Instead, the excitation located in the dibenzotropylium cation ring leads to a positive charge redistribution, which approaches the anilinium ring and consequently causes an electrostatic repulsion towards the acidic proton. As a result, the acidity in the excited state is significantly increased, without a change in the local electronic structure in the proton donating anilinium moiety. Furthermore, the charge redistribution is triggered by an excited state antiaromatic character of the dibenzotropylium cation unit, which relocates the electron density to the lower part of the perimeter of its rings to relieve that destabilization. Thus, based on these computational results, we have identified the first example of a photoacidity originating by charge reorganization within a unit which is not interacting electronically with the proton donating group. The two units instead interact electrostatically. as well as their respective isolated solid samples.