A series of fluorene-based grid molecules (so-called Grid fluorenes) have been synthesized by means of shape-supported cyclization, starting from H-shaped precursors via the alternative Friedel-Crafts reactions of fluorenols and Suzuki cross-coupling reactions with key cyclization yields up to 26%. Fluorenol approaches and nanogrids open a door to soluble one-, two-, or three-dimensional nanoporous polymers as next-generation polymer mechano-semiconductors facing a new era of consciousness.