Synthesis and modification of octafluoro[2.2]paracyclophane (parylene AF4)

Hicks, Craig; Duffy, Brendan; Hargaden, Gráinne C.

doi:10.1039/c4qo00110a

Cited by 9 publications

(5 citation statements)

References 42 publications

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“…[ 27 ] A diversity‐oriented synthesis of perfluoro‐ and brominated tetrafluoro‐PCPs as CVD precursors has also been developed. [ 28 ] Using sulfur‐extrusion of dithia[3.3]paracyclophane derivatives approach, 4,5,7,8‐tetrafluoro‐ and 4,5,7,8,12,13,15,16‐octafluoro‐PCP can be prepared with fluoro substitution at either one or both benzene rings of the PCP core. [ 29 ] Various substituted PCPs bearing trifluoroacetyl, maleimide, anhydride, [ 30 ] pentafluorophenol ester group, [ 31 ] and other different functionalized PCP monomers have been optimized for CVD (co)polymerization.…”

Section: General Overview Of Cyclophane‐based Cvd Polymerizationmentioning

confidence: 99%

Design Strategies for Structurally Controlled Polymer Surfaces via Cyclophane‐Based CVD Polymerization and Post‐CVD Fabrication

et al. 2022

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Molecular structuring of soft matter with precise arrangements over multiple hierarchical levels, especially on polymer surfaces, and enabling their post‐synthetic modulation has tremendous potential for application in molecular engineering and interfacial science. Here, recent research and developments in design strategies for structurally controlled polymer surfaces via cyclophane‐based chemical vapor deposition (CVD) polymerization with precise control over chemical functionalities and post‐CVD fabrication via orthogonal surface functionalization that facilitates the formation of designable biointerfaces are summarized. Particular discussion about innovative approaches for the templated synthesis of shape‐controlled CVD polymers, ranging from 1D to 3D architecture, including inside confined nanochannels, nanofibers/nanowires synthesis into an anisotropic media such as liquid crystals, and CVD polymer nanohelices via hierarchical chirality transfer across multiple length scales is provided. Aiming at multifunctional polymer surfaces via CVD copolymerization of multiple precursors, the structural and functional design of the fundamental [2.2]paracyclophane (PCP) precursor molecules, that is, functional CVD monomer chemistry is also described. Technologically advanced and innovative surface deposition techniques toward topological micro‐ and nanostructuring, including microcontact printing, photopatterning, photomask, and lithographic techniques such as dip‐pen nanolithography, showcasing research from the authors’ laboratories as well as other's relevant important findings in this evolving field are highlighted that have introduced new programmable CVD polymerization capabilities. Perspectives, current limitations, and future considerations are provided.

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Section: General Overview Of Cyclophane‐based Cvd Polymerizationmentioning

confidence: 99%

Design Strategies for Structurally Controlled Polymer Surfaces via Cyclophane‐Based CVD Polymerization and Post‐CVD Fabrication

et al. 2022

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“…For the deposition of thin film AF4 parylene coatings, vapor deposition polymerization (VDP) based on the Gorham process is used since it produces homogenous films and covers small holes and edges very well. The VDP process seen in Figure 1b needs solid dimers, which become sublimated over 100 • C. This vapor is then pyrolyzed over 600 • C and only fluorinated monomers are left for the final step, where the polymerization of AF4 takes place on the substrate material at room temperature [1,18,20,21]. Since parylene AF4 offers such outstanding properties, research was conducted on using it as a dielectric barrier coating for MEMS applications [22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Assessment of AF4 Parylene Cohesion/Adhesion on Si and SiO2 Substrates by Means of Pull-Off Energy

