α,ω-二己基四噻吩 5,5′-双(3-己基-2-噻吩基)-2,2′-联噻吩 | 132814-91-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 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: α,ω-二己基四噻吩 5,5′-双(3-己基-2-噻吩基)-2,2′-联噻吩
• 中文别名: 3,3′′′-二己基-2,2′:5′,2′′:5′′,2′′′-四噻吩；α,ω-二己基四噻吩5,5′-双(3-己基-2-噻吩基)-2,2′-联噻吩；3,3'''-二己基-2,2':5',2'':5'',2'''-四噻吩
• 英文名称: 3,3'-dihexyl-2,2':5',2:5,2'-quarterthiophene
• 英文别名: 3,3'''-dihexyl-2,2':5',2'':5'',2'''-quaterthiophene；2-(3-hexylthiophen-2-yl)-5-[5-(3-hexylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 132814-91-6
• 化学式: C₂₈H₃₄S₄
• 分子量: 498.842
• InChiKey: MLDVGCCQHBDHDR-UHFFFAOYSA-N

物化性质

• 熔点：
  25-29 °C
• 沸点：
  592.0±50.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)
• 闪点：
  110 °C

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 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
• 储存条件：
  存储条件：0-10°C，存放在惰性气体中，并且要避免光照、与空气接触以及加热。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: 3,3′′′-Dihexyl-2,2′:5′,2′′:5′′,2′′′-quaterthiophene
Product name
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 132814-91-6
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
Classification according to Regulation (EC) No 1272/2008
Eye irritation (Category 2), H319
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H319 Causes serious eye irritation.
Precautionary statement(s)
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards
Stench.

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SECTION 3: Composition/information on ingredients
Substances
: 5,5′-Bis(3-hexyl-2-thienyl)-2,2′-bithiophene
Synonyms
α,ω-Dihexylquaterthiophene
DH-4T
Formula : C28H34S4
Molecular Weight : 498,83 g/mol
CAS-No. : 132814-91-6
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3,3'''-Dihexyl-2,2':5',2'':5'',2'''-quaterthiophene
CAS-No. 132814-91-6 Eye Irrit. 2; H319 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
3,3'''-Dihexyl-2,2':5',2'':5'',2'''-quaterthiophene
CAS-No. 132814-91-6 Xi, R36 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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, Sulphur 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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. 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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 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
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour Stench.
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 25 - 29 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point > 110 °C
h) Evapouration 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) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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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 sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: 3335
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Aviation regulated solid, n.o.s. (3,3'''-Dihexyl-2,2':5',2'':5'',2'''-quaterthiophene)
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: 9
Packaging group
ADR/RID: - IMDG: - IATA: III
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

制备方法与用途

用途：这种半导电的低聚体（p型）也被用作合成聚(3,3′′′-二烷基-四噻吩)聚合物(PQT)的单体。

反应信息

• 作为反应物：
  描述：

  α,ω-二己基四噻吩 5,5′-双(3-己基-2-噻吩基)-2,2′-联噻吩 在 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以58%的产率得到2,2'''-diiodo-4,4'''-dihexyl-5,2',2'',5''',5',5''-quaterthiophene
  参考文献：
  名称：

  π-堆积的喹啉二甲烷低聚噻吩的制备和表征。从晶体结构和分子轨道计算预测半导体行为和带宽

  摘要：

  已经研究了一系列新的醌二甲烷取代的三联噻吩和四联噻吩低聚物，以与先前研究的醌型低聚噻吩进行比较，后者在薄膜晶体管器件中表现出高迁移率和双极传输行为。每个新的醌型噻吩衍生物在 0.85 到 1.32 V 之间显示出可逆的单电子氧化，在 1.37 到 1.96 V 之间显示出准可逆的单电子第二氧化，以及 -0.05 到 -0.23 V 之间的可逆双电子还原。每种化合物的 UV-vis-NIR 光谱主要由强 (e ≅ 100 000 M-1 cm-1) 低能量 π-π* 跃迁主导，其 λmax 范围在 648 和 790 nm 之间。所有 X 射线晶体结构都表现出非常平面的醌型主链和较短的分子间 π 堆积距离 (3.335−3.492 A)。

