Patterning perylenes on surfaces using thiol–ene chemistry

Abstract

This article describes the patterning of alkene-terminated perylenes on thiolated surfaces. A photochemical thiol–ene click reaction was locally induced (i) in the contact area between the stamp and the substrate, (ii) on surfaces, which were modified with thiolated nanolithographic patterns, immersed in solution and (iii) using a laser scanning confocal microscope over a thiolated substrate immersed in solution. The chemoselective attachment of the alkene-terminated perylenes was demonstrated. All patterning methods yielded homogeneous fluorescent patterns; while, the solution-based methods limit the presence of aggregates of perylenes. The patterns were characterized using atomic force microscopy, fluorescence spectroscopy and fluorescence lifetime measurements revealing monolayers of oriented perylenes in high coverages.