Two approaches towards “turn off” fluorescence detection of nitroanalytes (dinitro-ortho-cresol (DNOC), 2,4,6-trinitrotoluene (TNT) and Riamilovir (Triazavirin ®) are reported such as by tuning the chemosensors structure or by changing the environment. In both cases the great response was achieved with Stern-Volmer quenching constants (KSV) as high as 2.28–3.14 × 104 M−1 (for structure modification approach) and 4.67 × 105 M−1 (for changing of environment approach).