2,7-二溴-9,9-二(6-溴己基)芴 | 570414-33-4

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 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(6-溴己基)芴
• 中文别名: 9,9-双(6-溴己基)-2,7-二溴芴
• 英文名称: 2,7-dibromo-9,9-bis(6-bromohexyl)fluorene
• 英文别名: 2,7-dibromo-9,9-bis(6-bromohexyl)-9H-fluorene；2,7-dibromo-9,9-di(6-bromohexyl)fluorene
• CAS: 570414-33-4
• 化学式: C₂₅H₃₀Br₄
• 分子量: 650.129
• InChiKey: OJMAUBALNSWGDC-UHFFFAOYSA-N

物化性质

• 熔点：
  70.0 to 74.0 °C
• 沸点：
  612.4±45.0 °C(Predicted)
• 密度：
  1.575±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  应存放在室温、密封且干燥的环境中。

SDS

2,7-Dibromo-9,9-bis(6-bromohexyl)fluorene
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2,7-Dibromo-9,9-bis(6-bromohexyl)fluorene

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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-bis(6-bromohexyl)fluorene
Percent: >98.0%(LC)
CAS Number: 570414-33-4
Chemical Formula: C25H30Br4

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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-bis(6-bromohexyl)fluorene

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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 - Almost white
No data available
Odour:
2,7-Dibromo-9,9-bis(6-bromohexyl)fluorene

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:72°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] No data available

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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:
No data available
IARC =
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
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
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-bis(6-bromohexyl)fluorene

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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(6-溴己基)芴 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 9,9-bis(6'-bromohexyl)-2,7-diethynylfluorene
  参考文献：
  名称：

  带有N 1-烷基胞嘧啶，烷基磷酰基和烷基铵侧链的聚芴：合成，化学性质和对金属离子的感应能力

  摘要：

  聚（9,9-双（6- Ñ 1 -cytosinehexyl）芴-2,7-二基ALT -9,9-双（6'- diethoxyphosphorylhexyl）芴-2,7-二基）（聚合物-1），并聚（9,9-双（6- ñ 1 -cytosinehexyl）芴-2,7-二基ALT -9,9--b，是（6- ñ，ñ，ñ -trimethylammoniumhexyl）芴-2,7-二基通过Pd-络合物催化的缩合反应合成了）（聚合物-2）。在中号ñ和中号w ^通过GPC测定聚合物的百分数。通过紫外可见光，光致发光（PL）和PL寿命测量研究了聚合物对金属离子的传感行为。聚合物PL随添加金属离子（例如Cu +，Cu 2 +，Pd 2 +，Ag +和Pt 2+）而降低，而在添加Na +和Fe 3+时几乎保持不变。添加金属离子后PL强度的降低很可能是由于胞嘧啶基团与金属络合导致聚合物聚集而引起的。聚合物的循环伏安法分析显示了它们的电化学活性。

  DOI：

  10.1016/j.reactfunctpolym.2021.104900
• 作为产物：
  描述：

  芴 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 氢溴酸 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 生成 2,7-二溴-9,9-二(6-溴己基)芴
  参考文献：
  名称：

  Decoration of Polyfluorene-Wrapped Carbon Nanotubes with Photocleavable Side-Chains

  摘要：

  通过铜催化叠氮-炔烃环加成（CuAAC）技术，可以在不破坏聚芴包裹的碳纳米管特性的情况下对其进行功能化。然而，聚合物侧链的长度和性质会阻碍纳米管之间的紧密接触，从而影响聚芴-SWNT 薄膜的导电性。在此，我们研究了利用可在加工后去除的光可裂解侧链对聚芴-SWNT 复合物进行功能化的方法。当暴露在 365 纳米波长的紫外灯下时，含有邻硝基苄基醚衍生物的侧链会被有效地裂解。我们首先通过聚合物的紫外可见吸收光谱和 1H-NMR 光谱监测了邻硝基苯醚连接体光异构化为相应的邻硝基苯甲醛的过程，结果表明 2 小时后裂解效率很高。纳米管分散体的沉淀和隔夜辐照后的宽吸收峰也表明了裂解的有效性。此外，辐照后的拉曼光谱显示，纳米管在辐照后并未受损。本文报告了一个概念验证，该概念验证可能会应用于基于 SWNT 的材料，其中侧链的去除可能会带来更高的设备性能。

