12,13-Dihydro-12,13-bis(2-octyldodecyl)-3,9-diundecyldithieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-e:2',3'-g][2,1,3]benzothiadiazole-2,10-dicarboxaldehyde
[CAS# 2599837-57-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 12,13-Dihydro-12,13-bis(2-octyldodecyl)-3,9-diundecyldithieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-e:2',3'-g][2,1,3]benzothiadiazole-2,10-dicarboxaldehyde
• Synonyms: 3,27-bis(2-octyldodecyl)-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-decaene-7,23-dicarbaldehyde
• Molecular Formula: C₈₂H₁₃₀N₄O₂S₅
• Molecular Weight: 1364.26
• CAS Registry Number: 2599837-57-5
• SMILES: CCCCCCCCCCCC1=C(SC2=C1SC3=C2N(C4=C3C5=NSN=C5C6=C4N(C7=C6SC8=C7SC(=C8CCCCCCCCCCC)C=O)CC(CCCCCCCC)CCCCCCCCCC)CC(CCCCCCCC)CCCCCCCCCC)C=O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P351-P302+P352

Discovery and Applications

12,13-Dihydro-12,13-bis(2-octyldodecyl)-3,9-diundecyldithieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-e:2',3'-g][2,1,3]benzothiadiazole-2,10-dicarboxaldehyde is a highly specialized organic compound that has drawn attention due to its unique chemical structure and its potential applications in the field of organic electronics, particularly in organic photovoltaics (OPVs). The chemical compound is a derivative of benzothiadiazole, a widely studied unit in the design of organic semiconductors, combined with a series of conjugated thieno-pyrrole moieties that contribute to its optoelectronic properties.

The compound's discovery is part of an ongoing effort to develop more efficient materials for organic solar cells, where improving the donor-acceptor interface is critical for enhancing energy conversion efficiencies. Its structure integrates both electron-donating and electron-accepting functionalities, making it an ideal candidate for use in bulk heterojunctions (BHJs), where the interaction between donor and acceptor materials defines the performance of the device. The incorporation of long alkyl chains, such as 2-octyldodecyl and diundecyl groups, plays a key role in enhancing the solubility and processability of the material, which is crucial for the fabrication of large-area films in OPVs.

One of the most significant features of this compound is its extended π-conjugation system, which enables it to absorb a broader range of the solar spectrum, making it more efficient in converting sunlight into electricity. Additionally, the electron-deficient nature of the benzothiadiazole unit and the incorporation of aldehyde groups at the periphery enhance the material's ability to accept electrons from the donor polymer in an OPV device. These structural characteristics not only improve the photovoltaic performance but also contribute to better charge transport properties and higher stability, which are essential for the long-term operation of organic solar cells.

When incorporated into OPVs, the compound has demonstrated significant improvements in power conversion efficiencies (PCEs). Research indicates that devices made with this material, when paired with suitable donor materials, can achieve PCEs well above 15%, which is competitive with other high-performance non-fullerene acceptors. The combination of good light absorption, efficient charge transfer, and favorable morphology makes this material a strong candidate for next-generation organic solar cells.

Beyond its use in photovoltaics, the compound's high electron mobility and stability also make it a candidate for other optoelectronic applications, such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). The potential for integrating such materials into flexible and lightweight devices further expands their application possibilities in the growing market for flexible electronics.

In conclusion, 12,13-Dihydro-12,13-bis(2-octyldodecyl)-3,9-diundecyldithieno[2'',3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-e:2',3'-g][2,1,3]benzothiadiazole-2,10-dicarboxaldehyde represents a significant advancement in the design of materials for organic photovoltaics and other organic electronic applications. Its unique structure and excellent electronic properties position it as a leading candidate in the development of high-performance, solution-processed organic solar cells.

References

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