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In the boundary lubrication regime, the addition of long as well as straight alkyl chain containing additive exhibit a serendipitous impact on protecting various metallic surfaces or machinery components from friction and subsequent wear. In quest of environment-friendly, proficient friction-reducing, surface protective and cost-effective lubricant additives; herein, two diazomethine functionalised long-chain consisting organic molecules, namely (3E)-N-((E)-2-(octadecylimino)ethylidene)octadecan-1-amine (ODE) and (3E)-N-((E)-2-(dodecylimino)ethylidene)dodecan-1-amine (DDE) were synthesized through a one-pot condensation reaction. The surface protective film-forming, as well as wear and friction reducing properties of these organic additives on steel balls within paraffin oil (PO), were thoroughly explored using a four-ball tester with variation in time, load and speed. The addition of these additives showed a remarkable reduction of coefficient of friction (COF) and wear amount in compared to the pure base oil. ODE exhibited better performance with a ∼62% reduction in COF and ∼23% reduction in wear amount for steels in contact. Electronic level analysis for elucidating the tribofilm formation capability of the additives was rationalized using computational approaches such as density functional theory (DFT) and Fukui indices. Additionally, the molecular dynamics (MD) simulation which is an efficient computational approach was used to explore the spontaneous adsorption insight of additives; and also radial distribution function (RDF) were analysed to impressively explore the molecular-level interactions and adsorption mechanism of the additives with the metal atoms. Thereby, the mechanism of surface adhesive tribofilm formation and its metal protection capability has been explained in a comprehensive manner. Diazomethine functionalised organic molecules were synthesized with a variation of aliphatic chain length. Long aliphatic chain containing ODE additive showed enhanced surface protective performances in paraffin oil exhibiting lower COF value in comparison to DDE. Possible formation of ODE-based efficient tribofilm in metal-solution interface which exhibits enhanced surface adsorption property on the metal surface. Substantial decrease in wear upon addition of ODE in the base oil, which was confirmed by FE-SEM and 3D surface profilometer study. MD simulation has been used to investigate the adsorption competence of ODE and DDE on the iron surface. [ABSTRACT FROM AUTHOR]