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Amphiphilic disc-shaped penta-alkynes were studied with regard to their molecular organization in Langmuir-Blod- gett (LB) mono- and multilayers. It was found that each compound investigated forms edge-on arranged stable monolayers at the air-water interface. LB-multilayers derived from fivefold pentyl-substituted pentaynes are characterized by an edge-on ordering of the molecules within Y-type bilayers. One of these compounds, containing a hydoxy substituent as hydrophilic head group, is exemplified and two possible rectangular molecular assemblies perpendicular to the substrate, each with a columnar in-plane packing, will be discussed as a result of molecular modelling. Based on the experimental results, hexagonal layer packing in the LB-film of a disc-shaped penta-alkynyl carboxylic acid without lateral substituents proved to be possible, which, furthermore, could be confirmed by molecular mechanics simulation.