2023

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Advanced packaging solutions require insulation and passivation materials with exceptional properties which can also fulfill the reliability needs of electronics devices such as MEMS, sensors or power modules. Since bonding (cohesive/adhesive) properties of packaging coatings are very important for reliable functioning of electronics devices, the bonding of aliphatic fluorinate-4 (AF4) parylene coatings was assessed in this work. As there is a lack of data regarding its bonding towards different substrates, pull-off tests of 1.6 and 2.5 µm thick AF4 coatings on silicon (Si) and glass (SiO2) substrates were performed. These showed a clear difference in the pull-off F/s curves between the AF4 coatings on Si and SiO2 substrates. This difference is parameterized by the pull-off energy, which will be presented in this work. To further understand the origin of the distinction in the pull-off energies between the AF4-Si and AF4-SiO2 samples and subsequently the cohesive/adhesive properties, mechanical and structural characterization was conducted on the AF4 coatings, where a clear difference in the E-modulus and crystallinity was observed. The Si and SiO2 wafers were shown to facilitate the CVD growth of the AF4 film distinctively, which likely relates to the divergent thermal properties of the substrates. Understanding of the cohesive/adhesive properties of AF4 coatings on different substrate materials advances the usage of the AF4 in electronics packaging technologies.

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“…3,9,15,16 Parylene AF4 is usually manufactured from the process of chemical vapor deposition (CVD) using 1,1,2,2,9,9,10,10-octafluoro [2.2]paracyclophane (known as AF4) as a precursor. 3,14,17 Therefore, AF4 should be prepared to manufacture parylene AF4. However, the fluorinated structure in AF4 makes its manufacturing procedure more complicated.…”

Section: Introductionmentioning

confidence: 99%

“…Parylene polymers have been widely used as a coating material. − The application has been expanded in the aerospace, military, medical, semiconductor, and display industries, − due to many features and advantages of parylene such as low dielectric constant, high thermal stability, low moisture absorption, and long-term UV stability. ,− There are many variations of parylene depending on their chemical structure: parylene C, parylene D, parylene N, and parylene HT (or parylene AF4) . Among these polymers, parylene AF4 has especially received growing attention because the fluorinated structure in parylene AF4 improves its physicochemical properties significantly compared to other parylene polymers. ,,, Parylene AF4 is usually manufactured from the process of chemical vapor deposition (CVD) using 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (known as AF4) as a precursor. ,, Therefore, AF4 should be prepared to manufacture parylene AF4. However, the fluorinated structure in AF4 makes its manufacturing procedure more complicated.…”

Section: Introductionmentioning

confidence: 99%

Solubility Measurement and Recrystallization Process Design for 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane (AF4) Purification

Kim

Park

Chang

et al. 2019

Crystal Growth & Design

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In this study, a single-step recrystallization process for purifying 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (AF4) was investigated. The existing AF4 purification method consists of three steps. Among the steps, methanol washing has a problem of dissolving AF4, so the production yield is around 60%. To improve the yield of AF4 without decreasing its purity, a recrystallization process is suggested, and its feasibility was analyzed by measuring AF4 solubility in each prescreened solvent. Both cooling and antisolvent crystallization were investigated to determine which method would be suitable for the recrystallization process by measuring the purity of the AF4 product. In the results, cooling crystallization with chloroform showed the best performance in terms of 92.31% of the maximum obtainable yield and 99.98% purity in the AF4 purification process. However, antisolvent crystallization showed a high maximum obtainable yield, but very low purity. Therefore, compared to the existing method (60% yield and 99% purity), the suggested cooling recrystallization with chloroform as the solvent is more appropriate for the AF4 purification process.

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Synthesis and modification of octafluoro[2.2]paracyclophane (parylene AF4)

Cited by 9 publications

References 42 publications

Design Strategies for Structurally Controlled Polymer Surfaces via Cyclophane‐Based CVD Polymerization and Post‐CVD Fabrication

Design Strategies for Structurally Controlled Polymer Surfaces via Cyclophane‐Based CVD Polymerization and Post‐CVD Fabrication

Assessment of AF4 Parylene Cohesion/Adhesion on Si and SiO2 Substrates by Means of Pull-Off Energy

Solubility Measurement and Recrystallization Process Design for 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane (AF4) Purification

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