反-1,2-二(2-噻吩基)乙烯 | 13640-78-3

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 反-1,2-二(2-噻吩基)乙烯
• 英文名称: (E)-1,2-bis(2-thienyl)ethene
• 英文别名: trans-1,2-di(2-thienyl)ethylene；(E)-1,2-di(thiophen-2-yl)ethene；(E)-1,2-bis(2-thienyl)ethylene；(E)-1,2-di(2-thienyl)ethene；2-[(E)-2-thiophen-2-ylethenyl]thiophene
• CAS: 13640-78-3
• 化学式: C₁₀H₈S₂
• 分子量: 192.306
• InChiKey: AYBFWHPZXYPJFW-AATRIKPKSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  302.4±11.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 储存条件：
  室温

SDS

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Section I.Chemical Product and Company Identification
Chemical Name trans-1,2-Di(2-thienyl)ethylene
Portland OR
Synonym
3,3'-(1,2-Ethenediyl)bis-thiophene
Chemical Formula
C 10 H 8 S 2
CAS Number
13640-78-3
(International)

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
trans-1,2-Di(2-thienyl)ethylene Min. 98.0 (GC) Not available. Not available.
13640-78-3

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Section III. Hazards Identification
Acute Health Effects
N o specific inform ation is available in our data base regarding the toxic effects of this m aterial for hum ans. H ow ever,
exposure to any chem ical should be kept to a m inim u m . Skin and eye contact m ay result in irritation. M ay be harm ful if
inhaled or ingested. A lw ays follow safe industrial hygiene practices and w ear proper protective equipm ent w hen
handling this com pound. Follow safe industrial hygiene practices and alw ays w ear proper protective equipm ent w hen
handling this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY : Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact
C heck for and rem ove any contact lenses. In case of contact, im m ediately flush eyes w ith plenty of w ater for at least 15
minutes. Get medical attention.
Skin Contact
In case of contact, im m ediately flush skin w ith plenty of w ater. Rem ove contam inated clothing and shoes. W ash
clothing before reuse. Thoroughly clean shoes before reuse. Get medical attention.
Inhalation
If the victim is not breathing, perform m outh-to-m outh resuscitation. Loosen tight clothing such as a collar, tie, belt or
w aistband. If breathing is difficult, oxygen can be adm inistered. Seek m edical attention if respiration problem s do not
improve.
Ingestion
IN D U C E V O M ITIN G by sticking finger in throat. Low er the head so that the vom it w ill not reenter the m outh and throat.
Loosen tight clothing such as a collar, tie, belt or w aistband. If the victim is not breathing, perform m outh-to-m outh
resuscitation. Exam ine the lips and m outh to ascertain w hether the tissues are dam aged, a possible in dication that the
toxic m aterial w as ingested; the absence of such signs, how ever, is not conclusive. SEEK IM M ED IA TE M ED IC A L
ATTENTION in case of ingestion of a radioactive material.

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Section V. Fire and Explosion Data
Flammability Auto-Ignition Not available.
May be combustible at high temperature.
Flammable Limits
Flash Points
Not available.
Not available.
Combustion Products
These products are toxic carbon oxides (CO, CO 2), sulfur oxides (SO 2, SO 3...).
Fire Hazards
Not available.
Explosion Hazards
Risks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
and Instructions
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
Chemi trans-1,2-Di(2-thienyl)ethylene

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Section VI. Accidental Release Measures
Spill Cleanup
U se a shovel to put the m aterial into a convenient w aste disposal container. Finish cleaning the spill by rinsing any
Instructions contam inated surfaces w ith copious am ounts of w ater. C onsult federal, state, and/or local authorities for assistance on
disposal.

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Section VII. Handling and Storage
Handling and Storage
K eep aw ay from heat. M echanical exhaust required. W hen not in use, tightly seal the container and store in a dry, cool
place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls
U se process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recom m ended exposure lim its. If user operations generate dust, fum e or m ist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection
Splash goggles. Lab coat. D ust respirator. Boots. G loves. Suggested protective clothing m ight not be sufficient;
consult a specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits
Not available.

