Synthesis of 4-substituted catechols with side-chains of different C&z.dbd;C bond number as urushiol analogues and their anticorrosion performance

• Published in: RSC advances Vol. 11; no. 28; pp. 16955 - 16961
• Main Authors: Wei, Zeng-Feng, Ni, Li-Jie, Quan, Heng, Duan, Jiang
• Format: Journal Article
• Published: 07.05.2021
• ISSN: 2046-2069
• DOI: 10.1039/d1ra01195b

4-Substituted catechols with different C&z.dbd;C bonds as urushiol analogues were synthesized through the a three-step route including reductive amination reaction of 3,4-dihydroxybenzaldehyde with N -Boc-piperazine, Boc deprotection, and amidation with various fatty acids. Electrochemical polymerization of these analogues on a copper surface afforded robust coatings with desirable adhesive force, hydrophobicity and thermal stability. Cyclic voltammetry and infrared spectroscopic characterizations revealed that the coating formation of urushiol analogues resulted from the electrooxidation-induced radical coupling of phenoxyl radicals with a phenyl ring and the side chain C&z.dbd;C bond. The coating of the urushiol analogue bearing only one side chain C&z.dbd;C bond exhibited the best performance in copper corrosion inhibition, with an inhibition efficiency of 99.99% and long-term effect (99.9% after 4 weeks of immersion in 3.5 wt% NaCl). The desired performance of these urushiol analogues suggests that they could be of practical applications as an alternative to the resource-limited natural urushiol. Reductive amination reaction was achieved on a catechol ring, leading to urushiol analogues that could be electropolymerized with desirable urushiol-like performance.