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Mass spectrometry studies on meso ‐substituted corroles and their photochemical decomposition products
Author(s) -
Świder Paweł,
NowakKról Agnieszka,
Voloshchuk Roman,
Lewtak Jan P.,
Gryko Daniel T.,
Danikiewicz Witold
Publication year - 2010
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1860
Subject(s) - chemistry , mass spectrometry , photochemistry , decomposition , organic chemistry , chromatography
Corroles, ring‐contracted analogs of porphyrins, are an important class of compounds which have attracted the attention of many researchers in the fields of organic, coordination and physical chemistry. In the present work, the stability and the decomposition pathways of a diverse set of meso ‐substituted corroles have been studied using mass spectrometry (MS), UV–Vis absorption and preparative methods combined with NMR spectroscopy. Four different ionization methods (electrospray ionization, field desorption, atmospheric pressure photoionization and atmospheric pressure chemical ionization) were utilized to investigate light‐ and oxygen‐induced decomposition in various solvents. It was found that the rate of decomposition in MeCN is significantly higher than in CH 2 Cl 2 , hexane, MeOH and ethyl acetate. HR‐MS combined with CID–MS/MS enabled us to identify the products of initial decomposition. Surprisingly, numerous smaller open‐chain compounds were also detected. Large‐scale decomposition of a corrole bearing sterically hindered substituents at positions 5 and 15 allowed us to isolate mg quantities of three decomposition products: isocorrole and isomeric biliverdin‐type species. These are formed as a result of oxygen attack on the meso ‐10 position. Copyright © 2010 John Wiley & Sons, Ltd.