1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane
[CAS# 3345-29-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane
• Synonyms: 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene
• Molecular Formula: C₁₆H₈F₈
• Molecular Weight: 352.22
• CAS Registry Number: 3345-29-7
• EC Number: 639-791-8
• SMILES: C1=CC2=CC=C1C(C(C3=CC=C(C=C3)C(C2(F)F)(F)F)(F)F)(F)F

Properties

• Melting point: 240-250 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H413
• Safety Statements: P261-P272-P273-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane is a fluorinated derivative of the [2.2]paracyclophane family, known for its unique structure featuring two benzene rings bridged by two ethylene groups. The octafluoro substitution, where fluorine atoms replace hydrogen atoms at key positions, enhances the compound’s chemical and physical properties, especially in terms of stability, reactivity, and resistance to environmental factors. This compound has found significant applications in materials science, particularly in the fabrication of advanced polymers, coatings, and electronic components.

The discovery of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane builds on research into paracyclophanes, which were first synthesized in the mid-20th century to explore the properties of molecules with unusual geometries. The inclusion of fluorine atoms, a highly electronegative element, imparts greater chemical resistance and alters the electronic structure of the molecule, making it highly attractive for applications that demand durability and precision. The fluorination of [2.2]paracyclophane was developed as part of efforts to create new materials with enhanced thermal stability, lower dielectric constants, and improved surface properties.

One of the most significant applications of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane is in the field of vapor deposition processes for the production of fluorinated poly(p-xylylene) films. These films, often referred to as Parylene AF, are deposited via chemical vapor deposition (CVD), where the octafluoro[2.2]paracyclophane is vaporized and decomposed into reactive monomers that polymerize on surfaces to form a protective, conformal coating. This process creates thin films with exceptional chemical inertness, hydrophobicity, and dielectric properties, making them ideal for applications in microelectronics, semiconductors, and aerospace technologies.

In electronics, the use of Parylene AF coatings derived from octafluoro[2.2]paracyclophane is particularly valuable for protecting delicate components from moisture, chemicals, and electrical interference. The low dielectric constant of these fluorinated polymers minimizes energy loss and interference in high-frequency circuits, which is critical for the miniaturization and performance optimization of modern electronic devices. Additionally, the films' chemical resistance makes them suitable for harsh environments, including those encountered in space exploration and advanced industrial settings.

The biomedical field has also benefited from the properties of octafluoro[2.2]paracyclophane. Fluorinated Parylene coatings are biocompatible and can be used to coat medical devices such as stents, implants, and surgical tools. These coatings ensure that medical instruments remain sterilized and functional, even when exposed to bodily fluids or harsh sterilization processes. The inert nature of the coating prevents interactions with biological tissues, reducing the risk of adverse reactions during medical procedures.

Another important application of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane is in the development of hydrophobic and anti-fouling surfaces. Due to the strong carbon-fluorine bonds, surfaces coated with polymers derived from this compound exhibit excellent water repellency and resistance to contamination. This property is highly desirable in industries ranging from maritime to clean energy, where preventing the buildup of contaminants on surfaces is essential for maintaining efficiency and performance.

Research into octafluoro[2.2]paracyclophane continues to explore its potential in nanotechnology, optical devices, and advanced coatings. The compound's ability to form robust, highly durable films with exceptional properties positions it as a key material for the next generation of high-performance coatings and polymers.

References

2010. Vapor pressures and sublimation enthalpies of seven pseudo-ionic liquids. The Journal of Chemical Thermodynamics, 42(5).
DOI: 10.1016/j.jct.2009.11.013