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3,4-Dimethoxythiophene (DMOT) is a monomer and precursor that can be synthesized through a closed-loop reaction of 2,3-dimethoxy-1,3-butadiene with sulfur dichloride in a hexane medium. It is a colorless or slightly yellow liquid that exhibits volatility at room temperature. It is an organic compound, commonly in the form of a liquid. The molecular formula is C6H8O2S, CAS 51792-34-8, and the relative molecular weight is 144.19 g/mol. Under open flames or high temperature conditions, it can burn and release toxic gases and smoke. It is an oligothiophene mainly used for the development of electroactive materials in organic electronic applications. DMOT can undergo ester exchange reaction to form 3,4-ethylenedioxythiophene (EDOT). It can further polymerize to generate PEDOT, which can be used as a conductive polymer in π conjugated systems. It can polymerize to form poly (dimethoxythiophene), which is expected to be used for electrochemical doping to manufacture energy storage devices. Synthesis of N2S2-N4 porphyrin binary components for studying photoinduced energy transfer.
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C.F |
C6H8O2S |
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E.M |
144 |
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M.W |
144 |
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m/z |
144 (100.0%), 145 (6.5%), 146 (4.5%) |
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E.A |
C, 49.98; H, 5.59; O, 22.19; S, 22.23 |
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3,4-Dimethoxythiophene has a wide range of applications in chemical sensors. A chemical sensor is a device that can detect and measure specific chemical substances, and DMOT plays an important role in the construction and reaction mechanism of the sensor.
1. Metal ion sensor:DMOT can undergo coordination reactions with different metal ions to form stable complexes, making it suitable for constructing metal ion sensors. By detecting optical, electrochemical, or fluorescence changes caused by binding with target metal ions, high sensitivity and selectivity can be achieved for metal ion detection. For example, DMOT can be modified to detect mercury and copper ions.
2. pH sensor:DMOT undergoes strong redox reactions in acid-base media and can be used to construct pH sensors. When the pH of the environment changes, the electrochemical properties of DMOT will change, which can be monitored by measuring parameters such as current, potential, or conductivity.
3. Gas sensor:By modifying DMOT on the electrode surface, a gas sensor can be constructed. The presence of DMOT in a specific gas can cause changes in the electrochemical signal, thereby achieving the detection of that gas. For example, DMOT can be used to detect oxygen concentration in the air.
4. Biosensors:By functionalizing DMOT with biological molecules such as antibodies and enzymes, a biosensor can be constructed. This type of biosensor can be used to detect the presence or activity of biological molecules. When the target biomolecule interacts specifically with the modified DMOT, it can cause changes in optical, electrochemical, or fluorescence signals, thereby achieving high sensitivity and selectivity in the detection of biomolecules.
5. Oxidation-reduction sensor:Due to the redox reaction properties of DMOT, it can be used to construct redox sensors. This sensor can monitor the occurrence of redox reactions by measuring the current or charge transfer of thiophene under potential changes. These sensors are widely used in fields such as environmental monitoring and food safety.
When DMOT is used as a material for chemical sensors, it is usually necessary to cooperate with other auxiliary materials (such as carriers, electrolytes, electrodes, etc.) to improve the performance and stability of the sensor. In addition, specific applications may vary depending on the type of sensor, target substance, and measurement conditions.
6. Organic solar cells:DMOT can be used as a conjugated polymer monomer in organic solar cells. By polymerizing DMOT or copolymerizing with other conjugated monomers, conductive polymer materials with good photovoltaic properties can be formed. This conductive polymer has a wide light absorption range and high carrier mobility, and can be used as a photoelectric conversion material in solar cells.
7. Field effect transistor:DMOT can be polymerized into conductive polymer films in organic field-effect transistors (OFETs). These conductive polymer films can serve as active layers for OFET to achieve charge transfer and amplification functions. Its excellent conductivity and adjustable energy level structure make it an ideal material for preparing high-performance OFET.
8. Supercapacitors:DMOT is copolymerized with other conductive polymers or active materials to form composite materials, which can be used to prepare electrode materials for supercapacitors. Due to its high conductivity and good ion conductivity, this conductive polymer composite material exhibits excellent capacitive performance and cyclic stability in the field of energy storage.
