One-pot facile synthesis and characterization of novel beta-substituted meso-tetraphenylporphyrins and/or chlorins were described. The high regioselective reactivity of active methylene compounds in Michael addition reaction was reported to access beta-substituted trans-chlorins. Size dependent approach was applied for the fine-timing of product formation from porphyrins to chlorins. Notably, we were able to isolate mono/trisubstituted porphyrin and/or di/tetra-substituted chlorin from one-pot synthesis for the first time in porphyrin chemistry. Single-crystal X-ray diffraction analysis revealed the quasiplanar to moderate nonplanar conformation of chlorins due to trans orientation of beta-substituents, whereas porphyrins exhibited higher mean plane deviation from 24-atom core (Delta 24) as compared to chlorins. beta-Functionalized chlorins exhibited lower protonation constants and much higher deprotonation constants as compared to porphyrins revealing the combined effect of the conformation of macrocyclic core and the electronic nature of beta-substituents. Facile synthesis of porphyrins and/or chlorins based on the size of Michael donor employed and in turn resulted in tunable photophysical and electrochemical redox properties are the significant features of the present work.