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In connection with a study aimed at the evaluation of electronic effects in spiro-dicorrole (1a) and its binuclear Ni(II) complex (1b) we became interested in gem-dimethyl-substituted cyclotetrapyrrole (2a) and the corresponding Ni(II) complex (2b). Attempts to prepare 2a as the 12,13,16,17-tetraethyl-2,3,7, 8-tetramethyl derivative (5) by an acid-catalyzed(More)
The versatility of a resorcinol-substituted phenanthroline-strapped porphyrin was enhanced by appending allyl chains via a double Claisen rearrangement. Two pyridine arms were then appended to the resorcinol oxygens. This multifunctional porphyrin is a suitable generic building block for the preparation of liposoluble heme protein models. X-ray(More)
Viologens can exist in three redox states varying from dicationic to neutral. This work emphasizes the control of the host-guest properties in bis-viologen cyclophanes. Two flexible cyclophanes were prepared by a cyclisation method sensitive to the odd/even number of carbons in the flexible chains linking two viologens. C5 and C7 cyclophanes were(More)
[structure: see text] The synthesis of a Pacman heterobisporphyrin associating an octaethyl porphyrinatozinc (ZnOEP) energy donor and a triaryl porphyrinatozinc (ZntPP) energy acceptor around a calix[4]arene spacer is described. Contrary to previous symmetrical architectures, correlations between the chromophores in the unsymmetrical calixarene bisporphyrin(More)
[structure: see text] Based on the high affinity of phenanthroline-strapped porphyrins for imidazoles, building blocks for self-assembled, linear porphyrin architectures have been designed. Their synthesis is reported, and the assembly principle is illustrated by the formation of the shortest possible scaffold. Only one type of assembly is observed, and the(More)
Two self-complementary phenanthroline-strapped porphyrins bearing imidazole arms and C 12 or C 18 alkyl chains were synthesized, and their surface self-assembly was investigated by atomic force microscopy (AFM) on mica and highly ordered pyrrolitic graphite (HOPG). Upon zinc(II) complexation, stable porphyrin dimers formed, as confirmed by DOSY (1)H NMR and(More)
This study compares the behavior as cytochrome c oxidase (CcO) functional and structural models of a series of reported and unreported ligands that provide either a binding site for copper without a built-in proximal base, or both a flexible binding site for copper and a built-in proximal base, or a fixed binding site for copper with a built-in proximal(More)
The synthesis of a porphyrin rotaxane by dipolar cycloaddition takes advantage of the ditopic character of a phenanthroline-strapped porphyrin. The success of the click reaction was conditioned by the presence of both a coordinatively unsaturated metal in the porphyrin and a copper(I) bound to the phenanthroline, pointing at a new "tandem active metal(More)
The unique recognition properties of phenanthroline-strapped zinc porphyrin 1, which displays extremely high affinity for N-unsubstituted imidazoles, has been used as the driving force for the assembly of a photochemical dyad involving a zinc(II) porphyrin as energy donor and a free base porphyrin as energy acceptor. The synthesis of the(More)
The intramolecular π-dimerization between two 4,4'-bipyridinium cation radicals directly connected to the wide rim of a calixarene is described. The ability of a phenol-containing calixarene to dimerize in its two-electron-reduced state depends on a subtle balance of weak interactions associated with hydrogen bond formation on the lower rim and orbital(More)