Novel chemosensors that are azo dyes bearing coumarin with indole and thiophene recognition moieties were synthesized. Sensor properties of the dyes were investigated within multiple basic environments that include various pH ranges, anions, and organic amines. Recognition of the basic media by the chemosensors that have acidic NH and NH2 groups, occurs via the deprotonation process which was supported with reversibility study and H-1 NMR experiments. The Density Functional Theory calculations have employed to support the experimental results. Chemosensors 6a and 6b showed remarkable detection ability in a pH range of 7-11 and they have been also successfully utilized in the determination of CN- in semi-aqueous media.