5,10,15,20-Tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene
[CAS# 175606-05-0]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: 5,10,15,20-Tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene
• Synonyms: DBP; 7,14,25,32-Tetraphenylundecacyclo[21.13.2.22,5.03,19.04,16.06,15.08,13.020,37.024,33.026,31.034,38]tetraconta-1,3,5,7,9,11,13,15,17,19,21,23,25,27,29,31,33,35,37,39-icosaene
• Molecular Formula: C₆₄H₃₆
• Molecular Weight: 804.97
• CAS Registry Number: 175606-05-0
• SMILES: C1=CC=C(C=C1)C2=C3C=CC=CC3=C(C4=C5C=CC6=C7C=CC8=C9C(=C1C=CC=CC1=C(C9=C1C8=C7C(=C3C6=C5C(=C24)C=C3)C=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1

Properties

• Density: 1.3±0.0 g/cm³, Calc.^*
• Melting point: >400 ºC

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

Discovory and Applicatios

5,10,15,20-Tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene is a polycyclic aromatic compound that has attracted significant attention in the field of advanced materials due to its unique structural and electronic properties. This complex molecule belongs to a class of extended aromatic hydrocarbons with fused ring systems and strategically positioned phenyl groups, which influence its optical, electronic, and photophysical characteristics. The discovery and development of this molecule stem from the broader research into polycyclic aromatic hydrocarbons and their potential applications in high-performance electronic devices.

The initial research on the synthesis of 5,10,15,20-tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene focused on developing extended π-conjugated systems that can offer superior thermal and photostability. This compound was first reported in the context of designing materials for organic electronics and optoelectronic applications, particularly as candidates for organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). The extended conjugation, provided by the fused benzoperylene core, enhances the electron mobility and ensures high fluorescence quantum yields. The addition of tetraphenyl substituents helps modulate solubility and crystallinity, which are critical factors for processability in thin-film fabrication.

The synthesis of this compound typically involves multi-step procedures that include cyclization and aromatic substitution reactions. A common synthetic route starts from the preparation of precursor molecules through Suzuki or Stille coupling reactions. The cyclization steps are often achieved under high-temperature conditions, facilitating the formation of the complex fused-ring system. Researchers have refined these synthetic strategies to optimize yields and purity, making the material accessible for large-scale applications.

One of the most notable applications of 5,10,15,20-tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene is in the development of organic semiconductors. The molecule's high thermal stability and excellent electron-transport properties make it suitable for use in electronic devices that operate under high-stress conditions. It has been successfully integrated into OLEDs, where it functions as an efficient emitter material due to its strong fluorescence and long exciton lifetime. Furthermore, its use in OFETs has demonstrated significant potential, offering high charge carrier mobility, which is critical for achieving better device performance. This compound is also being explored for photovoltaic applications, where its broad absorption spectrum can enhance light-harvesting capabilities.

In addition to these practical applications, 5,10,15,20-tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene is of interest for fundamental research into π-conjugated systems. The molecule serves as a model compound for understanding the behavior of extended aromatic systems, including their electronic interactions, photophysical properties, and structural dynamics. Studies on this compound have contributed to advancing knowledge in the design of new organic materials with tailored properties for next-generation electronic and photonic devices.

Research continues to explore ways to further optimize the synthesis and functionalization of this molecule. Efforts are focused on improving its solubility, enhancing its charge transport properties, and developing derivatives with tunable electronic characteristics. As the demand for high-performance organic materials grows, 5,10,15,20-tetraphenylbisbenzo[5,6]indeno[1,2,3-cd:1',2',3'-lm]perylene remains a key compound with promising applications in cutting-edge technologies.