Organic redox systems are molecules that are both investigated for fundamental purposes (electron transfer processes and reactivity) and used in applied materials science (conducting materials, photovoltaic devices, batteries or spintronic). A common strategy to design such compounds is to link two heteroatoms through a π-bridge displaying an even number of sp 2 carbon atoms. 2 Such derivatives are called "Weitz type" redox systems and typically display three stable redox states. Among them, tetrathiafulvalene and methyl-viologens (MV) are the most widely used electron donors and electron acceptors, respectively. Although the applicability of this strategy to phosphorus as the single heteroatom was postulated back in 1978, 2 organophosphorus multi-stage Weitz-type redox derivatives were described by our group in 2020 only (Fig. ). In that work, we reported a family of dicationic P-containing Polycyclic Aromatic Hydrocarbons (PAHs), such as A (Fig. ) which displays three stable redox states including a radical cation. In contrast to MV, which are poorly luminescent, their intense luminescence was used in electrofluorochromic devices emitting in both the visible and near infrared domains. This illustrated that the Weitz-strategy adapted to P-derivatives is an original way to obtain intrinsically switchable electroactive fluorophores and overcome some limitations of widely used compounds such as MV. In order to prepare similar fluorophores which properties could be addressed upon oxidation (rather than reduction, as for A), a stable bis-ylide linked by an even number of sp 2 C has to be prepared according to general formula displayed in Fig. . In the field of conjugated ylide, the λ 5phosphinines (also called λ 5 -phosphabenzene) recently appeared as a powerful building block for optoelectronic, following the pioneering observations by Müller et al. Indeed, their intense luminescence was used in various optoelectronic devices such as organic light-emitting diodes and organic lasers. In particular, the 2,6-dicarbonitrile diphenyl-1-λ 5 -phosphinine scaffold (DCNP, blue heterocycle in B, Fig. ), firstly developed by emerged as particularly interesting due to its straightforward synthesis, high stability, and easily tunable optical properties. However, their redox properties remain underexplored.