Rational and controllable syntheses of variants of modified N-confused N-fused porphodimethenes and a porphotrimethene with adaptive properties

Manik, Jana and Sumit, Sahoo and Sanjay, Kottekad and Usharani, Dandamudi and Harapriya, Rath (2024) Rational and controllable syntheses of variants of modified N-confused N-fused porphodimethenes and a porphotrimethene with adaptive properties. Dalton Transactions, 53. pp. 7397-7405.

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Abstract

Retrosynthetic design and synthesis with structural isolation of two unprecedented core modified N-confused N-fused porphodimethene-like porphyrinoids possessing a [5.5.5.5] tetracyclic ring with tunable photophysical properties is reported. The solid-state X-ray crystal structure reveals the expected cis geometry for the meso-sp3 carbons. Controlled chemical oxidation of the porphodimethene analogue 11 bearing the N-confused pyrrole moiety to the corresponding porphotrimethene 12 has been achieved in quantitative yield, while 10 bearing the N-methyl N-confused pyrrole moiety remained unsusceptible to chemical oxidation. All three S2N3 hybrid N-confused N-fused porphodi(tri)methene-like porphyri- noids 10–12 could recognize the fluoride anion with high selectivity; however, porphodimethene 10 and porphotrimethene 12 do so via deprotonation rather than an anion recognition based mechanism as has been anticipated in the case of porphodimethene 11.

Item Type:	Article
Uncontrolled Keywords:	Retrosynthetic design, functional porphyrin
Subjects:	500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 24 Organic Chemistry
Divisions:	Food Safety Analytical Quality Control Lab
Depositing User:	Somashekar K S
Date Deposited:	09 Dec 2025 11:51
Last Modified:	09 Dec 2025 11:51
URI:	http://ir.cftri.res.in/id/eprint/20172

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