Adventures in corrole features by electrospray ionization mass spectrometry studies

Iglesias, Bernardo A.; Barata, Joana F. B.; Ramos, Catarina I. V.; Santana-Marques, M. Graça; Neves, Maria G. P. M. S.; Cavaleiro, José A. S.

doi:10.1039/c3ra47788f

Cited by 8 publications

(7 citation statements)

References 134 publications

(161 reference statements)

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“…A similar procedure was used to prepare the Zn(II) complex of meso -triphenylcorrole . The complexation of H 3 TPFC with several divalent transition-metal ions, including Zn 2+ , was studied by liquid secondary ion and electrospray mass spectrometry. , …”

Section: Functionalization At the Inner Core Positionsmentioning

confidence: 99%

“…185 The complexation of H 3 TPFC with several divalent transition-metal ions, including Zn 2+ , was studied by liquid secondary ion and electrospray mass spectrometry. 186,187 N-Alkyl corroles are easily metalated with zinc(II) acetate in pyridine to yield zinc(II) corrole complexes such as the Zn(II)(N(21)-benzyl-TPFC) (py) (52) and Zn(II)(N(21)picolyl-TPFC) (53) (Figure 12). 144,188 Metalation of the triply linked 2H-corrole dimers (with two inner NH groups in each corrole unit) 54a and 54b with Zn(OAc) 2 •2H 2 O in CHCl 3 at reflux for 20 h gave the bis(zinc(II)) complexes Zn54a and Zn54b in 76% and 79% yield, respectively (Scheme 10).…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Strategies for Corrole Functionalization

et al. 2016

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This review covers the functionalization reactions of meso-arylcorroles, both at the inner core, as well as the peripheral positions of the macrocycle. Experimental details for the synthesis of all known metallocorrole types and for the N-alkylation reactions are presented. Key peripheral functionalization reactions such as halogenation, formylation, carboxylation, nitration, sulfonation, and others are discussed in detail, particularly the nucleophilic aromatic substitution and the participation of corroles in cycloaddition reactions as 2π or 4π components (covering Diels-Alder and 1,3-dipolar cycloadditions). Other functionalizations of corroles include a large diversity of reactions, namely Wittig reactions, reactions with methylene active compounds, formation of amines, amides, and imines, and metal catalyzed reactions. At the final section, the reactions involving oxidation and ring expansion of the corrole macrocycle are described comprehensively.

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Section: Functionalization At the Inner Core Positionsmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

Strategies for Corrole Functionalization

et al. 2016

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“…Also, according to SciFinder, more than 70 reviews on selected aspects of corroles have been published over the last 2 decades, − although most of these publications would more accurately be classified as minireviews on very narrowly focused aspects of corrole chemistry or properties. Some of the above SciFinder-listed reviews on corroles have included discussions of the compound’s redox reactivity, − but none has been devoted exclusively to the electrochemical properties of corroles as a function of changes in the central metal ion, compound structure, or solution conditions.…”

Section: Introductionmentioning

confidence: 99%

Electrochemistry of Corroles in Nonaqueous Media

2016

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This review describes the known electrochemistry of corroles in nonaqueous media from 1980 until the present. The outline of the review is grouped according to the periodic table, proceeding from left to right, describing first monomeric free-base derivatives and then transition-metal compounds, followed by main-group corroles, before ending with a brief description of lanthanide and actinide corroles. Many similarities exist between the redox properties of metallocorroles and metalloporphyrins, but there are also many differences due, in part, to the different charges of the two conjugated macrocycles and the noninnocence of the corrole ligand in a variety of compounds. One part of this review will focus on describing redox behavior as a function of metal ion and axial ligands, while another will focus on how changes in structure of the macrocycle are associated with changes in redox behavior. It is hoped that this review will answer the majority of the readers' questions as to what has been electrochemically observed for corroles in the past while at the same time enabling the reader to utilize data in the literature to predict and "tune" what might be observed in future electrochemical studies of corroles that have yet to be synthesized and characterized.

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“…It is possible to monitor the reaction by ESI or MALDI mass spectrometry using the negative mode detection. Two reviews reported the best matrix and conditions to use when running MALDI/ TOF 279 or ESI 280 mass spectra for small molecules or corrole derivatives. Very interestingly, the UV-visible spectra of the isolated tetra-thiocyanatocorroles show, in acetonitrile, the presence of four Q-bands, quite similar to the Q-type bands of chlorophyll-a.…”

Section: Photodynamic Therapy (Pdt) Applicationsmentioning

confidence: 99%