An asymmetrically core-extended boron-dipyrromethene (BDP) dye was equipped with two electron-donating macrocyclic binding units with different metal ion preferences to operate as an ionically driven molecular IMPLICATION gate. A Na(+)-responsive tetraoxa-aza crown ether (R(2)) was integrated into the extended pi system of the BDP chromophore to trigger strong intramolecular charge transfer (ICT(2)) fluorescence and guarantee cation-induced spectral shifts in absorption. A dithia-oxa-aza crown (R(1)) that responds to Ag(+) was attached to the meso position of BDP in an electronically decoupled fashion to independently control a second ICT(1) process of a quenching nature. The bifunctional molecule is designed in such a way that in the absence of both inputs, ICT(1) does not compete with ICT(2) and a high fluorescence output is obtained (In(A)=In(B)=0-->Out=1). Accordingly, binding of only Ag(+) at R(1) (In(A)=1, In(B)=0) as well as complexation of both receptors (In(A)=In(B)=1) also yields Out=1. Only for the case in which Na(+) is bound at R(2) and R(1) is in its free state does quenching occur, which is the distinguishing characteristic for the In(A)=0 and In(B)=1-->Out=0 state that is required for a logic IMPLICATION gate and Boolean operations such as IF-THEN or NOT.

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