  DOI：

  10.1021/ja0484597
• 作为产物：
  描述：

  3-己基噻吩 在 potassium tert-butylate 、 三(邻甲基苯基)磷 、 palladium dichloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 44.63h， 生成 α,ω-二己基四噻吩 5,5′-双(3-己基-2-噻吩基)-2,2′-联噻吩
  参考文献：
  名称：

  通过高效脱羧交叉偶联研究分子掺杂的寡聚噻吩中的整数电荷转移机制。

  摘要：

  使用脱羧交叉偶联反应作为关键转化制备了对称的线性低聚噻吩文库。噻吩羧酸钾盐用作交叉偶联伙伴，而无需助催化剂，碱或添加剂。与现有方法相比，该方法显示出完全的化学选择性，是一种更全面的绿色方法。通过制备具有最多10个噻吩重复单元的谨慎的寡聚噻吩，可以证明这种方法的模块化。对称的低聚噻吩是典型的有机半导体，可以通过光谱评估其分子电掺杂随链长的变化。观察到整数电荷转移的低聚噻吩临界长度为10个噻吩单元，

  DOI：

  10.1002/anie.201914458

文献信息

• [EN] IMPROVED OLIGOTHIOPHENES<br/>[FR] OLIGOTHIOPHÈNES AMÉLIORÉS
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2011137487A1

  公开（公告）日：2011-11-10

  Compounds of Formula (I), wherein T is independently selected from the group consisting of (a). And the variables R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar, L and n are as defined in the specification herein. The compounds are capable of charge transportation and have application in organic photovoltaic devices such as dye sensitised solar cells.

  式（I）的化合物，其中T是从（a）组成的群体中独立选择的。变量R1、R2、R3、R4、R5、R6、R7、R8、R9、Ar、L和n的定义如本说明书中所述。这些化合物能够进行电荷传输，并在有机光伏器件中应用，例如染料敏化太阳能电池。
• Synthesis and Photophysical Properties of Ferrocene−Oligothiophene−Fullerene Triads
  作者：Hiroki Kanato、Kazuo Takimiya、Tetsuo Otsubo、Yoshio Aso、Takumi Nakamura、Yasuyuki Araki、Osamu Ito

  DOI：10.1021/jo049137o

  日期：2004.10.1

  the involvement of intramolecular electron transfer in the photophysical decay process. The additionally conjugated ferrocene evidently contributes to the stabilization of charge separation states, thus promoting intramolecular electron transfer. This is corroborated by the observation that the emission spectra of the nonconjugated triads Fc-tm-nT-C60 are essentially similar to the corresponding dyads

  为了促进以前在低聚噻吩-富勒烯二聚体（nT-C60）中观察到的光诱导电荷分离，我们设计了在低聚噻吩的未取代末端位点上带有强电子给体的二茂铁的附加附件，并合成了两种类型的二茂铁-低聚噻吩-富勒烯三联体，Fc-nT-C60将二茂铁直接连接至低聚噻吩，而Fc-tm-nT-C60在三茂铁与低聚噻吩之间插入三亚甲基间隔基。对于三联体的中央寡聚噻吩，有一系列同源的四噻吩（4T），辛噻吩（8T）和十二聚噻吩（12T））进行系统地检查。Fc-nT-C60的循环伏安图和电子吸收光谱表明二茂铁和低聚噻吩组分之间的共轭。在甲苯中测得的Fc-nT-C60的发射光谱表明，与二重体nT-C60相比，寡噻吩的荧光显着淬灭。用分子内电子转移参与光物理衰变过程来解释这种猝灭。另外共轭的二茂铁显然有助于电荷分离态的稳定，从而促进了分子内电子的转移。通过观察非共轭三联体Fc-tm-nT-C60的发射光谱可以证实这一点与相应的二元组nT-C60基本相似。
• A molecular structure and crystallization correlation study of pyromellitic diimide-based conjugated copolymers
  作者：Ming-Chia Tsai、Ja-Wei Liu、Ping-Tsung Huang

