4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene
[CAS# 1209012-31-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene
• Synonyms: 5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1,3(10),4(8),6,11,13(17),15-heptaene
• Molecular Formula: C₁₆H₁₀S₂
• Molecular Weight: 266.38
• CAS Registry Number: 1209012-31-6
• SMILES: C1C2=C(C3=CC4=C(C=C31)C5=C(C4)C=CS5)SC=C2

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.780, Calc.^*
• Boiling Point: 467.4±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 178.7±12.2 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene is a fused polycyclic aromatic compound that has attracted considerable attention in organic electronics, particularly in the development of organic semiconductors for applications such as organic photovoltaics (OPVs) and organic field-effect transistors (OFETs). Structurally, it consists of an indacene core fused with two thiophene rings, which imparts desirable electronic properties such as high charge mobility and stability. This compound represents an important building block in the field of organic materials due to its conjugated structure, enabling efficient charge transport and light absorption.

The discovery of 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene can be linked to efforts in improving the performance of organic electronic materials, particularly in the area of organic solar cells. Organic semiconductors have been a focus of intense research due to their potential for producing flexible, lightweight, and cost-effective electronic devices. The inclusion of sulfur-containing heterocycles like thiophene in the molecular structure enhances electron-donating capabilities and contributes to the stabilization of charge carriers, which is crucial for the efficiency of devices like OPVs.

One of the key applications of 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene is in organic photovoltaic devices. These devices convert sunlight into electricity through the photoactive layer, typically made of conjugated polymers or small molecules that can absorb light and generate excitons (bound electron-hole pairs). Due to its extended conjugation and electron-rich sulfur atoms, 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene is utilized as a donor material in bulk heterojunction solar cells. Its molecular structure allows for efficient absorption of sunlight and facilitates charge separation and transport, leading to improved power conversion efficiencies in solar cells.

In addition to solar cells, this compound has been employed in the fabrication of organic field-effect transistors (OFETs), which are used in flexible electronics, sensors, and displays. OFETs require materials with high charge-carrier mobility and good thermal and environmental stability. The rigid and planar structure of 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene, combined with its conjugated backbone, supports efficient charge transport in thin films, making it an ideal candidate for OFET applications. The sulfur atoms in the thiophene rings also enhance the material’s ability to form stable molecular packing in the solid state, which is important for device performance.

Another area where 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene has shown promise is in the development of organic light-emitting diodes (OLEDs). In OLEDs, materials with high charge transport and luminescent properties are crucial for efficient light emission. The combination of its conjugated system and electron-rich thiophene units makes this compound suitable for use in the emissive layers of OLED devices, potentially improving brightness and energy efficiency. OLEDs based on organic semiconductors are being explored for use in next-generation display technologies due to their potential for producing lightweight, flexible, and energy-efficient screens.

The synthesis of 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene involves complex organic reactions, typically starting from simpler aromatic precursors. Its production requires careful control of reaction conditions to ensure the correct fusion of the indacene and thiophene units, which is essential for obtaining the desired electronic properties. Advances in synthetic methods have allowed researchers to fine-tune the properties of this compound by introducing various substituents, enabling the design of materials with specific optical and electronic characteristics.

As organic electronics continue to evolve, 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene and its derivatives are expected to play a key role in improving the performance of devices such as OPVs, OFETs, and OLEDs. Its ability to enhance charge mobility, stability, and light absorption makes it a valuable component in the ongoing development of organic semiconductors.