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Section IX. Physical and Chemical Properties
Physical state @ 20°C Solubility
Solid. (Powder.)
Not available.
Specific Gravity Not available.
Molecular Weight Partition Coefficient
192.3 Not available.
Boiling Point Vapor Pressure
Not available. Not applicable.
Melting Point Vapor Density
133°C (271.4°F) Not available.
Refractive Index Volatility
Not available. Not available.
Critical Temperature Odor
Not available. Not available.
Viscosity Taste
Not available. Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability
Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
RTECS Number
Not available.
Routes of Exposure
Eye Contact. Ingestion. inhalation.
Toxicity Data
Not available.
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY : Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects
N o specific inform ation is available in our data base regarding the toxic effects of this m aterial for hum ans. H ow ever,
exposure to any chem ical should be kept to a m inim u m . Skin and eye contact m ay result in irritation. M ay be harm ful if
inhaled or ingested. A lw ays follow safe industrial hygiene practices and w ear proper protective equipm ent w hen
handling this com pound. Follow safe industrial hygiene practices and alw ays w ear proper protective equipm ent w hen
handling this compound.
Continued on Next Page
trans-1,2-Di(2-thienyl)ethylene

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Section XII. Ecological Information
Ecotoxicity
Not available.
Environmental Fate
Not available.

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Section XIII. Disposal Considerations
Waste Disposal Recycle to process, if possible. C onsult your local regional authorities. You m ay be able to dissove or m ix m aterial w ith a
com bustible solvent and burn in a chem ical incinerator equipped w ith an afterburner and scrubber system . O bserve all
federal, state and locl regulations when disposing of the substance.

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Section XIV. Transport Information
DOT Classification
Not a DOT controlled material (United States).
PIN Number
Not applicable.
Proper Shipping Name
Not applicable.
Packing Group (PG)
Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory
T h is p r o d u c t is NOT o n t h e E P A T o x ic S u b s t a n c e s C o n t r o l A c t (T S C A ) in v e n t o r y . T h e f o llo w in g n o t ic e s a r e r e q u ir e d b y 4 0
(EPA) CFR 720.36 (C) for those products not on the inventory list:
(i) These products are supplied solely for use in research and developm ent by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determ ined. A ny inform ation that is or becom es available w ill
be supplied on an MSDS sheet.
WHMIS Classification
Not available.
(Canada)
EINECS Number (EEC)
Not available.
EEC Risk Statements
Not available.
Japanese Regulatory Data Not available.

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Section XVI.
Version 1.0
Validated on 3/16/2001.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

溶解性（溶于）对二甲苯：几乎无色

反应信息

• 作为反应物：
  描述：

  反-1,2-二(2-噻吩基)乙烯 在 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以85%的产率得到(E)-1,2-bis(5-iodothiophen-2-yl)ethylene
  参考文献：
  名称：

  基于具有不饱和键的联噻吩的共轭寡聚噻吩衍生物，作为溶液处理的本体异质结有机太阳能电池的构建基块

  摘要：

  已经开发了一种新的ATVTA结构，该结构在1,2-二（2-噻吩基）-乙烯（TVT）上使用硬碳-碳三键（A）。低聚噻吩衍生物S-01与TVT单元，S-02与5,5'-二乙炔基-2,2'-二噻吩基（AT2）单元和S-03与ATVTA合成在了系统的研究，以比较它们的作用。由于TVT单元具有更好的π共轭扩展性，因此S-01在其中具有最大的红移吸收曲线，而S-02具有最深的HOMO水平。同时的HOMO能级S-03通过电子伏特相对0.02是下移到的S-01，炔烃链接可以有效地降低HOMO的水平。通过更换的终端单元S-03具有更强的电子受体，S-04和S-05表现出更宽的吸收曲线和HOMO能级比那些低S-03。制造了基于这些分子的有机太阳能电池，并且基于S-03：PC 60 BM（1：1，w / w）的设备提供了0.96 V的最高V oc值和2.19％的功率转换效率（PCE）。

