The targeted DTE 1o and the reference 2o (Figure ) are obtained via a convergent synthesis strategy, allowing their early functionalization at will (see ESI). The two thiophenic sides of the DTE 2o are firstly prepared separately through classical cross-coupling reactions. Finally, the two thiophene derivatives are bridged by the perfluorocyclopentene via stepwise nucleophilic substitutions. From 2o, the deprotection of the acetylenic arm followed by a Sonogashira crosscoupling with the 1-bromopyrene yields the bis-pyrene DTE 1o.