Supramolecular assembly of organic molecules have emerged as an important strategy for developing functional materials for various applications including organic electronics. Eventhough they allows variation in the structures formed depending upon the building blocks used, these structures often lack kinetic stability which limits their applications. Herein we synthesize two novel Macrocyclic Diacetylene (MDA) derivatives; MDA-Amide and MDA- Ester and study their self assembly properties in the air-water interface using Lanmuir compression method. Owing to the π – π stacking of phenyl moieties and diacetylene templates in the macrocyclic ring, unidirectional organic nanotubes are generated upon langmuir compression mediated self assembly. Upon UV irradiation these tubes formed by monomeric MDA derivatives are covalently stabilized by the addition polymerization of diacetylene bond along the tubes. The dynamics of these organic fiber formations were affected by varying the subphase temperature during compression.