5,11-Bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene
[CAS# 851817-11-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: 5,11-Bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene
• Synonyms: TES-ADT
• Molecular Formula: C₃₄H₃₈S₂Si₂
• Molecular Weight: 566.97
• CAS Registry Number: 851817-11-3
• SMILES: CC[Si](CC)(CC)C#CC1=C2C=C3C(=CC2=C(C4=C1C=C5C=CSC5=C4)C#C[Si](CC)(CC)CC)C=CS3

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 128-135 °C
• Index of Refraction: 1.642, Calc.^*
• Boiling Point: 654.3±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 349.5±31.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

5,11-Bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene is an organic semiconductor that has garnered attention for its unique chemical structure and potential applications in electronic and optoelectronic devices. This compound consists of an anthradithiophene core, which is functionalized with ethynyl groups, each attached to triethylsilyl groups. The introduction of the triethylsilyl group increases the solubility of the molecule and improves its processing properties, which are crucial for the fabrication of thin-film transistors and organic solar cells.

The discovery of 5,11-bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene emerged from the need to develop new materials for organic electronics with enhanced stability, mobility, and processability. The anthra[2,3-b:6,7-b']dithiophene unit is known for its excellent electronic properties, including high charge carrier mobility and good photophysical characteristics, making it suitable for use in organic semiconductors. By attaching triethylsilyl groups to the ethynyl linkers, researchers aimed to improve the solubility and processability of the material without sacrificing its electronic performance. The compound was synthesized using well-established organic reactions, including Sonogashira coupling to attach the ethynyl groups, followed by functionalization with triethylsilyl groups.

One of the key applications of 5,11-bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene is in organic field-effect transistors (OFETs). Organic semiconductors are often used in thin-film transistors because of their flexibility and potential for low-cost manufacturing. This particular molecule has demonstrated excellent charge transport properties, making it an ideal candidate for use in OFETs. The triethylsilyl functionalization enhances the material’s ability to form thin films and improves its stability, which is critical for the long-term performance of organic electronic devices.

Another major application is in organic solar cells (OSCs). In OSCs, the active layer consists of a blend of donor and acceptor materials. The excellent electron-donating properties of 5,11-bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene make it a promising candidate for the donor material in bulk heterojunction solar cells. The solubility and processability of the compound allow for its incorporation into solution-based processing techniques such as spin-coating and inkjet printing, which are commonly used in the fabrication of flexible and large-area solar cells. Moreover, the molecular structure facilitates good electronic communication between the donor and acceptor phases, improving the overall power conversion efficiency of the device.

The compound also shows promise in other applications, such as organic light-emitting diodes (OLEDs) and organic photodetectors. In OLEDs, materials that exhibit efficient charge transport and emission properties are crucial for high-efficiency devices. The integration of 5,11-bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene in OLED devices could potentially enhance their performance, particularly in applications requiring flexible or transparent displays.

The synthesis of this molecule has been well-studied, and several methods have been proposed to achieve high yields and purity. The key step in its synthesis involves the Sonogashira coupling reaction between an appropriate dihalogenated anthra[2,3-b:6,7-b']dithiophene derivative and the triethylsilyl-ethynyl reagent. This reaction is followed by purification steps, such as column chromatography, to isolate the final product.

In addition to its electronic applications, 5,11-bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene also has potential in the field of organic electronics for flexible and wearable devices. The material's ability to form stable thin films and its high charge mobility could contribute to the development of flexible, lightweight electronics that can be integrated into a variety of applications, such as smart textiles, sensors, and flexible displays.

In summary, 5,11-bis((triethylsilyl)ethynyl)anthra[2,3-b:6,7-b']dithiophene is a promising organic semiconductor with versatile applications in organic electronics, including OFETs, OSCs, OLEDs, and flexible devices. Its unique chemical structure, combined with its excellent electronic properties, makes it a valuable material for the development of next-generation electronic and optoelectronic devices.

References

2005. Organic Field-Effect Transistors from Solution-Deposited Functionalized Acenes with Mobilities as High as 1 cm2/V·s. Journal of the American Chemical Society, 127(14).
DOI: 10.1021/ja042353u