  DOI：

  10.1002/asia.201601281
• 作为产物：
  描述：

  2-噻吩乙酸 在 乙酸酐 、 铜 、 三乙胺 作用下， 以 喹啉 为溶剂， 反应 1.75h， 生成 反-1,2-二(2-噻吩基)乙烯
  参考文献：
  名称：

  新型脒基-苯并咪唑基噻吩：合成和光化学合成

  摘要：

  新型脒基-苯并咪唑基取代的双-1,2-（2-噻吩基）乙烯（4、5 和 6）和苯并[1,2-b:4,3-b']二噻吩（8、9 和 10） ) 是通过脒基取代的邻苯二胺与相应的二醛 (3 和 7) 缩合制备的。所有制备的脒基-苯并咪唑基取代的化合物都特别令人感兴趣，因为它们可以在抗癌治疗中作为 DNA 的嵌入剂或凹槽结合剂。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:218–222, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10126

  DOI：

  10.1002/hc.10126

文献信息

• Semiconductor materials prepared from dithienylvinylene copolymers
  申请人：Mishra Ashok Kumar

  公开号：US09221944B2

  公开（公告）日：2015-12-29

  Disclosed are new semiconductor materials prepared from dithienylvinylene copolymers with aromatic or heteroaromatic π-conjugated systems. Such copolymers, with little or no post-deposition heat treatment, can exhibit high charge carrier mobility and/or good current modulation characteristics. In addition, the polymers of the present teachings can possess certain processing advantages such as improved solution-processability and low annealing temperature.

  披露了由含芳香或杂芳香π-共轭系统的二噁唑基乙烯共聚物制备的新半导体材料。这种共聚物在几乎没有或没有后沉积热处理的情况下，可以表现出高载流子迁移率和/或良好的电流调制特性。此外，根据本教导的聚合物可以具有某些加工优势，如改善的溶液加工性能和低退火温度。
• Towards High‐Performance Resistive Switching Behavior through Embedding a D‐A System into 2D Imine‐Linked Covalent Organic Frameworks
  作者：Chenyu Li、Dong Li、Weifeng Zhang、Hao Li、Gui Yu

  DOI：10.1002/anie.202112924

  日期：2021.12.20

  Two D-A-type covalent organic frameworks have been designed and prepared following a novel strategy for the construction of endurable and reliable memory devices. The state-of-the-art memristor-based COF-TT-BT thin film showed typical rewritable resistive switching behavior, a high ON/OFF current ratio (ca. 105), good endurance of 319 cycles, and a long retention time of 3.3×104 s.

  遵循用于构建耐用且可靠的存储设备的新策略，已经设计和制备了两种 DA 型共价有机框架。最先进的基于忆阻器的COF-TT-BT薄膜表现出典型的可重写电阻开关行为、高 ON/OFF 电流比（约 10 5）、319 次循环的良好耐久性和长保留时间3.3×10 4 秒。
• Synthesis of novel conjugated oligomers for second-order nonlinear optics: incorporation of a central spacer as a conjugation modulator
  作者：Jian Xin Zhang、Philippe Dubois、Robert Jérôme

  DOI：10.1039/a606547c

  日期：——

  A new series of second-order nonlinear optical chromophores has been synthesized that consists of a conjugated segment end-capped with an electron acceptor and an electron donor, respectively, and a central spacer intended to modulate the electro-optical effect. Conjugated chains have been tailored with trans-vinylene-1,5-thienylene as the building unit and N,N-dimethylamino and nitro groups as the donor–acceptor pair. Four spacers have been incorporated into the central part of the conjugated oligomers, which range from saturated to totally unsaturated functions, i.e. from methylene to vinylene units. The general strategy relies upon two consecutive Wittig or Wittig–Horner reactions between the spacer precursor and an aromatic phosphonium or phosphonate bearing the strong electron donor and the acceptor, respectively. Two synthetic pathways have been studied. The first procedure is based on the use of a symmetric precursor for the spacer. However, a reaction byproduct is formed, which must be removed and decreases the reaction efficiency. The second approach requires an asymmetric precursor for the spacer, the synthesis of which is a multistep process. In order to evaluate the effect of the spacer, a completely conjugated oligomer has been prepared by the one-step coupling of two conjugated segments end-functionalized by the electron donor and the acceptor, respectively.

