ESI-MS/MS of expanded porphyrins: a look into their structure and aromaticity
authors Ramos, CIV; Figueira, F; Poleto, MD; Amado, FML; Verli, H; Tome, JPC; Neves, MGPMS
nationality International
journal JOURNAL OF MASS SPECTROMETRY
author keywords protonated expanded porphyrins; electrospray mass spectrometry; gas-phase; structure/aromaticity; Huckel systems; Mobius systems
keywords NONLINEAR-OPTICAL PROPERTIES; MASS-SPECTROMETRIC ANALYSIS; MOBIUS AROMATICITY; METAL-COMPLEXES; CONFORMATION; HEXAPHYRINS(1.1.1.1.1.1); IDENTIFICATION; ELECTROSPRAY; DERIVATIVES; HEXAPHYRIN
abstract Electrospray mass spectrometry/mass spectrometry was used to investigate the gas-phase properties of protonated expanded porphyrins, in order to correlate those with their structure and conformation. We have selected five expanded meso-pentafluorophenyl porphyrins, respectively, a pair of oxidized/reduced fused pentaphyrins (22 and 24 p electrons), a pair of oxidized/reduced regular hexaphyrins (26 and 28 p electrons) and a regular doubly N-fused hexaphyrin (28 p electrons). The gas-phase behavior of the protonated species of oxidized and reduced expanded porphyrins is different. The oxidized species (aromatic Huckel systems) fragment more extensively, mainly by the loss of two HF molecules. The reduced species (Mobius aromatic or Mobius-like aromatic systems) fragment less than their oxidized counterparts because of their increased flexibility. The protonated regular doubly fused hexaphyrin (non-aromatic Huckel system) shows the least fragmentation even at higher collision energies. In general, cyclization through losses of HF molecules decreases from the aromatic Huckel systems to Mobius aromatic or Mobius-like aromatic systems to non-aromatic Huckel systems and is related to an increase in conformational distortion. Copyright (C) 2016 John Wiley & Sons, Ltd.
publisher WILEY
issn 1076-5174
year published 2016
volume 51
issue 5
beginning page 342
ending page 349
digital object identifier (doi) 10.1002/jms.3760
web of science category Biochemical Research Methods; Chemistry, Analytical; Spectroscopy
subject category Biochemistry & Molecular Biology; Chemistry; Spectroscopy
unique article identifier WOS:000378524600003
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