Side Selection of the Fifth Coordinate with a Single Strapped Zinc(II) Porphyrin Host:  Full Characterization of Two Imidazole Complexes

Froidevaux, Jérôme; Ochsenbein, Philippe; Bonin, Michel; Schenk, Kurt; Maltese, P.; Gisselbrecht, Jean Paul; Weiss, Jean

doi:10.1021/ja9723646

Cited by 33 publications

(45 citation statements)

References 19 publications

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“…54 Weiss and coworkers designed a phenanthroline-strapped Zn-porphyrin as a specific binding site for imidazole through cooperative coordination and hydrogen bonding interactions. 121 Thus, an imidazolyl-appended phenanthroline-strapped Zn-porphyrin formed a self-complementary dimer (K = 10 9 M −1 ), and its dimer 74 formed a linear multiporphyrin array as a soluble oligomer and insoluble precipitates, as observed by diffusion ordered (DOSY) NMR and AFM, respectively (Scheme 33). 122…”

Section: Linear Multiporphyrin Arraysmentioning

confidence: 99%

Supramolecular Organization of Porphyrins and Phthalocyanines by Use of Biomimetic Coordination Methodology

Morisue¹,

Kobuke²

2014

Handbook of Porphyrin Science (Volume 32)

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Section: Linear Multiporphyrin Arraysmentioning

confidence: 99%

Supramolecular Organization of Porphyrins and Phthalocyanines by Use of Biomimetic Coordination Methodology

Morisue¹,

Kobuke²

2014

Handbook of Porphyrin Science (Volume 32)

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“…This shift, which results from a πÀπ interaction between the imidazole and the phenyl ring bearing H o , is characteristic of imidazole binding within the phenanthroline strap. 19 Only the inÀin conformer accounts for the upfield shift of the H o peak.…”

Section: Articlementioning

confidence: 99%

Highly Linear Self-Assembled Porphyrin Wires

et al. 2011

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An efficient noncovalent assembly process involving high geometrical control was applied to a linear bis(imidazolyl zinc porphyrin) 7Zn, bearing C(18) substitutents, to generate linear multiporphyrin wires. The association process is based on imidazole recognition within the cavity of the phenanthroline-strapped zinc porphyrin. In chlorinated solvents, discrete soluble oligomers were obtained after (7Zn)(n) was end-capped with a terminal single imidazolyl zinc porphyrin derivative 4Zn. These soluble species, as well as their destabilization in the presence of protic solvents, were studied by UV-visible and time-resolved luminescence. In the solid state, assemblies as long as 480 nm, which corresponds to 190 iterative units or a total of 380 porphyrins, were observed by atomic force microscopy measurements on mica. The length and linearity of the porphyrin wires obtained illustrate the potential of phenanthroline-strapped porphyrins for the directional control of self-assembly processes.

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“…According to these general principles, 1 HNMR and UV/Vis spectroscopy studies of [1 Zn] have converged to show that pyridine or N-alkyl imidazoles are exclusively bound at the open face of [1 Zn]. [29] However,o wing to the presence of the hydrogen-bond-accepting imine functions of thes trap, the receptor exhibitsh ighly selective recognition properties of N-unsubstituted imidazoles, binding these ligandsw ithin the phen pocket. 1 HNMR spectroscopy observations are sufficient to determinet he coordination site of an axial base.…”

Section: Metallic Structures and Inclusion Complexesmentioning

confidence: 99%

From Models of Hemoproteins to Self‐Assembled Molecular Wires

2017

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In nature, the various properties of tetrapyrrolic macrocycles are mostly due to their proteic environment and result from an evolutionary process that is difficult to reproduce during the lifetime of a synthetic chemist. Thus, the task of synthetic chemists attempting to reproduce the biological role of porphyrin architectures, which perform functions from catalysis to light harvesting, is complicated. This account describes how a phenanthroline‐strapped porphyrin architecture initially designed to afford new hemoprotein models led, over the last two decades, to the preparation of highly linear self‐assembled nano‐objects inspired by light‐harvesting architectures. The approach summarized herein mimics, in a very modest way, the polyvalence of tetrapyrrolic macrocycles found in nature.

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Side Selection of the Fifth Coordinate with a Single Strapped Zinc(II) Porphyrin Host: Full Characterization of Two Imidazole Complexes

Cited by 33 publications

References 19 publications

Supramolecular Organization of Porphyrins and Phthalocyanines by Use of Biomimetic Coordination Methodology

Supramolecular Organization of Porphyrins and Phthalocyanines by Use of Biomimetic Coordination Methodology

Highly Linear Self-Assembled Porphyrin Wires

From Models of Hemoproteins to Self‐Assembled Molecular Wires

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