The adoption of chlorine in drinking water disinfection with the determination of residual chlorine in the form of hypochlorite ion (ClO-) is in widespread demand. Several sensors including colorimetric, fluorometric, and electrochemical methods are currently in use, but detection limits and ease of application remain a challenge. In this work, two new cyanine derivatives-based ClO- sensors, that were prepared by solvent-free microwave synthesis, are reported. The two sensors are highly sensitive and selective to ClO-, exhibiting a noticeable color change visible to the naked eye. Additionally, the sensors can detect ClO- without interference from other potential water pollutants, with low detection limits of 7.43 ppb and 0.917 ppb based on absorption performance. When using fluorometric methods, the sensors' detection limits are pushed down to 0.025 ppb and 0.598 ppb for sensors I and II, respectively. The sensors can be loaded with paper strips for field and domestic detection of ClO- in tap water treatment installations. Using the quartz crystal microbalance (QCM) technique, these sensors showed strong detection sensitivity to ClO-, with detection limits of 0.256 ppm and 0.09 ppm for sensors I and II, respectively. Quantum chemical studies using density functional theory (DFT) calculations, natural bond orbital (NBO) analysis, molecular electrostatic potential (MESP), and time-dependent density functional theory (TD-DFT) supported the findings. The sensing mechanism is rationalized in terms of radical cation formation upon ClO- oxidation of cyanine sensors I and II.