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

Hemanta Kalita; Avijit Ghosh; Way Zen Lee; Mangalampalli Ravikanth

doi:10.1002/chem.201503905

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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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 H₂PO₄ ^- and CN^- ions, which was corroborated by absorption and fluorescence studies.

Original language	English
Pages (from-to)	2153-2157
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	6
DOIs	https://doi.org/10.1002/chem.201503905
Publication status	Published - 2016 Feb 5

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Ring Opening of a meso-Triaryl 25-Oxasmaragdyrin Macrocycle by m-Chloroperoxybenzoic Acid",

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 H2PO4 - and CN- ions, which was corroborated by absorption and fluorescence studies.",

keywords = "anion sensing, isosbestic point, meta-chloroperoxybenzoic acid, ring-opening reactions, smaragdyrin",

author = "Hemanta Kalita and Avijit Ghosh and Lee, {Way Zen} and Mangalampalli Ravikanth",

note = "Funding Information: We thank the Department of Science and Technology (DST), Government of India for financial support and H.K. thanks CSIR for a fellowship.",

year = "2016",

month = feb,

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doi = "10.1002/chem.201503905",

language = "English",

volume = "22",

pages = "2153--2157",

journal = "Chemistry - A European Journal",

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publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Ring Opening of a meso-Triaryl 25-Oxasmaragdyrin Macrocycle by m-Chloroperoxybenzoic Acid

AU - Kalita, Hemanta

AU - Ghosh, Avijit

AU - Lee, Way Zen

AU - Ravikanth, Mangalampalli

N1 - Funding Information: We thank the Department of Science and Technology (DST), Government of India for financial support and H.K. thanks CSIR for a fellowship.

PY - 2016/2/5

Y1 - 2016/2/5

N2 - 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 H2PO4 - and CN- ions, which was corroborated by absorption and fluorescence studies.

AB - 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 H2PO4 - and CN- ions, which was corroborated by absorption and fluorescence studies.

KW - anion sensing

KW - isosbestic point

KW - meta-chloroperoxybenzoic acid

KW - ring-opening reactions

KW - smaragdyrin

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