  DOI：10.1002/jccs.201700440

  日期：2018.7

  diimide(PMDI)‐based polymers—poly(pyromellitic diimide‐co‐bithiophene) [poly(PMDI‐BTh)], poly(pyromellitic diimide‐co‐tetrathiophene) [poly(PMDI‐TTh)], and poly(pyromellitic diimide‐co‐benzodithio‐ phene) [poly(PMDI‐BDTTh)]—are synthesized to study the influence of different thiophene‐containing electron‐donating groups on the crystallizability of PMDI‐based conjugated polymers. Computer simulation

  三种基于均苯四甲酸二酰亚胺（PMDI）的聚合物-聚（均苯四甲酸二酰亚胺-共-噻吩）[poly（PMDI-BTh）]，聚（均苯四甲酸二酰亚胺-共-四噻吩）[poly（PMDI-TTh）]和聚（均苯四甲酸）合成了二酰亚胺-共苯并二噻吩[poly（PMDI-BDTTh）]，以研究不同的含噻吩供电子基团对基于PMDI的共轭聚合物结晶性的影响。使用密度泛函理论（DFT）[高斯B3LYP / 6–31 + G（d，p）]进行的计算机模拟表明，聚（PMDI-BDTTh）具有比其他两种共聚物更平坦的分子结构。聚（PMDI-BDTTh）的粉末XRD衍射实验显示，约2θ= 6.0°处有一个衍射峰，但聚（PMDI-BTh）和聚（PMDI-TTh）均未出现衍射峰。尽管PMDI是有利于分子聚集的平面结构，
• 전하 수송성 바니시
  申请人：Nissan Chemical Corporation 닛산 가가쿠 가부시키가이샤(519980958906)

  公开号：KR20160010488A

  公开（公告）日：2016-01-27

  식 (1)로 표시되는 올리고싸이오펜 유도체로 이루어지는 전하 수송성 물질과, 헤테로폴리산으로 이루어지는 도판트 물질과, 유기 용매를 포함하는 전하 수송성 바니시를 사용함으로써 높은 투명성을 갖고, 유기 EL 소자에 적용한 경우에 우수한 휘도 특성과 높은 내구성을 발휘시킬 수 있는 전하 수송성 박막이 얻어진다. (식 중, R〜R는, 서로 독립하여, 수소 원자 등을 나타내고, n〜n은, 서로 독립하여, 자연수를 나타내고, 또한, 4≤n+n+n≤20을 충족시킨다.)

  使用具有标记为(1)的奥利高吡咯烯诱导体组成的带电输运性物质，由杂多酸组成的导电物质，以及含有有机溶剂的带电输运性清漆，通过将其应用于有机EL器件，可获得具有高透明度、优异发光特性和高耐久性的带电输运性薄膜。 (在公式中，R〜R表示相互独立的氢原子等，n〜n表示相互独立的自然数，同时满足4≤n+n+n≤20。)
• Intramolecular Energy Transfer of [60]Fullerene-linked Oligothiophenes
  作者：Takashi Yamashiro、Yoshio Aso、Tetsuo Otsubo、Heqing Tang、Yutaka Harima、Kazuo Yamashita

  DOI：10.1246/cl.1999.443

  日期：1999.5

  [60]Fullerene-linked quarter-, octi-, and duodeci-thiophenes have been synthesized, and their emission spectra demonstrate efficient intramolecular energy transfer from the thiophene moiety to the fullerene, whose rate constant largely depends on the chain length of the oligothiophene moiety.

  合成了与富勒烯相连的四聚、八聚和十二聚噻吩，它们的荧光发射光谱表明，从噻吩部分到富勒烯的高效分子内能量转移，其速率常数很大程度上取决于噻吩低聚物部分的长度。