2,2',7,7'-Tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene
[CAS# 207739-72-8]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 2,2',7,7'-Tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene
• Synonyms: Spiro-OMeTAD
• Molecular Formula: C₈₁H₆₈N₄O₈
• Molecular Weight: 1225.43
• CAS Registry Number: 207739-72-8
• SMILES: COC1=CC=C(C=C1)N(C2=CC=C(C=C2)OC)C3=CC4=C(C=C3)C5=C(C46C7=C(C=CC(=C7)N(C8=CC=C(C=C8)OC)C9=CC=C(C=C9)OC)C1=C6C=C(C=C1)N(C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC)C=C(C=C5)N(C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 243-248 °C (Expl.)
• Index of Refraction: 1.744, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

2,2',7,7'-Tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene is an organic compound with potential applications in the fields of materials science, electronics, and optoelectronics. This compound belongs to a class of spirobifluorene derivatives that exhibit unique properties, making them suitable for use in various advanced technologies. The molecular structure of 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene consists of a spirobifluorene backbone functionalized with four N,N-di(4-methoxyphenyl)amino groups. These groups, which act as electron-donating moieties, enhance the electronic properties of the compound, facilitating its use in electronic and optoelectronic devices.

The discovery of spirobifluorene compounds dates back to the early 20th century when researchers first synthesized and investigated their unique structural and electronic properties. These compounds have since gained attention due to their ability to exhibit high thermal stability, strong fluorescence, and excellent charge transport properties. The addition of electron-donating groups such as N,N-di(4-methoxyphenyl)amino further improves the performance of spirobifluorene derivatives in various applications.

The synthesis of 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene typically involves the introduction of the N,N-di(4-methoxyphenyl)amino groups onto the spirobifluorene scaffold through a series of chemical reactions. These reactions may include nucleophilic substitution and coupling reactions, which allow for the controlled functionalization of the spirobifluorene structure. The resulting compound exhibits enhanced solubility, stability, and electronic properties, making it suitable for incorporation into various materials.

One of the primary applications of 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene is in the development of organic light-emitting diodes (OLEDs). OLEDs are widely used in display technologies and lighting due to their ability to emit light efficiently when an electric current is applied. The compound's high electron-donating ability and its stable optical and electronic properties make it an ideal candidate for use as a hole-transporting material in OLEDs. By incorporating 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene into OLED devices, researchers can improve the efficiency, brightness, and longevity of the devices, leading to better performance in commercial applications.

In addition to OLEDs, this compound also shows promise in organic photovoltaic (OPV) devices, which are used for solar energy harvesting. The high charge mobility and good electronic properties of 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene make it suitable for use as an electron donor in OPV cells. By optimizing the structure of the material and its interactions with other components in the OPV device, researchers can enhance the power conversion efficiency of solar cells. The compound's role as an electron donor can improve the overall performance of the solar cells, making it a promising material for renewable energy applications.

Furthermore, the compound's excellent fluorescence properties make it suitable for use in fluorescent sensors and detection devices. The ability to emit light when exposed to certain wavelengths allows it to be used in applications such as chemical sensing and biological imaging. By modifying the structure and functional groups of the spirobifluorene derivative, researchers can tailor its fluorescence properties for specific detection purposes, expanding its potential applications in analytical chemistry and diagnostics.

The unique properties of 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene, including its high thermal stability, electron-donating functionality, and fluorescence, make it an important material in the development of advanced electronic and optoelectronic devices. As research in this area continues to progress, it is likely that new applications for this compound will emerge, particularly in the fields of energy harvesting, sensors, and display technologies.

References

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DOI: 10.1007/s40820-023-01046-0

2023. Surface Functionalization of Indium Tin Oxide Electrodes by Self-assembled Monolayers for Direct Assembly of Pre-synthesized SnO2 Nanocrystals as Electron Transport Layers. Electronic Materials Letters, 19(2).
DOI: 10.1007/s13391-022-00403-2

2024. Sustainability pathways for perovskite photovoltaics. Nature Materials, 23(8).
DOI: 10.1038/s41563-024-01945-6