The path-selectivity and stereoselectivity of gridization pathways into fluorene-based Drawing Hand Grids (DHGs-F) are precisely modulated through tuning acid conditions and side-chain effects. BF3•OEt2 supports the realization of the gridization path (rac-DHG1-F, yield: 82%, meso-DHG1-F, yield: 11%). On the contrary, CF3SO3H will lead to the enhancements in polymerization pathways (about 85% yield). When the side chain is a methoxy group, rac-DHG1-F and meso-DHG1-F will be obtained. However, when the side chain is a group without an oxygen atom, only rac-DHG1-F can be obtained (de = 100%). Moreover, through excitonic physical proper-ties, rac-DHGs-F exhibits a more π-electronic delocalization, potentially serving as the intriguing tactic strategy to modulate the optoelectronic properties.