Method 1 for the synthesis of 3,4-dimethoxythiophene:
Add a small amount of 6 mL (67 mmol) of 232 butanediol, 9 mL (205 mmol) of n-hexane (polymerization inhibitor), and a small amount of hexadecane trimethyl bromide (catalyst) to the bottle in sequence. 22 mL (83 mmol) of orthoformate methyl acetate was added in batches from a constant pressure drip funnel, and then stirred and refluxed for 8 hours. After the reaction, place the mixture at 0-5C and slowly add 13 mL of 014 mol/L sodium acetate (n-hexane as solvent) and 15 m of 50% sulfur dichloride solution (n-hexane as solvent). After 015 hours, recover to room temperature and react for 10 hours under N protection, and filter to obtain the crude product. After vacuum distillation, a residue of 62~64C/66616 Pa was collected to obtain 312 mL of the target product, 342 dimethyl phene, in a yield of 60% HNMR (CDC3)&: 3186 (s, 6H, 220CH); 6118 (s, 2H, exposed to phene ring gas). IR (KBr), v, cm-1:3 117 (C-H exposed phene ring); 3 000~2825 (C-HO-CH); 1 569,1 500 (C-C); 14491 410 (C-H deformation). UV2Vis (CHC3) x, nm: 251 (7 750) 222 (5 030)
Method 2:
(1) Dissolve sodium 2,5-dicarboxylic acid methyl ester 3,4-thiophenediol in N, N-dimethylformamide, add alkylation reagent, heat and reflux to obtain crude 2,5-dicarboxylic acid methyl ester DMOT;
(2) Add sodium hydroxide solution to the crude product of 3,4-dimethoxy-2,5-dicarboxylic acid methyl ester thiophene, and heat the reaction to obtain the crude product of 3,4-methoxy-2,5-thiophene dicarboxylic acid;
(3) Add a decarboxylation catalyst to a mixture of 3,4-methoxy-2,5-thiophene dicarboxylic acid crude and ethylene glycol solvent, heat decarboxylation, and distill to obtain DMOT finished product. The ethylene glycol solvent can be reused. The process route of this method is environmentally friendly, the production raw materials are easy to obtain, the post-treatment method is simple, and the product yield of the present invention process is high, the cost is low, and the quality is stable.
The molecular structure characteristics of DMOT are as follows:
1. Molecular formula: C6H8O2S
-C represents carbon element, H represents hydrogen element, O represents oxygen element, and S represents sulfur element.
-The number in the molecular formula represents the number of atoms, indicating that the molecule contains 6 carbon atoms, 8 hydrogen atoms, 2 oxygen atoms, and 1 sulfur atom.
2. Structural diagram:
-The structure of DMOT consists of a thiophene ring and two methoxy groups.
-The thiophene ring is composed of four carbon atoms and one sulfur atom, forming a five membered ring.
-Carbon sulfur bonds are formed between sulfur atoms and adjacent carbon atoms by sharing electron pairs.
-The third and fourth positions on the thiophene ring are respectively connected to a methoxy group, that is, a carbon atom is connected to an oxygen atom through a single bond.
3. Molecular structure:
-The structure of DMOT can be further described as a flat circular molecule.
-All atoms are located on the same plane, giving molecules the characteristics of conjugated systems.
-Conjugated systems refer to structures with continuous π electron clouds, which contribute to the stability and conductivity of molecules.
4. Atomic connection:
-Two carbon sulfur bonds are formed between sulfur atoms and adjacent two carbon atoms, with higher strength.
-Carbon atoms are connected to oxygen atoms through carbon oxygen bonds, which are a strong polar covalent bond.
5. Molecular properties:
-DMOT is an organic compound and therefore has typical characteristics of organic molecules.
-Its flat circular structure allows the molecule to form a stacking structure in solution, thereby affecting its physical and chemical properties.
-The methoxy group of DMOT provides molecular electrophilicity and may participate in reactions or interact with other substances.
