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Review | Regular issue | Vol 87, No. 6, 2013, pp.1209-1240
Published online, 14th May, 2013
DOI: 10.3987/REV-13-769
SYNTHESIS AND CHARACTERIZATION OF TRIPHYRINS: A NEW FAMILY OF PORPHYRINOIDS

Daiki Kuzuhara and Hiroko Yamada*

*Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan

Abstract

This article reviews the recent reports about the syntheses, structures, photophysical and redox properties of newly synthesized [14]triphyrins(2.1.1), their metal complexes and their core-modified triphyrins, following the overview of the other triphyrin relatives containing three pyrrole rings and more than three methine carbons. Free-base [14]triphyrins(2.1.1) work as tridentate monovalent anionic cyclic ligands and a variety of metal complexes with Re(I), Mn(I), Ru(II), Pd(II), Pd(IV), Fe(II), Fe(III) and B(III) ions were obtained due to the flexible structure of the triphyrin macrocycles. The core-modified [14]triphyrin(2.1.1) was also expected, but the alkoxy-substituted compounds were obtained instead of the desired thiatriphyrin, probably because of the larger size of sulfur atom compared to nitrogen atom and the electronic repulsion between the lone pairs of inner nitrogen atoms.