1-Methoxypyrene
[CAS# 34246-96-3]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: 1-Methoxypyrene
• Synonyms: 1-Hydroxypyrene methyl ether; 3-Methoxypyrene
• Molecular Formula: C₁₇H₁₂O
• Molecular Weight: 232.28
• CAS Registry Number: 34246-96-3
• SMILES: COC1=C2C=CC3=CC=CC4=C3C2=C(C=C4)C=C1

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.795, Calc.^*
• Boiling Point: 408.6±14.0 °C (760 mmHg), Calc.^*
• Flash Point: 165.7±9.4 °C, Calc.^*
• Index of Refraction: 1.795, Calc.^*
• Boiling Point: 408.6±14.0 °C (760 mmHg), Calc.^*
• Flash Point: 165.7±9.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Jacquignon, Pierre

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

1-Methoxypyrene is a polycyclic aromatic hydrocarbon derivative, where the pyrene core is substituted with a methoxy group at the 1-position. Pyrene itself is a well-known compound in organic chemistry, consisting of four fused benzene rings, and it serves as the parent structure for 1-methoxypyrene.

The discovery of 1-methoxypyrene is linked to studies on the chemical modifications of polycyclic aromatic hydrocarbons to improve their solubility and to tune their photophysical properties. The methoxy group attached to the pyrene core plays a critical role in altering the compound's electronic properties, particularly in terms of its absorption and emission spectra. These modifications enhance the compound's potential applications in various fields, including organic electronics and fluorescence-based technologies.

In terms of applications, 1-methoxypyrene has been primarily studied for its optical properties. It exhibits fluorescence, making it valuable in photonic devices and as a fluorescent probe in biochemical and environmental studies. The compound's fluorescence characteristics are utilized in fluorescence spectroscopy and imaging, as the pyrene core emits light upon excitation. These properties are especially useful in detecting and monitoring biological and environmental processes, where the compound can be employed in assays or as a marker.

Furthermore, 1-methoxypyrene has been studied in the context of its interactions with other molecules, including its use as a fluorescent marker for biological systems. The compound's ability to absorb light and re-emit it at a different wavelength makes it an ideal candidate for labeling applications, particularly in research involving molecular biology or material science.

In addition to its role in fluorescence-based applications, 1-methoxypyrene has also been investigated for its potential in organic light-emitting diodes (OLEDs) and solar cells. The pyrene-based structure contributes to the compound’s potential as a material for organic semiconductors, where the methoxy substitution helps improve the material's solubility and processing properties.

Overall, 1-methoxypyrene is an important compound in the field of organic electronics and fluorescence research. Its utility in various applications stems from its ability to interact with light in useful ways, and its role as a fluorescent probe makes it valuable in both scientific research and potential commercial technologies.

References

1997. 1-Methoxypyrene and 1,6-dimethoxypyrene: two novel metabolites in fungal metabolism of polycyclic aromatic hydrocarbons. Archives of Microbiology, 167(4).
DOI: 10.1007/s002030050449

2020. Biotransformation and Degradation Pathway of Pyrene by Filamentous Soil Fungus Trichoderma sp. F03. Water, Air, & Soil Pollution, 231(4).
DOI: 10.1007/s11270-020-04514-0

2022. Intrarenal 1-methoxypyrene, an aryl hydrocarbon receptor agonist, mediates progressive tubulointerstitial fibrosis in mice. Acta Pharmacologica Sinica, 43(11).
DOI: 10.1038/s41401-022-00914-6