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Synthesis and characterization of DA(8/1)OMe (14-{4Ј-[(methoxy)methoxy] biphenyl}-10,12-tetradecadiynoic acid) and DA(8/1)NBP (14-{4Ј-[(nitro)methoxy] biphenyl}-10,12-tetradecadiynoic acid ) are presented. Monolayers of DA(8/1)OMe at gaswater interface were investigated. It does not form a stable monolayer nor does it undergo polymerization at the gas-water interface. However, the Ba 2ϩ and Cd 2ϩ salts formed stable monolayer that polymerized. Polymerization was confirmed by Raman spectroscopy. The diacetylene analog with the more polar tail group, DA(8/1)NBP, does not form a monolayer and undergo polymerization regardless of the subphase condition. A mixed monolayer of DA(8/1)OMe and DA(8/1)NBP forms a true monolayer if the composition of DA(8/1)NBP is 50% or less.