Several ruffled beta-to-ortho-phenyl monofused metalloporphyrins (M(II)MFPs) with 1,3-indanedione functionality have been synthesized by oxidative fusion of free base trans-chlorins via nickel insertion followed by the skeletal rearrangement of macrocycle. The synthesized monofused porphyrins exhibited red-shifted electronic spectral features as compared to precursor, trans-chlorins or structurally related unfused porphyrins (mono/tri-beta-substituted porphyrins) due to extended pi-conjugation and nonplanar conformation of the macrocyclic core. Four of the synthesized porphyrins were structurally characterized by X-ray diffraction analysis. Ring fusion resulted in twisted macrocyclic conformation, and the twist angles (the angle between 24-atom core and fused part) were found to be in the range of 20.97 degrees to 27.97 degrees. NiMFP(IND)Ph-2 (3b) exhibited modestly ruffled conformation of the macrocyclic core which was further confirmed by higher Delta 24 (0.362 angstrom) and Delta C-beta (0.279 angstrom) values. Free base monofused porphyrins have shown upfield shifted (Delta delta = 0.27-0.29 ppm) inner core NHs as compared to precursors (trans-chlorins), whereas much downfield shifted (Delta delta = 0.9 ppm) as compared to H2TPP. Electron-rich Ni(II) complexes, that is, NiMFP(IND)R-2 (where R = H and Ph) (1b and 3b), exhibited metal centered oxidation (Ni-II/Ni-III) due to extended pi-conjugation of macrocyclic core and electron-donating beta-substituents. Facile synthesis with good yields (60-90%), unexpected nickel-induced oxidative fusion, and selective conversion of trans-chlorins into monofused Ni-II-porphyrins are the significant features of the present work.