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This works describes a new step into the assembly of molecular textiles by the use of covalent templating. To establish a well‐founded base and to tackle pre‐mature obstacles, expected during the fabrication of the desired 2D‐material, we opted to investigate the in‐solution synthesis of molecular patches e. g. cut‐outs of a textile. A bi‐functional cross‐shaped monomer was designed, synthesized and was in‐detail characterized by means of 1H‐NMR and chiro‐optical spectroscopy. In addition, x‐ray structure crystallography was used to assess the absolute configuration. The monomer was used in an in‐solution oligomerization to assemble the molecular patches via imine condensation, which revealed the formation of predominately dimeric patches. The imine‐oligomer mixtures were further analyzed by reduction and cleaved to investigate the conditions required post mono‐layer assembly. All reaction stages were followed by FT‐IR and 1H‐NMR analysis. Finally, we address the adsorption of the cross‐shaped monomer onto a Au(111) surface, via high vacuum electrospray deposition. The subsequent annealing of the interface induced the on‐surface imine condensation reaction, leading to unidimensional oligomers co‐adsorbed with clusters of cyclic‐dimers. Nc‐AFM analysis revealed the tridimensional molecular structures, and together with electrospray deposition technique showed to be a promising pathway to investigate potential monomer candidates. [ABSTRACT FROM AUTHOR]