Despite the fundamental importance and broad applicability of E/Z dicarboxylic acids, their discrimination remains challenging and greatly unexplored. Herein, we present a general approach for the recognition of E/Z diacids using supramolecular interactions coupled with plasmonic response. The method allows detecting both single isomers and their light-induced interconversion, which ultimately entails multiple reversible nanoparticle aggregations. Such a molecular recognition-coupled responsive nanoscale self-assembly resembles natural mechanisms and can be a versatile means of building artificial complexity.