Study by liquid secondary ion and electrospray mass spectrometry of synthesized and formed‐in‐source metallocorroles

Barata, Joana F. B.; Barros, Cristina; Santana-Marques, M. Graça; Neves, Maria G. P. M. S.; Faustino, Maria A. F.; Tomé, Augusto C.; Correia, António; Cavaleiro, José A. S.

doi:10.1002/jms.1156

Cited by 12 publications

(11 citation statements)

References 43 publications

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“…Porphyrinoids are characterized by a great variety of structure types; hence, it is not possible to analyze them by using only one ionization method. There are many examples in the literature regarding the application of various MS ionization techniques [EI, [2,3] chemical ionization (CI), [4,5] electrospray ionization (ESI), [6][7][8][9][10][11] atmospheric pressure CI (APCI), [12][13][14] atmospheric pressure photoionization (APPI), [15][16][17][18] fast atom bombardment (FAB), [19][20][21] liquid secondary ion MS, [22,23] field desorption, [24][25][26] matrix-assisted laser desorption/ionization (MALDI) [19,27,28] ] with reference to this class of compounds. It is also possible to find examples of comparison of ionization methods in qualitative terms, but the number of such publications is very limited.…”

Section: Introductionmentioning

confidence: 99%

Comparison of the sensitivity of mass spectrometry atmospheric pressure ionization techniques in the analysis of porphyrinoids

et al. 2013

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The porphyrinoids chemistry is greatly dependent on the data obtained in mass spectrometry. For this reason, it is essential to determine the range of applicability of mass spectrometry ionization methods. In this study, the sensitivity of three different atmospheric pressure ionization techniques, electrospray ionization, atmospheric pressure chemical ionization and atmospheric pressure photoionization, was tested for several porphyrinods and their metallocomplexes. Electrospray ionization method was shown to be the best ionization technique because of its high sensitivity for derivatives of cyanocobalamin, free-base corroles and porphyrins. In the case of metallocorroles and metalloporphyrins, atmospheric pressure photoionization with dopant proved to be the most sensitive ionization method. It was also shown that for relatively acidic compounds, particularly for corroles, the negative ion mode provides better sensitivity than the positive ion mode. The results supply a lot of relevant information on the methodology of porphyrinoids analysis carried out by mass spectrometry. The information can be useful in designing future MS or liquid chromatography-MS experiments.

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Section: Introductionmentioning

confidence: 99%

Comparison of the sensitivity of mass spectrometry atmospheric pressure ionization techniques in the analysis of porphyrinoids

et al. 2013

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“…MS is a very powerful and sensitive analytical method. However, the number of publications related to the analysis of corroles using MS techniques is limited 18–20. Obviously, there are many examples in the literature regarding the use of various MS ionization techniques [EI, ESI, FAB, field desorption (FD), MALDI]4, 21 to confirm the molecular weight of prepared corroles.…”

Section: Introductionmentioning

confidence: 99%

Mass spectrometry studies on meso‐substituted corroles and their photochemical decomposition products

et al. 2010

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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.

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“…ESI‐MS has been extensively used to detect and characterize corroles mainly via accurate mass measurements. However, comprehensive studies of corroles using this technique are scarce although ESI‐MS may act as a strategic pointer for the bulk synthesis of novel porphyrinoid structures …”

Section: Introductionmentioning

confidence: 99%

Differentiation of aminomethyl corrole isomers by mass spectrometry

et al. 2012

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Two new isomeric aminomethyl corrole derivatives of [5,10,15-tris(pentafluorophenyl)corrolato]gallium(III) were synthesized with pyridine (py) molecules as axial ligands. When investigated by electrospray ionization mass spectrometry, in the positive and the negative ion modes, these compounds showed an unusual gas-phase behavior that could be used for their differentiation. In the positive ion mode, the differentiation was achieved through the formation of diagnostic fragment ions formed from [M-py + H](+) precursors, by (CH(3) )(2) NH and HF losses. An unusual addition of water to the main fragment ions provides an alternative route for isomer identification. Semi-empirical calculations were performed to elucidate the structures and stabilities of the main ionic species formed in the positive ion mode. In the negative ion mode isomer discrimination is accomplished via the fragmentation of the methoxide adduct ions [M-py + CH(3) O](-) through (CH(3) )(2) N(.) and HF losses.

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Study by liquid secondary ion and electrospray mass spectrometry of synthesized and formed‐in‐source metallocorroles

Cited by 12 publications

References 43 publications

Comparison of the sensitivity of mass spectrometry atmospheric pressure ionization techniques in the analysis of porphyrinoids

Comparison of the sensitivity of mass spectrometry atmospheric pressure ionization techniques in the analysis of porphyrinoids

Mass spectrometry studies on meso‐substituted corroles and their photochemical decomposition products

Differentiation of aminomethyl corrole isomers by mass spectrometry

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