A modular approach for the synthesis of Kekule diradicaloids is reported. The key step is the insertion of a carbene, namely a cyclic (alkyl)(amino)carbene (CAAC), into the C-H bonds of two terminal alkynes linked by a spacer. Subsequent hydride abstraction, followed by two-electron reduction of the corresponding bis(iminium) salts, affords the desired diradicaloids. This synthetic route readily allows for the installation of communicating spacers, featuring different degrees of aromaticity and lengths, and gives the possibility of generating unsymmetrical compounds with two different CAACs. EPR, NMR, UV-VIS and X-ray studies in combination with quantum-chemical calculations give insight into the electronic nature of the deeply colored Kekule diradicaloids. They feature a singlet ground-state with varying degree of diradical character in combination with small singlet/triplet gaps. Upon lengthening of the spacer, the properties of the compounds approach those of mono-radicals in which steric protection of the propargyl radical moiety is necessary to inhibit decomposition pathways. Most of these diradicaloids are stable at room tem-perature, both in solution and in the solid state, but are highly oxygen sensitive. They represent the first diradicaloids derived from iminium salts.