Synthesis of 4-substituted catechols with side-chains of different C[double bond, length as m-dash]C bond number as urushiol analogues and their anticorrosion performance.

4-Substituted catechols with different C[double bond, length as m-dash]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[double bond, length as m-dash]C bond. The coating of the urushiol analogue bearing only one side chain C[double bond, length as m-dash]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.