Faculty Publications
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Item Meso-tris(2-furyl/2-thienyl) substituted porphyrin-ferrocene ‘click’ conjugates: synthesis, experimental, and computational studies(Royal Society of Chemistry, 2024) Shet, S.N.; Patil, M.; Shetti, V.S.The chemical synthesis of 5-(4-azidophenyl)-10,15,20-tris(2-furyl/2-thienyl)porphyrins and their utilization in a Cu(i) catalyzed alkyne-azide ‘click’ reaction (CuAAC) with ethynylferrocene to obtain the hitherto unknown meso-tris(2-furyl/2-thienyl) substituted porphyrin-ferrocene ‘click’ conjugates are reported. These new ‘click’ conjugates were studied along with the reference ‘click’ conjugates containing all-meso-aryl substituted porphyrins by experimental and computational methods. Compared to the reference, the new conjugates displayed red-shifted absorption/emission bands, easier porphyrin ring reduction, and an efficient photoinduced electron transfer (PET) process from ferrocene to a porphyrin unit. Density functional theory (DFT) calculations performed on these conjugates revealed a good correlation with the experimental results. © 2024 The Royal Society of Chemistry.Item Porphyrin-azoheteroarenes: synthesis, photophysical, and computational studies(Royal Society of Chemistry, 2025) Shet, S.N.; Bhat, V.G.; Swathi, S.G.; Udayakumar, U.; Shetti, V.S.Azobenzenes (Ph-N = N-Ph) are well-known photochromic compounds with widespread applications. Replacing one or both phenyl rings of azobenzenes with heteroarenes leads to a new class of compounds known as azoheteroarenes (Het-N N-Ph/Het). Azoheteroarenes have gained attention as promising alternatives to traditional azobenzenes in the field of photopharmacology due to their ability to undergo photoswitching under visible light. Interestingly, the chemistry of porphyrin-containing azoheteroarenes has been underexplored. In this study, we present the synthesis of hitherto unknown hybrid molecules: porphyrin-azopyrroles (porphyrin-N N-pyrrole) and porphyrin-azoindoles (porphyrin-N N-indole), which also feature porphyrins with five-membered meso-substituents, such as 2-furyl and 2-thienyl groups. The porphyrin-azoheteroarenes with meso-tris(2-furyl/2-thienyl) substitutions demonstrate red-shifted absorption and emission bands, more significant Stokes shifts, and smaller optical bandgaps compared to hybrids containing only meso-aryl groups. Additionally, these porphyrin-azoheteroarenes exhibit higher fluorescence emission intensities than their corresponding precursor porphyrins. © 2025 The Royal Society of Chemistry.