A series of non-aromatic, stable [20π] di- para -benzihomoporphyrins containing two p -phenylene rings and two pyrrole rings as a part of homoporphyrin framework, were successfully synthesized by adopting [2 + 2] strategy as well as by cyclization of bilane type of precursor ( p -phenylene based tetrapyrrane). The [2 + 2] synthetic strategy afforded the di- para -benzihomoporphyrins in 6–10% yields and isolation of them by column chromatography was very tedious. Hence, we condensed the p -phenylene based tetrapyrrane, with wide range of aldehydes under mild reaction conditions and isolated the di- para -benzihomoporphyrins in 14–29% yields. The cyclization strategy was further extended to synthesize two examples of meso -BODIPYnyl di- p -benzihomoporphyrins. The di- p -benzihomoporphyrins were characterized and studied by high-resolution mass spectrometry, 1D and 2D NMR, absorption spectroscopy and DFT/TD-DFT techniques. The NMR studies indicated that the di- p -benzihomoporphyrins were nonaromatic in nature. The DFT studies revealed that the two p -phenylene rings were deviated by ∼50° from the mean plane because of which the π -conjugation in the di- p -benzihomoporphyrin macrocycles was restricted. Furthermore, the meso -pyridyl di- p -benzihomoporphyrin building block was used to generate the nonaromatic-aromatic dyad such as axially bonded di- p -benzihomoporphyrin-Zn(II)TTP dyad in solution and the formation of dyad was confirmed by 1D and 2D NMR spectroscopy.