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Chemistry. 2016 Feb;22(6):2153-2157. doi: 10.1002/chem.201503905. Epub 2016 Jan 08.

Ring Opening of a meso-Triaryl 25-Oxasmaragdyrin Macrocycle by m-Chloroperoxybenzoic Acid.

Chemistry (Weinheim an der Bergstrasse, Germany)

Hemanta Kalita, Avijit Ghosh, Way-Zen Lee, Mangalampalli Ravikanth

Affiliations

  1. Department of Chemistry, Indian Institute of Technology, Powai, Mumbai, 400076, India.
  2. Instrumentation Center, Department of Chemistry, National Taiwan Normal University, 88 Sec. 4 Ting-Chow Road, Taipei, 11677, Taiwan.
  3. Department of Chemistry, Indian Institute of Technology, Powai, Mumbai, 400076, India. [email protected].

PMID: 26749551 DOI: 10.1002/chem.201503905

Abstract

Smaragdyrin, a class of expanded porphyrin macrocycles, upon treatment with meta-chloroperoxybenzoic acid (mCPBA) underwent oxidative ring opening to form an unprecedented linear pentaheterocyclic compound. The linear pentaheterocyclic compound was freely soluble in common organic solvents and characterized in detail by HRMS, 1D and 2D NMR spectroscopy, and X-ray crystallography. Our preliminary studies indicated that the linear pentaheterocyclic compound can specifically sense anions such as H

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: anion sensing; isosbestic point; meta-chloroperoxybenzoic acid; ring-opening reactions; smaragdyrin

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