Redox Associated variation of Hückel Aromaticity from Lactam Embedded Smallest Antiaromatic trans-Doubly Nconfused Porphyrins: Synthesis and Characterization.

Nyancy, Halder and Mohandas, Sangeetha and Usharani, D. (2020) Redox Associated variation of Hückel Aromaticity from Lactam Embedded Smallest Antiaromatic trans-Doubly Nconfused Porphyrins: Synthesis and Characterization. Journal of Organic Chemistry, 85 (4). pp. 2059-2067.

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Abstract

High yield synthesis, spectroscopic and solid state structural proof of the lactam embedded smallest ever metal free stable Hückel antiaromatic trans-doubly N-confused [16] porphyrins are reported. These new facets of trans-doubly N-confused porphyrins have been anticipated to exhibit the redox associated variation of Hückel aromaticity as a mere consequence of the amido-like structures of the N-confused N-methyl pyrrole rings of the macrocycles. Strong aromaticity upon NaBH4 reduction leading to resonance dipolar structure of the [18]conjugated system as the reduced congener with concomitant Hückel topology are the important highlights. Excellent agreement between experimental spectroscopic measurements and the theoretically determined properties elucidate aromaticity switching upon chemical reduction. Recent years have witnessed an upsurge of demand for the experimental realization of stable antiaromatic systems due to their versatile applications in the material science. The conformational rigidity and the enriched stability of these novel 16 antiaromatic doubly N-confused porphyrins might entitle these macrocycles towards such applications.

Item Type:	Article
Uncontrolled Keywords:	Aromaticity, Pyrroles, Mixtures, Solvents, Macrocycles
Subjects:	500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 12 Aromatic Chemistry
Divisions:	Food Safety Analytical Quality Control Lab
Depositing User:	Food Sci. & Technol. Information Services
Date Deposited:	15 Jun 2020 04:29
Last Modified:	15 Jun 2020 04:29
URI:	http://ir.cftri.res.in/id/eprint/14380

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