Suitable conformations and proper alignment of complex natural macrocycles are essential for achiev-ing their unique properties. However, such artificial macrocycle prototypes are still limited due to syn-thetic difficulties. In this respect, directly linked por-phyrin analog dimers display tunable conformations and intriguing properties, and thus, they may be employed as a class of promising platforms. Herein, we report that one-pot oxidative dimerization of thia-hydrosapphyrin 1 yields dimers, 2anti and 2syn, com-prising a transoid-oriented plate-like bipyrrolo[1,2-a] indolylidene. The thiophene-containing tetrapyrrole arching subunits in 2 lie at the opposite (anti) and same (syn) sides of the plate, respectively. Meanwhile, multiply fused cisoid-orientated dimer 3 was also obtained; a polycyclic pyrrolo-bridged bipyrroloin-dole derivative tethered with fully pi-conjugated bridges was formed. Notably, the anti-dimer 2anti underwent subsequent oxidative fusion to furnish a further-fused [6.5.5.7.5.5.5.6]-octacyclic compound 4anti. In contrast, the syn-orientated 2syn could not be further fused due to the long distance between the potential reaction sites. This study provides a unique approach to the fused dimeric porphyrin analogs for potential near-infrared optical materials by a simple oxidation reaction. It also reveals the importance of conformation-modulated reactivity for constructing complex porphyrin arrays.