5,12-Dibromo-2,9-bis(2-octyldodecyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone
[CAS# 1100243-37-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 5,12-Dibromo-2,9-bis(2-octyldodecyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone
• Synonyms: 11,22-dibromo-7,18-bis(2-octyldodecyl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• Molecular Formula: C₆₄H₈₈Br₂N₂O₄
• Molecular Weight: 1109.20
• CAS Registry Number: 1100243-37-5
• SMILES: CCCCCCCCCCC(CCCCCCCC)CN1C(=O)C2=C3C(=CC(=C4C3=C(C=C2)C5=C(C=C6C7=C(C=CC4=C57)C(=O)N(C6=O)CC(CCCCCCCC)CCCCCCCCCC)Br)Br)C1=O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.594, Calc.^*
• Boiling Point: 996.8±65.0 ºC (760 mmHg), Calc.^*
• Flash Point: 556.6±34.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

5,12-Dibromo-2,9-bis(2-octyldodecyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone, often abbreviated for simplicity in the scientific community, is a highly specialized chemical compound that belongs to the class of perylene diimides (PDIs). This compound is noted for its distinctively tailored molecular structure, characterized by the dibromo substitution at positions 5 and 12 of the anthraquinone core and the incorporation of long, branched alkyl chains. These structural features impart unique electronic and solubility properties, making it a valuable material in advanced technological applications.

The compound's discovery was part of an effort to design functional organic semiconductors for use in electronic devices. Researchers synthesized it via bromination reactions involving perylene diimide precursors, coupled with alkylation steps to introduce the octyldodecyl chains. The resulting material exhibited enhanced solubility in organic solvents and the ability to form uniform thin films, both of which are essential for its application in solution-processable devices.

5,12-Dibromo-2,9-bis(2-octyldodecyl)anthradiisoquinoline tetraone has found its primary application in the field of organic electronics, particularly in organic photovoltaics (OPVs) and organic field-effect transistors (OFETs). The bromine atoms in the molecule facilitate further functionalization through cross-coupling reactions, allowing researchers to tailor its electronic properties for specific device applications. The compound’s conjugated core and substituents contribute to high electron mobility, excellent photostability, and the ability to form well-ordered structures in thin films.

In OPVs, this compound is often used as an electron acceptor material. When paired with suitable donor materials, it enables efficient charge separation and transport within the active layer of the solar cell. Studies have demonstrated that devices incorporating this molecule achieve high power conversion efficiencies due to its strong light absorption in the visible region and efficient energy transfer characteristics.

In addition to photovoltaics, the compound is also used in n-type OFETs, where its robust electron-transporting capabilities and thermal stability make it a reliable component in circuits. Its ability to self-assemble into well-organized nanostructures further enhances its performance in these applications. Moreover, the long alkyl chains improve film-forming properties and prevent aggregation, ensuring consistent performance across large-area devices.

Beyond organic electronics, the compound has potential in developing sensors and imaging systems due to its strong fluorescence and photochemical stability. Researchers are investigating its use in optoelectronic sensors, where its tailored structure allows selective interaction with target analytes, leading to changes in its optical or electronic properties.

Despite its promising applications, challenges remain in scaling up its production and further optimizing its properties for commercial use. The synthesis involves multiple steps that require precise conditions and high-purity reagents, making it costly and time-intensive. Efforts are underway to streamline synthetic routes and develop scalable processes to meet the demands of industrial applications.

In summary, 5,12-Dibromo-2,9-bis(2-octyldodecyl)anthradiisoquinoline tetraone represents a remarkable achievement in the field of functional organic materials. Its tailored structure, combining electronic functionality with processability, underscores its importance in advancing organic electronics and related technologies.