2,2'-(((12,13-Bis(2-butyloctyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile
[CAS# 2414918-25-3]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 2,2'-(((12,13-Bis(2-butyloctyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile
• Synonyms: 2-[(2Z)-2-[[3,27-bis(2-butyloctyl)-23-[(Z)-[5,6-dichloro-1-(dicyanomethylidene)-3-oxoinden-2-ylidene]methyl]-8,22-di(undecyl)-6,10,15,20,24-pentathia-3,14,16,27-tetrazaoctacyclo[16.9.0.02,12.04,11.05,9.013,17.019,26.021,25]heptacosa-1(18),2(12),4(11),5(9),7,13,16,19(26),21(25),22-decaen-7-yl]methylidene]-5,6-dichloro-3-oxoinden-1-ylidene]propanedinitrile
• Molecular Formula: C₉₀H₁₀₂Cl₄N₈O₂S₅
• Molecular Weight: 1629.96
• CAS Registry Number: 2414918-25-3
• SMILES: CCCCCCCCCCCC1=C(SC2=C1SC3=C2N(C4=C3C5=NSN=C5C6=C4N(C7=C6SC8=C7SC(=C8CCCCCCCCCCC)/C=C/9\C(=O)C1=CC(=C(C=C1C9=C(C#N)C#N)Cl)Cl)CC(CCCCCC)CCCC)CC(CCCCCC)CCCC)/C=C/1\C(=O)C2=CC(=C(C=C2C1=C(C#N)C#N)Cl)Cl

Discovory and Applicatios

2,2'-(((12,13-Bis(2-butyloctyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile is a complex and innovative molecular compound that has been engineered for use in advanced optoelectronic devices, particularly in organic photovoltaics (OPVs). This compound is a highly functionalized non-fullerene acceptor (NFA) material designed to enhance the performance and stability of organic solar cells, an area of growing interest due to the demand for sustainable, flexible, and low-cost energy solutions.

The discovery and synthesis of this compound represent a breakthrough in the development of organic semiconductors with improved efficiency and processability. Its structure incorporates multiple fused aromatic rings and functional groups, including thiadiazole, pyrrole, thieno[3,2-b]indole, and malonitrile units, which contribute to its strong light absorption, excellent charge transport properties, and enhanced electron-accepting capabilities. The addition of bulky side chains, such as butyloctyl and undecyl groups, improves its solubility and film-forming ability, making it suitable for solution-based processing techniques like spin-coating, which are commonly used in large-scale production of organic solar cells.

The unique molecular structure of 2,2'-(((12,13-Bis(2-butyloctyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile allows it to exhibit superior optoelectronic properties compared to conventional fullerene-based acceptors. The malonitrile group, in particular, serves as an electron-withdrawing unit, which boosts the electron affinity and makes the material highly effective in accepting electrons from donor polymers. The compound’s ability to absorb light efficiently across a broad range of the visible and near-infrared spectrum is crucial for achieving high power conversion efficiencies (PCEs) in organic solar cells.

This compound’s integration into organic solar cells has demonstrated significant potential to overcome some of the limitations faced by traditional organic photovoltaics. While fullerene acceptors are still widely used, they have drawbacks such as poor light absorption and limited stability. The incorporation of non-fullerene acceptors like this compound has been shown to enhance not only the efficiency of charge transfer and transport but also the overall stability and operational lifetime of organic solar cells.

When combined with suitable donor polymers, this NFA material has been shown to contribute to organic solar cells with power conversion efficiencies (PCEs) exceeding 15%, making it highly competitive with current state-of-the-art devices. Furthermore, its enhanced thermal and photostability ensures that devices incorporating this material will perform reliably under various environmental conditions, a critical factor for the commercialization of organic solar technology.

In addition to its application in organic photovoltaics, this material’s unique electronic structure opens up possibilities for its use in other optoelectronic applications, such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). The ability to fine-tune the electronic properties of this material through molecular design makes it an attractive candidate for a wide range of electronic applications.

In conclusion, 2,2'-(((12,13-Bis(2-butyloctyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]thieno[3,2-b]indole-2,10-diyl)bis(methaneylylidene))bis(5,6-dichloro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile is a promising non-fullerene acceptor material with significant potential in organic electronics. Its innovative molecular design offers a pathway to highly efficient, stable, and scalable organic solar cells, and it may play a key role in the future of renewable energy technologies.