The cross-coupling reactions have been used in C-C bond formation which can be used extensively in optoelectronic materials for organic light emitting diode (OLED), organic photovoltaics and chemical biosensing. Here, we report twofold geminal C-C bond formation at 1,1-dibromoolefins via cross-coupling reactions of aromatic boronic esters over Pd catalysts for multiple topological configurations of π-conjugated molecules. We employ a series of recipes from a precursor toolbox to produce π-conjugated macrocycles, conjugated dendrimers, 1-dimensional linear conjugated polymers, 2-dimensional conjugated microporous polymers (CMPs) and crosslinking conjugated polymer nanoparticles (CCPNs). The π-conjugated macrocycles, dendrimers and 1-D polymers show characteristic aggregation-induced emission properties. 2-D conjugated microporous polymers possess unique porosity of 2-3 nm. This universal strategy toward definite topological configurations of π-conjugated molecules enables efficient coupling of aryl bromides with various coupling partners under mild conditions affording multiple topological conjugated systems with abundant optical and optoelectronic interest.