Synthesis of hexaphyrins and N-fused pentaphyrins bearing pyridin-4-ylsulfanyl groups

abstract

In recent years much attention has been devoted to expanded macrocyclic chemistry. Nevertheless, while several advancements were achieved in the synthesis of novel expanded porphyrin architectures, not much has been developed in the functionalization of these macrocycles. This report shows the selective replacement of the p-fluorine atoms of meso-pentakis(pentafluorophenyl) N-fused [22]pentaphyrin and meso-hexakis(pentafluorophenyl) [26]hexaphyrin with 4-mercaptopyridine moieties, thus increasing their potential as ligands for coordination chemistry and catalysis or electronic transfer applications striving new synthetic methodologies and a new set of specific applications for this type of compounds.

keywords

NONLINEAR-OPTICAL PROPERTIES; EXPANDED PORPHYRINS; PHOTODYNAMIC INACTIVATION; PHOTOPHYSICAL PROPERTIES; CATIONIC PORPHYRINS; MOBIUS AROMATICITY; SAPPHYRIN; PLATFORM

subject category

Chemistry

authors

Figueira, F; Farinha, ASF; Tome, AC; Cavaleiro, JAS; Paz, FAA; Tome, JPC

our authors

acknowledgements

We thank Fundacao para a Ciencia e a Tecnologia (FCT, Portugal), the European Union, QREN, FEDER through the COMPETE program; QOPNA research unit (project PEst-C/QUI/UI0062/2013; FCOMP-01-0124-FEDER-037296) and CICECO associated Lab (PEst-C/CTM/LA0011/2013; FCOMP-01-0124-FEDER-037271) for their general funding scheme. We further wish to thank FCT for funding the R&D project PTDC/CTM/101538/2008. F. Figueira, and A. Farinha thank FCT for their doctoral (SFRH/BD/46788/2008) and post-doctoral (SFRH/BPD/73060/2010) fellowships, respectively.

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