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We demonstrate the potential of perylene bisimide (PBI) for label-freesensing of organic molecules by investigating the change in electronicproperties of five symmetric and asymmetric PBI derivatives, which share acommon backbone, but are functionalised with various bay-area substituents.Density functional theory was combined with a Greens function scatteringapproach to compute the electrical conductance of each molecule attached to twogold electrodes by pyridyl anchor groups. We studied the change in theirconductance in response to the binding of three analytes, namely TNT, BEDT-TTFand TCNE, and found that the five different responses provided a uniquefingerprint for the discriminating sensing of each analyte. This ability tosense and discriminate was a direct consequence of the extended {\pi} system ofthe PBI backbone, which strongly binds the analytes, combined with thedifferent charge distribution of the five PBI derivatives, which leads to aunique electrical response to analyte binding.

Exploiting the Extended {\pi}-System of Perylene Bisimide for Label-free Single-Molecule Sensing