3,4-Dimethoxythiophene is an organic compound containing a thiophene ring and a methoxy group. Its molecular structure consists of a flat thiophene ring and two methoxy groups connected at positions 3 and 4. This structure allows molecules to have a conjugated system, which helps improve their conductivity and stability. DMOT forms a stacking structure in solution and exhibits some typical organic molecular characteristics.
3,4-Dimethoxythiophene (DMOT) is an important thiophene derivative with the chemical formula C6H8O2S, in which the 3,4 positions of the thiophene ring are replaced by methoxy groups. As a key building block of organic electronic materials, DMOT has significant application value in fields such as conductive polymers, organic light-emitting diodes (OLEDs), and organic solar cells.
The research on thiophene compounds began in the late 19th century. In 1883, German chemist Victor Meyer first isolated thiophene from coal tar and determined its basic structure. In the following decades, chemists began to systematically study the synthesis and properties of thiophene and its derivatives.
The synthesis history of 3,4-dimethoxythiophene is relatively late. In 1965, American chemist Frank M. Dean first reported the laboratory synthesis of 3,4-dimethoxythiophene while studying the electrophilic substitution reaction of thiophene. Dean's method is to first sulfonate thiophene with fuming sulfuric acid, then react with iodomethane under alkaline conditions, and finally obtain the target product through hydrolysis. Although this route is cumbersome and has a low yield (about 25%), it provides an important reference for subsequent research.
In the early 1970s, with the development of organic synthesis methodology, the synthesis route of DMOT was improved.
In 1972, French chemist Jean Pierre Sauvage (later awarded the 2016 Nobel Prize in Chemistry for molecular machine research) developed a new method for synthesizing DMOT through nucleophilic substitution reaction of 3,4-dibromothiophene with sodium methoxide, increasing the yield to around 50%. The research during this period mainly focused on the basic chemical properties of DMOT, and the understanding of its potential applications is not yet sufficient.
The accurate characterization of DMOT molecular structure has undergone a gradual improvement process. In 1975, the Hans Christoph Wolf team at the Max Planck Institute in Germany first determined the crystal structure of DMOT through X-ray single crystal diffraction, revealing its planar molecular configuration and intermolecular stacking mode. This work laid the foundation for understanding the solid-state properties of DMOT.
In the 1980s, with the development of quantum chemistry computational methods, people gained a deeper understanding of the electronic structure of DMOT. In 1983, the research team of Japanese theoretical chemist Kenichi Fukui (winner of the 1981 Nobel Prize in Chemistry) applied the frontier orbital theory to analyze the electron distribution of DMOT and found that the electron donating effect of methoxy significantly increased the electron density of the thiophene ring. This characteristic was later proven to be crucial for its application in conductive polymers.
The advancement of nuclear magnetic resonance technology has also provided new tools for DMOT research. In 1987, the high-resolution NMR technique developed by American chemist Richard R. Ernst (1991 Nobel laureate in Chemistry) was the first to clearly observe the chemical shift differences of protons at different positions in DMOT, providing a standard reference for the structural identification of subsequent derivatives.
The 1990s was a period of great development for the synthesis method of DMOT. In 1992, the team of American chemist Alan G. MacDiarmid (winner of the 2000 Nobel Prize in Chemistry) developed a new process for the one-step preparation of DMOT from 3,4-dihydroxythiophene via Williamson ether synthesis reaction, with a yield of up to 85%. This method became the foundation of later industrial production due to its high efficiency and scalability.
The introduction of catalytic technology further enhances the atomic economy of DMOT synthesis. In 1998, Japanese chemist Ryoji Noyori (winner of the 2001 Nobel Prize in Chemistry) reported the direct coupling reaction of 3,4-dihalothiophene with methanol catalyzed by copper, which avoids the use of strong bases and is more suitable for large-scale production.
In 2005, BASF, a German company, established its first industrial production line for DMOT based on this catalytic system, with an annual capacity of 100 tons.
In recent years, green synthesis has become a research hotspot in the preparation of DMOT. In 2015, a team of Chinese scientist Academician Zhang Suojiang developed an electrochemical synthesis method in ionic liquid medium, achieving clean production of DMOT. In 2018, researchers from the Massachusetts Institute of Technology reported a new strategy for photocatalytic synthesis of DMOT, further reducing energy consumption and waste generation.
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