  一种新的二阶非线性光学染料系列已被合成，该系列由一个共轭段组成，两端分别封端为电子受体和电子给体，并包含一个中心间隔器，旨在调节电光效应。共轭链使用反式乙烯-1,5-噻吩单元作为构建单元，N,N-二甲基氨基和硝基作为给体–受体对。四种间隔器被引入到共轭 oligomer 的中央部分，这些间隔器从饱和功能到完全不饱和功能，即从亚甲基到乙烯基单元。一般策略依赖于间隔器前体与带有强电子给体和受体的芳香族膦盐或膦酸酯之间的两次连续 Wittig 或 Wittig–Horner 反应。研究了两条合成路径。第一种程序基于使用对称前体作为间隔器。然而，会形成一个反应副产物，必须去除，这降低了反应效率。第二种方法需要不对称的间隔器前体，其合成是一个多步过程。为了评估间隔器的影响，通过将两个分别被电子给体和受体功能化的共轭段进行一步耦合，制备了一个完全共轭的 oligomer。
• ORGANIC SEMICONDUCTING COMPOUNDS AND RELATED OPTOELECTRONIC DEVICES
  申请人：Polyera Corporation

  公开号：US20170104160A1

  公开（公告）日：2017-04-13

  The present teachings relate to new organic semiconducting compounds and their use as active materials in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The present compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The present compounds can have good solubility in common solvents enabling device fabrication via solution processes.

  本教学涉及新的有机半导体化合物及其在有机和混合光学、光电子和/或电子器件中作为活性材料的用途，如光伏电池、发光二极管、发光晶体管和场效应晶体管。这些化合物可以提供改进的器件性能，例如通过光电转换效率、填充因子、开路电压、场效应迁移率、开/关电流比以及在光伏电池或晶体管中使用时的空气稳定性等指标来衡量。这些化合物在常见溶剂中具有良好的溶解性，可以通过溶液工艺进行器件制备。
• Design and Synthesis of Push−Pull Chromophores for Second-Order Nonlinear Optics Derived from Rigidified Thiophene-Based π-Conjugating Spacers
  作者：Jean-Manuel Raimundo、Philippe Blanchard、Nuria Gallego-Planas、Nicolas Mercier、Isabelle Ledoux-Rak、Rolland Hierle、Jean Roncali

  DOI：10.1021/jo010713f

  日期：2002.1.1

  Two series of push-pull chromophores built around thiophene-based pi-conjugating spacers rigidified either by covalent bonds or by noncovalent intramolecular interactions have been synthesized and characterized by UV-vis spectroscopy, electric field induced second harmonic generation (EFISH) and differential scanning calorimetry. Comparison of the linear and second-order nonlinear optical properties

  合成了两个系列的推挽生色团，它们围绕通过共价键或通过非共价分子内相互作用而硬化的基于噻吩的pi共轭间隔基构建，并通过紫外可见光谱，电场诱导的二次谐波产生（EFISH）和差示扫描量热法进行了表征。基于共价桥联二噻吩基乙烯（DTE）间隔基的发色团与基于开链DTE的类似物的生色团的线性和二阶非线性光学性质的比较表明，间隔基的刚性共同导致吸收最大值的显着红移分子二次超极化率（mu beta）大大提高，达到了迄今为​​止报道的最高值。NLO-phores的第二系列是从2,2' -双（3,4-乙撑二氧噻吩）（BEDOT）π共轭间隔基。如X射线和UV-vis数据所示，在这种情况下，间隔物的刚性源自硫和氧原子之间的非共价分子内相互作用。再次，与基于未取代的联噻吩间隔基的母体化合物的比较揭示了最大吸收的显着红移和μβ的大大增强。为了区分乙二氧基的电子和几何效应的贡献，已经合成了基于3，4-乙二氧基噻吩（ED