Synthesis of N-fused dithia and dibenzi homoporphyrins. Issue 6 (1st February 2022)

• Record Type: Journal Article
• Authors: Sengupta, Rima; Isar, Prosenjit; Ravikanth, Mangalampalli
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 6(2022)
• Page Start: 1580
• Page End: 1588
• Publication Date: 2022-02-01
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01946e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : N-Fused dithia and dibenzi homoporphyrins have been reported and NMR spectroscopy, absorption spectroscopy, X-ray crystallography and DFT/TD-DFT analyses suggested the non-aromatic nature of the molecules. Abstract : N-Fused dithia and dibenzi homoporphyrins have been synthesized using a [2 + 2] approach by condensing one equivalent of appropriate dithienyl/di p -phenylene ethene diol with one equivalent of N-confused dipyrromethane in CH2 Cl2 under mild acid catalysed conditions. The X-ray structure obtained for the N-fused dibenzi homoporphyrin revealed that the fused tripentacyclic ring was planar and was tilted by an angle of 11.35° whereas the p -phenylene moieties were highly deviated by angles of 48.70° and 50.93° from the mean plane defined by five meso carbon atoms. The NMR and absorption features suggested the non-aromatic nature of both N-fused dithia and dibenzi homoporphyrins. The DFT studies revealed that the N-fused dithia homoporphyrin was highly distorted with one thiophene ring facing outside the macrocyclic cavity. The spectral features of both N-fused dithia and dibenzi homoporphyrins were supported by TD-DFT studies.