  DOI：

  10.3390/molecules28031471

文献信息

• An ultra-highly sensitive and selective self-enhanced AIECL sensor for public security early warning in a nuclear emergency <i>via</i> a co-reactive group poisoning mechanism
  作者：Ziyu Wang、Meiyun Xu、Nan Zhang、Jian-Bin Pan、Xinqi Wu、Peng Liu、Jing-Juan Xu、Daoben Hua

  DOI：10.1039/d1ta02158c

  日期：——

  A mechanism of co-reactive group poisoning (CGP) was discovered for designing efficient I₂ vapor sensors for early warning of a nuclear emergency, which give an ultra-low detection limit of 0.13 ppt as well as high selectivity.

  发现了一种共反应基团中毒（CGP）机制，用于设计高效的I2蒸汽传感器，以实现核紧急情况早期预警，该传感器具有超低检测限0.13 ppt以及高选择性。
• A novel crosslinkable electron injection/transporting material for solution processed polymer light-emitting diodes
  作者：ShengJian Liu、ChengMei Zhong、Jie Zhang、ChunHui Duan、XiaoHui Wang、Fei Huang

  DOI：10.1007/s11426-011-4386-8

  日期：2011.11

  A novel crosslinkable water/alcohol soluble conjugated polymer PFN-C containing oxetane groups and aminoalkyl groups in the side chains has been developed and used as highly efficient electron injection and transporting material for polymer light-emitting diodes (PLEDs). The unique solubility in polar solvents and crosslinkable ability of PFN-C render it a good candidate for solution processed multilayer PLEDs. It was found that PFN-C can greatly enhance the electron injection from high work-function metal cathode, due to its pendant amino groups. As a result, PLEDs with PFN-C/Al cathode exhibited comparable device performance to the devices with Ba/Al cathode. The resulting green light-emitting device showed promising performance with a maximum luminance efficiency of 13.53 cd A−1.

  开发了一种新型的可交联水/醇溶解的共轭聚合物PFN-C，其侧链中含有环氧烷基和氨基烷基。该聚合物被用作高效的电子注入和传输材料，适用于聚合物发光二极管（PLEDs）。PFN-C在极性溶剂中的独特溶解性和可交联能力使其成为适合于溶液处理的多层PLEDs的良好候选材料。研究发现，PFN-C能够显著增强来自高功函数金属阴极的电子注入，这得益于其侧链的氨基基团。因此，采用PFN-C/铝阴极的PLEDs显示出与采用钡/铝阴极的器件相当的性能。最终生成的绿色发光器件显示出令人振奋的性能，最高光效为13.53 cd A−1。
• Phosphine oxide-functionalized polyfluorene derivatives: Synthesis, photophysics, electrochemical properties, and electroluminescence performance
  作者：ZengShan Guo、DeAng Liu、Cheng Wang、Jian Pei、ZhangLin Zhou、LiHua Zhao、Gary Gibson、James Brug、Sity Lam、Samuel S. Mao

  DOI：10.1007/s11426-011-4249-3

  日期：2011.4

  A series of phosphine oxide-functionalized polyfluorene derivatives, PFH-PO-40-1 (P1), PFH-PO-20-1 (P2), PFH-PO-10-1 (P3), and PFH-PO-1-1 (P4), were prepared via a palladium-mediated Suzuki cross-coupling reaction. The structures and purities of all polymers were fully characterized by 1H and 13C NMR, UV-vis and photoluminescent spectroscopy, gel permeation chromatography, and TGA/DSC. Their emission features showed single broad peaks at about 445 nm in film, compared with those in dilute solutions, which might be caused by some degree of aggregation in the excited states of the backbones. The best electroluminescence (EL) performance of these polymers with configuration of ITO/PEDOT:PSS/Polymer/Alq3/LiF/Al was obtained from P1 (current efficiency was 4.2 Cd/A at 6V).

