4,9-Bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
[CAS# 1178586-27-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 4,9-Bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
• Synonyms: 2,9-bis(5-bromothiophen-2-yl)-6,13-bis(2-octyldodecyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• Molecular Formula: C₆₂H₈₈Br₂N₂O₄S₂
• Molecular Weight: 1149.31
• CAS Registry Number: 1178586-27-0
• SMILES: CCCCCCCCCCC(CCCCCCCC)CN1C(=O)C2=CC(=C3C4=C(C=C(C(=C24)C1=O)C5=CC=C(S5)Br)C(=O)N(C3=O)CC(CCCCCCCC)CCCCCCCCCC)C6=CC=C(S6)Br

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.566, Calc.^*
• Boiling Point: 1008.8±65.0 ºC (760 mmHg), Calc.^*
• Flash Point: 563.9±34.3 ºC, Calc.^*

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

Discovory and Applicatios

4,9-Bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone is a highly specialized molecule that belongs to a class of conjugated organic compounds. Known for its unique combination of a conjugated aromatic core and extended branched alkyl chains, this compound has garnered significant attention for its potential applications in organic electronics, especially in organic photovoltaics (OPVs) and organic light-emitting diodes (OLEDs).

The compound was first synthesized as part of efforts to develop semiconducting materials with enhanced solubility, film-forming properties, and tunable optoelectronic characteristics. The incorporation of bromo-thienyl groups and alkyl substituents into the benzo[lmn][3,8]phenanthroline-tetrone framework was designed to improve its π-π stacking interactions, broaden its light absorption range, and facilitate chemical modifications for tailored electronic properties.

In the synthesis of this compound, bromination of thienyl-functionalized precursors and subsequent coupling reactions play a pivotal role. The alkyl chains, specifically the octyldodecyl groups, are introduced to increase solubility in organic solvents, a critical property for solution-processable devices. This design enables the compound to be applied in thin-film deposition techniques such as spin-coating or inkjet printing, making it suitable for scalable manufacturing.

Applications of 4,9-bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone are primarily concentrated in the field of organic electronics. In OPVs, it functions as an electron-acceptor material. Its extended conjugated core provides strong absorption in the visible spectrum, while its structural rigidity and planarity enhance charge mobility. Paired with donor polymers, it enables efficient charge separation and transport, critical for achieving high power conversion efficiencies.

The compound also shows promise in OLEDs, where its strong emission characteristics can be utilized for light generation. Its tunable electronic properties allow researchers to optimize the emission color and improve device efficiency. Additionally, the bromo substituents provide handles for further functionalization, enabling the synthesis of derivatives with customized properties for specific applications.

Beyond its role in organic electronics, this molecule is being explored in the design of sensing and imaging systems due to its photophysical properties. It exhibits strong fluorescence and good stability under various conditions, making it a candidate for advanced optical sensing platforms.

Challenges in its application include the complexity of its synthesis and the need for optimization in device fabrication processes. While the current methods produce high-purity material, scaling up the production in a cost-effective manner remains an area of active research. Additionally, the compound’s stability and performance under long-term operation are being investigated to ensure its viability for commercial applications.

In summary, 4,9-bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone represents a significant advancement in the development of functional organic semiconductors. Its carefully engineered structure combines optical and electronic properties with processability, making it a promising material for next-generation optoelectronic devices.