Synthesis and First Studies of the Host–Guest and Substrate Recognition Properties of a Porphyrin‐Tethered Calix[6]arene Ditopic Ligand

Monnereau, Cyrille; Rebilly, Jean‐Noël; Reinaud, Olivia

doi:10.1002/ejoc.201001225

Cited by 25 publications

(7 citation statements)

References 73 publications

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“…Since the investigation of calixarenes dealing with their syntheses, reactivity and a large variety of applications is very intense, [55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70] only selected examples of considered compounds are described in this review.…”

Section: Resultsmentioning

confidence: 99%

Syntheses and reactivity of calixarenes functionalized at meso positions

Śliwa¹,

Deska²

2012

Arkivoc

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Section: Resultsmentioning

confidence: 99%

Syntheses and reactivity of calixarenes functionalized at meso positions

Śliwa¹,

Deska²

2012

Arkivoc

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“…14). 42 Comparison of this ditopic ligand with a mono amine evidenced higher stabilization (by two orders of magnitude) as anticipated by the presence of the second coordination site.…”

Section: Multipoint Recognition With Two Metal Centers Around a Cavitymentioning

confidence: 86%

Biomimetic cavity-based metal complexes

et al. 2015

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The design of biomimetic complexes for the modeling of metallo-enzyme active sites is a fruitful strategy for obtaining fundamental information and a better understanding of the molecular mechanisms at work in Nature's chemistry. The classical strategy for modeling metallo-sites relies on the synthesis of metal complexes with polydentate ligands that mimic the coordination environment encountered in the natural systems. However, it is well recognized that metal ion embedment in the proteic cavity has key roles not only in the recognition events but also in generating transient species and directing their reactivity. Hence, this review focuses on an important aspect common to enzymes, which is the presence of a pocket surrounding the metal ion reactive sites. Through selected examples, the following points are stressed: (i) the design of biomimetic cavity-based complexes, (ii) their corresponding host-guest chemistry, with a special focus on problems related to orientation and exchange mechanisms of the ligand within the host, (iii) cavity effects on the metal ion binding properties, including 1st, 2nd, and 3rd coordination spheres and hydrophobic effects and finally (iv) the impact these factors have on the reactivity of embedded metal ions. Important perspectives lie in the use of this knowledge for the development of selective and sensitive probes, new reactions, and green and efficient catalysts with bio-inspired systems.

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“…A porphyrin–quinolone conjugate was prepared similarly . A porphyrin-tethered calix[6]arene was synthesized through a click reaction of triazido calix[6]arene with (ethynylphenyl)porphyrin …”

Section: Reactions At Alkenes and Alkynes Bound To Porphyrinsmentioning

confidence: 99%

Synthesis and Functionalization of Porphyrins through Organometallic Methodologies

2016

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This review focuses on the postfunctionalization of porphyrins and related compounds through catalytic and stoichiometric organometallic methodologies. The employment of organometallic reactions has become common in porphyrin synthesis. Palladium-catalyzed cross-coupling reactions are now standard techniques for constructing carbon-carbon bonds in porphyrin synthesis. In addition, iridium- or palladium-catalyzed direct C-H functionalization of porphyrins is emerging as an efficient way to install various substituents onto porphyrins. Furthermore, the copper-mediated Huisgen cycloaddition reaction has become a frequent strategy to incorporate porphyrin units into functional molecules. The use of these organometallic techniques, along with the traditional porphyrin synthesis, now allows chemists to construct a wide range of highly elaborated and complex porphyrin architectures.

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Synthesis and First Studies of the Host–Guest and Substrate Recognition Properties of a Porphyrin‐Tethered Calix[6]arene Ditopic Ligand

Cited by 25 publications

References 73 publications

Syntheses and reactivity of calixarenes functionalized at meso positions

Syntheses and reactivity of calixarenes functionalized at meso positions

Biomimetic cavity-based metal complexes

Synthesis and Functionalization of Porphyrins through Organometallic Methodologies

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