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Ring Opening of a meso ‐Triaryl 25‐Oxasmaragdyrin Macrocycle by m ‐Chloroperoxybenzoic Acid
Author(s) -
Kalita Hemanta,
Ghosh Avijit,
Lee WayZen,
Ravikanth Mangalampalli
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503905
Subject(s) - ring (chemistry) , chemistry , medicinal chemistry , stereochemistry , organic chemistry
Smaragdyrin, a class of expanded porphyrin macrocycles, upon treatment with meta ‐chloroperoxybenzoic acid ( m CPBA) 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 2 PO 4 − and CN − ions, which was corroborated by absorption and fluorescence studies.