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Tailor made synthesis of the isomeric azoaromatics, HL1–HL4 [HL = (arylamino)phenylazopyridine] containing a single hydrophobic tail (Cn = C10 and C12) is described. The coordination induced C–N bond fusion synthetic protocol has been successfully used for the synthesis of the compounds, which are subsequently characterized using various spectroscopic techniques. The single crystal X-ray structure of compound HL4 has revealed that the hydrophobic chain in it orients itself with all-trans conformation of alkyl groups. Studies of their surface properties clearly demonstrate that these behave as surfactants. Amphiphilic properties of the compounds are followed by the studies of compression isotherms and their surface morphologies are studied with the use of high resolution field emission scanning electron microscopy (FE-SEM) as well as atomic force microscopy (AFM). Distinct differences in surface …