We demonstrated the design and photophysical properties of a dual-state emissive π-conjugated dipyridyl-dipyrroethene chromophore (6) synthesized via selective diformylation of (E)-dipyrroethene followed by condensation with 2-amino pyridine. The rational molecular design, incorporating both hydrogen bonding and π···π interactions, leads to a unique supramolecular architecture in the solid state, and the system exhibits aggregation-induced emission properties. We further extend the applicability of chromophore 6 for the selective detection of serum albumin.