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Title: | Versatile Synthetic Route for β-Functionalized Chlorins and Porphyrins by Varying the Size of Michael Donors: Syntheses, Photophysical, and Electrochemical Redox Properties |
Authors: | Grover, Nitika |
Keywords: | Chemistry Conformational Dynamics Deprotonation Reaction mechanisms Macrocycles |
Issue Date: | Sep-2017 |
Publisher: | ACS |
Abstract: | One-pot facile synthesis and characterization of novel β-substituted meso-tetraphenylporphyrins and/or chlorins were described. The high regioselective reactivity of active methylene compounds in Michael addition reaction was reported to access β-substituted trans-chlorins. Size-dependent approach was applied for the fine-tuning 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 β-substituents, whereas porphyrins exhibited higher mean plane deviation from 24-atom core (Δ24) as compared to chlorins. β-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 β-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. |
URI: | https://pubs.acs.org/doi/10.1021/acs.inorgchem.7b01158 http://dspace.bits-pilani.ac.in:8080/jspui/xmlui/handle/123456789/15194 |
Appears in Collections: | Department of Chemistry |
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