A series of novel network and ladder microporous polymers was prepared by conventional nucleophilic aromatic substitution polycondensation reaction between catechol-containing compounds and activated o-fluoro aryl monomers. The building blocks of these prepared polymers consist of rigid compounds such as triptycene, triphenylene or hexaazatriphenylene, which have unique structure properties that force the final product to adopt a large internal free volume within the structure and induce porosity. Also, a series of biphenyl-based polymers was prepared exploiting the severely rotationally hindered structure resulting from steric substitution. The preparation of microporous materials was extended further by using the macrocyclic compounds (such as phthalocyanine) as building blocks to synthesise several macrocyclic-based polymers, taking advantage of the ridged non-planar special geometry of the starting building blocks. The Yamamoto coupling reaction was used to prepare microporous polymers by the self-coupling of various aryl bromide compounds. The resulting polymers were characterised by their elemental and nitrogen adsorption analysis, which showed these materials to possess considerable surface area in each case. The prepared polymers exhibit good thermal stability as indicated by thermogravimetric analysis, the distinct sharing feature of all materials prepared in this study is the rigidity of the resulting polymer architecture originating from severely restricted rotational freedom along the polymer backbone.