in the NMR and IR spectra. The molecular weights of 34a-d are in the range of 8000 g mol –1 with polydispersity indices (PDI) of 2. Polymers 34a-c have band gaps measured at 2.4 eV, while polymer 34d has its gap at 2.6 eV. Polymers 34a-c undergo solution doping with SbCl 5 to form new low energy bipolaron bands at the expense of the absorption in the UV-VIS. However, polymer 34d does not oxidatively dope with SbCl 5 .

  描述了从9,9-二烷基-2,7-二溴芴（18a，烷基=C10H21；24，烷基=Et）和吡咯、噻吩、3,4-亚乙基二氧噻吩以及呋喃衍生的共聚物的合成、表征和电致变色性质。两条合成9,9-二乙基-2,7-双（吡咯-2-基）芴（30）的路线分别获得了30%和20%的产率。单体30经电化学聚合生成电活性聚合物薄膜。最低单体氧化电位（Ep,m=0.4 V vs. Ag/Ag+）在四乙基铵对甲苯磺酸盐（TEATOS）-CH3CN中观察到，但薄膜形成缓慢。光谱电化学分析发现聚30的带隙为2.4 eV，聚合物氧化后出现两个低能量吸收峰，峰值为1.2 eV和2.2 eV，这一现象归因于价带和导带之间双极化子带的形成。通过Stille偶联反应，18a分别与2,5-双（三甲基锡基）噻吩（21a）、5,5′-双（三甲基锡基）-2,2′-双噻吩（21b）、2,5-双（三甲基锡基）-3,4-亚乙基二氧噻吩（21c）和2,5-双（三甲基锡基）呋喃（22）反应，合成了可溶性芴-杂环聚合物34a-d，产率较高。NMR光谱与所提出的聚合物34a-d的结构一致，NMR和IR光谱中未观察到34d中呋喃单元的开环证据。34a-d的分子量在8000 g mol–1范围内，多分散性指数（PDI）为2。聚合物34a-c的带隙测得为2.4 eV，而聚合物34d的带隙为2.6 eV。聚合物34a-c通过溶液掺杂SbCl5形成新的低能量双极化子带，以牺牲紫外-可见光吸收为代价。然而，聚合物34d不能通过SbCl5进行氧化掺杂。
• PIPERAZINE-CONTAINING TWO-PHOTON ABSORBING COMPOUNDS
  申请人：Government of the United States, as represented by the Secretary of the Air Force

  公开号：US20180273524A1

  公开（公告）日：2018-09-27

  A two-photon absorbing (TPA) compound is provided along with a method of making same. The TPA compound has a general structural formula: where R 1 and R 2 are independently selected from the group consisting of linear or branched alkyl chains having a general formula C n H 2n+1 , n ranges from about 6 to about 20, and ethoxylated alkyls having a general formula R 3 (OCH 2 CH 2 ) m OCH 2 CH 2 —, where R 3 is a C1 to C4 alkyl group, and where m ranges from 0 to about 3; and where Y is selected from the group consisting of H, OH, and alkoxyl groups.

  提供了一种双光子吸收（TPA）化合物以及制备方法。该TPA化合物具有一般结构式：其中R1和R2分别选自由一般式CnH2n+1的线性或支链烷基链组成的群，n范围约为6到20，以及具有一般式R3（OCH2CH2）mOCH2CH2—的乙氧基化烷基，其中R3是C1到C4烷基基团，m范围约为0到3；Y选自H、OH和烷氧基团组成的群。
• Two-photon absorption and polymerization ability of intramolecular energy transfer based photoinitiating systems
  作者：Ming Jin、Jean-Pierre Malval、Davy-Louis Versace、Fabrice Morlet-Savary、Hélène Chaumeil、Albert Defoin、Xavier Allonas、Jean-Pierre Fouassier

  DOI：10.1039/b808457b

  日期：——

  We design a new photoinitiating system where the two-photon absorption of a 2,7 bisaminofluorene moiety leads to the photoactivation of a camphorquinone subunit through a Förster-type intramolecular energy transfer: the application to a two-photon polymerization reaction is demonstrated.

  我们设计了一种新的光引发系统，其中2,7-二氨基荧光烯（bisaminofluorene）部分的双光子吸收通过Förster型分子内能量转移激活了樟脑醌亚基，展示了其在双光子聚合反应中的应用。
• Photoinduced intramolecular electron transfer in a 2,7-diaminofluorene chromophore decorated with two benzophenone subunits
  作者：Ming Jin、Jean-Pierre Malval、Fabrice Morlet-Savary、Hélène Chaumeil、Albert Defoin、Pinar Batat、Gediminas Jonusauskas

  DOI：10.1039/b813717j

  日期：——

  respect to that of the model one. A photoinduced intramolecular electron transfer (PIET) from diaminofluorene to benzophenone subunits is proposed as the most efficient quenching process. At low polar solvent, the emission of an exciplex confirms the PIET process and the occurrence of a partial charge separation between donor and acceptor parts.

  提出了与两个二苯甲酮部分共价连接的2,7-双-（N -4-甲氧基苯基-N-苯基氨基）芴衍生物的广泛的光物理分析。与不带模型发色团的系统比较二苯甲酮被执行了。对于两种生色团，基态的电子性质完全相等，表明二苯甲酮亚基与二氨基芴核没有任何电子相互作用。但是，在单重态下，二苯甲酮的存在会引起其他非辐射去激励途径的发生。相对于模型一，甚至系统间的交叉速率也显着提高。光致分子内电子转移（PIET）二氨基芴二苯甲酮亚基被认为是最有效的淬灭方法。在低极性溶剂下，激基复合物的发射证实了PIET过程以及施主和受主部分之间的部分电荷分离。
• Branched Oligoarylsilanes and Method for Producing Same
  申请人："LUMINESCENT INNOVATION TECHNOLOGIES" LIMITED LIABILITY COMPANY

  公开号：US20160108065A1

  公开（公告）日：2016-04-21

  Novel branched oligoarylsilanes of general formula (I) A method of preparation of branched oligoarylsilanes is that a compound of general formula (III) Y-Q k -SiAr n —R) 3 (III), where Y stands for a residue of boronic acid or its ester or Br or I, reacts under Suzuki conditions with a reagent of general formula (IV) A-X m -A (IV), where A stands for: Br or I, provided that Y stands for a residue of boronic acid or its ester; or a residue of boronic acid or its ester, provided that Y stands for Br or I. A technical result is preparation of novel compounds, featured by a high luminescence efficiency, efficient intramolecular energy transfer from some molecular fragments to others, and an increased thermal stability.

  通用公式（I）的新型分支寡芳基硅烷的翻译如下： 一种制备分支寡芳基硅烷的方法是，通式（III）Y-Qk-SiArn—R)3(III)的化合物，在Suzuki条件下与通式（IV）A-Xm-A(IV)的试剂发生反应，其中Y代表硼酸或其酯或Br或I的残基，A代表Br或I，条件是Y代表硼酸或其酯的残基；或硼酸或其酯的残基，条件是Y代表Br或I。技术上的结果是制备具有高发光效率、分子片段之间高效内分子能量转移以及增加热稳定性的新型化合物。