  一系列磷烷氧化物功能化的聚氟烯衍生物，PFH-PO-40-1 (P1)、PFH-PO-20-1 (P2)、PFH-PO-10-1 (P3)和PFH-PO-1-1 (P4)，通过钯介导的铃木交叉偶联反应制备。所有聚合物的结构和纯度均通过核磁共振（1H和13C NMR）、紫外-可见光谱和光致发光光谱、凝胶渗透色谱和热重分析/差示扫描量热法（TGA/DSC）进行了全面表征。它们的发射特征在薄膜中显示出约445 nm的单一宽峰，而在稀溶液中则有所不同，这可能是由于主链在激发态下发生了一定程度的聚集。这些聚合物在ITO/PEDOT:PSS/聚合物/Alq3/LiF/Al构型下获得的最佳电致发光（EL）性能是来自P1（在6V时电流效率为4.2 Cd/A）。
• Solubility Modulation of Polyfluorene Emitters by Thermally Induced (Retro)-Diels–Alder Cross-Linking of Cyclopentadienyl Substituents
  作者：Lukas Ahrens、Stefan Schlisske、Karl-Philipp Strunk、Felix Hinkel、Christian Melzer、Uwe H. F. Bunz、Uli Lemmer、Gerardo Hernandez-Sosa、Daniel Jänsch、Jan Freudenberg、Klaus Müllen

  DOI：10.1021/acs.chemmater.8b01703

  日期：2018.6.26

  devices, the consecutive deposition of active layers by solution-based processes is a key benefit. We report a synthetic approach enabling solubility reduction of bis(cyclopentadienyl)-substituted polyfluorenes as emissive layers in organic light-emitting diodes (OLEDs). Thermally induced retro-Diels–Alder reaction liberates free cyclopentadiene as “protecting group” and pending cyclopentadienyl units

  对于具有成本效益的有机电子设备，通过基于溶液的工艺连续沉积有源层是一个关键优势。我们报告了一种合成方法，该方法能够降低双（环戊二烯基）取代的聚芴作为有机发光二极管（OLED）中的发光层的溶解度。热诱导的逆Diels-Alder反应释放出游离的环戊二烯作为“保护基”和未决的环戊二烯基单元，这些单元通过[4 + 2]环加成反应冷却后可将聚合物链交联。通过烷基，烷氧基或酯键，可以将活化温度调节在180–250°C的范围内。最终，大环自我保护的双（环戊二烯）部分避免了活化过程中挥发性环戊二烯的挤出。通过吸收光谱法和白光扫描干涉法检查交联后的发光层的耐溶剂性。研究了增溶过程对溶液加工的OLED性能的影响。
• π-Conjugated polymers with pendant coumarins: design, synthesis, characterization, and interactions with carbon nanotubes
  作者：Mokhtar Imit、Patigul Imin、Alex Adronov

  DOI：10.1139/cjc-2016-0205

  日期：2016.9

  polyfluorene backbone was efficient, especially for the polymers decorated with lower-generation dendrons. Each of the polymers was found to interact strongly with the surface of single-walled carbon nanotubes (SWNTs) in THF, and their ability to selectively disperse specific SWNT chiralities was investigated. Photoluminescence studies revealed that the strong polymer emission is efficiently quenched in the

  使用 Suzuki-Miyaura 交叉偶联反应设计和制备了一系列具有香豆素衍生物作为树枝状侧链一部分的新型芴基 π 共轭聚合物。使用带有用于溶解性的庚基侧链的新香豆素衍生物来确保最终聚合物的溶解性。发现从香豆素到聚芴骨架的荧光共振能量转移 (FRET) 是有效的，特别是对于用低代树枝状修饰的聚合物。发现每种聚合物都与 THF 中的单壁碳纳米管 (SWNT) 的表面发生强烈相互作用，并研究了它们选择性分散特定 SWNT 手性的能力。光致发光研究表明，在与 SWNT 相应的超分子复合物中，强聚合物发射被有效地淬灭。这种高猝灭效率表明香豆素-聚合物 FRET 系统可以超分子地结合到 (SWNTs 的表面以产生烯...