Acid-catalyzed benzoylation reactions of Diels-Alder polyphenylenes

Journal Article · Sat Oct 27 00:00:00 EDT 2018 · Polymer

DOI:https://doi.org/10.1016/j.polymer.2018.10.060· OSTI ID:1595017

Fujimoto, Cy ^[1]; Sorte, Eric ^[1]; Bell, Nelson ^[1]; Poirier, Cassandria ^[1]; Park, Eun Joo ^[2]; Maurya, Sandip ^[2]; Lee, Kwan-Soo ^[2]; Kim, Yu Seung ^[2]

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1. Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
2. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

In this work, post-polymerization reactions of Diels-Alder polyphenylene with ring-substituted benzoyl chloride derivatives using triflic acid as the catalyst, effected selective Friedel-Crafts acylation of the lateral phenyl groups attached to the polyphenylene backbone. Using 4-(trifluoromethyl) benzoyl chloride gave a polymer with increased hydrophobicity. Using 4-fluorobenzoyl chloride afforded lateral 4-(fluorobenzoyl)phenyl substituents, which were further functionalized by nucleophilic aromatic substitution of the reactive fluoro substituent by 4-methoxyphenol.

• Research Organization: Sandia National Lab. (SNL-NM), Albuquerque, NM (United States); Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
• Sponsoring Organization: USDOE Office of Electricity (OE); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Hydrogen Fuel Cell Technologies Office; USDOE National Nuclear Security Administration (NNSA)
• Grant/Contract Number: AC04-94AL85000; AC52-06NA25396; NA0003525
• OSTI ID: 1595017
• Alternate ID(s): OSTI ID: 1636124
• Report Number(s): SAND-2019-14445J; 682638
• Journal Information: Polymer, Vol. 158, Issue C; ISSN 0032-3861
• Publisher: Elsevier
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Poly(phenylene)
Friedel Crafts
Fluorine