Immobilization of a hexaphyrin(1.0.1.0.0.0) derivative onto a tentagel-amino resin and its use in uranyl cation detection

Melfi, Patricia J.; Camiolo, Salvatore; Lee, Jeong Tae; Ali, Mehnaaz F.; McDevitt, John T.; Lynch, Vincent M.; Sessler, Jonathan L.

doi:10.1039/b718627d

Cited by 24 publications

(17 citation statements)

References 26 publications

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“…This step is known for other macrocyclic porphyrinoids with less reactive tetrapyrrole ligands and is usually performed by the action of tfa/HCl/H 2 O [10] or by alkaline hydrolysis with KOH, methanol and thf. [9] In the case of 6 and 7, however, both protocols result in a rapid and complete decomposition of the material, even if performed under the exclusion of air and light.…”

Section: Attempted Hydrolyses Of the Methyl Propionate Groups Of 6 Andmentioning

confidence: 99%

“…[8] Such a bipyrrole can be found in the patent literature [9] as part of the preparation of the functionalized porphycene in Scheme 1, and very recently the details of an eight-step synthesis of this bipyrrole have been published. [10] However, the functionalized bipyrrole has so far been used almost exclusively as a precursor to metalloporphycenes, [11] and only two examples of expanded porphyrinoids derived from this building block are present in the literature (Scheme 1). [10,12] In drolyze the methyl ester moieties were successful only for the manganese corrole and yielded a buffer-soluble, hemeanalogous corrole complex.…”

Section: Introductionmentioning

confidence: 99%

“…[10] However, the functionalized bipyrrole has so far been used almost exclusively as a precursor to metalloporphycenes, [11] and only two examples of expanded porphyrinoids derived from this building block are present in the literature (Scheme 1). [10,12] In drolyze the methyl ester moieties were successful only for the manganese corrole and yielded a buffer-soluble, hemeanalogous corrole complex. The dinuclear BF 2 chelate [bis(bodipy)], on the other hand, decomposes unselectively under the applied conditions.…”

Section: Introductionmentioning

confidence: 99%

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Functional Porphyrinoids from a Biomimetically Decorated Bipyrrole

et al. 2008

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The known 5,5′‐diformyl‐3,3′‐bis(methoxycarbonylethyl)‐4,4′‐dimethyl‐2,2′‐bipyrrole was employed in the preparation of biomimetic functional porphyrinoids. Tetrapyrrolic 2,2′‐bidipyrrins could be obtained from condensations with two equivalents of 3,4‐dialkyl‐2‐methylpyrroles. From these compounds, a manganese(III) corrole as well as a boron‐containing bis(bodipy) fluorophor are accessible as functional species in one‐step reactions. Both products were investigated by means of X‐ray crystallography. Attempts to hydrolyze the methyl ester moieties were successful only for the manganese corrole and yielded a buffer–soluble, heme‐analogous corrole complex. The dinuclear BF2 chelate [bis(bodipy)], on the other hand, decomposes unselectively under the applied conditions. A rationale for this decomposition was derived from crystallographic work on a related hydrolysis product with a F–B–O–B–F moiety. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Attempted Hydrolyses Of the Methyl Propionate Groups Of 6 Andmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Functional Porphyrinoids from a Biomimetically Decorated Bipyrrole

et al. 2008

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“…In contrast, the formation of uranyl, neptunyl, and dinuclear copper(II) complexes of isoamethyrin was accompanied with a change of the oxidation level to a [22]annulenoid structure corresponding to the hypothetical free base 33a-H 2 . [57,213,219] …”

Section: Rings With Up To Two Meso Bridgesmentioning

confidence: 98%

“…Amethyrins (31a-H 4 ) [55,[214][215][216][217] and their isomers isoamethyrins (32a-H 4 ) [57,213,218,219] possess two meso bridges in their structure (t F = 1.12). These macrocycles have [24]annulenoid substructures and are hence antiaromatic.…”

Section: Rings With Up To Two Meso Bridgesmentioning

confidence: 99%

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

2011

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The aromatic character of porphyrins, which has significant chemical and biological consequences, can be substantially altered by judicious modifications of the parent ring system. Expansion of the macrocycle, which is achieved by introducing additional subunits, usually increases the so-called free curvature of the ring, leading to larger angular strain. This strain is reduced by a variety of conformational changes, most notably by subunit inversion and p surface twisting. The latter effect creates a particularly convenient access to Möbius aromatic molecules, whose properties, predicted over 40 years ago, are of considerable theoretical importance. The conformational processes occurring in porphyrin analogues are often coupled to other chemical phenomena, and can thus be exploited as a means of constructing functional molecular devices. In this Review, the structural chemistry of porphyrinoids is discussed in the context of their conformational dynamics and p-electron conjugation.

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Supramolecular and Macrocyclic Chemistry of the Actinides

Mei

Lan

et al. 2018

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Supramolecular chemistry is the field of chemistry beyond molecules, and mainly focuses on systems made up of a number of discrete molecular subunits or components assembled through noncovalent forces such as electrostatic and hydrophobic interactions, hydrogen bonding, halogen bonds, and π–π interactions. Supramolecular chemistry deals with issues related to self‐assembly processes, a major issue in actinide‐related supramolecular chemistry. Metal–ligand coordination in which the bonds are of moderate bonding strength is essentially also one of the noncovalent interactions that are suitable for constructing supramolecular systems. Similar to transition metal and lanthanide‐based systems, there are many kinds of supramolecular assembly architectures actinide polyrotaxanes, actinide‐coordination‐driven closed or circular architectures as well as supramolecular systems involving weak interactions based on actinide–ligand interactions. In the field of supramolecular chemistry, macrocyclic compounds take up quite a large portion of research concerning with self‐assembly and metal coordination. The excellent complexation capacity of these macrocyclic compounds has made them promising candidates for the construction of actinide‐macrocyclic assemblies and the extraction and separation of actinides.

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Immobilization of a hexaphyrin(1.0.1.0.0.0) derivative onto a tentagel-amino resin and its use in uranyl cation detection

Abstract: The synthesis of an isoamethyrin derivative containing two CH 2 CH 2 CO 2 CH 3 moieties in the b-pyrrolic positions and its use in the colorimetric detection of the uranyl cation after immobilization onto a solid support is reported.

Cited by 24 publications

References 26 publications

Functional Porphyrinoids from a Biomimetically Decorated Bipyrrole

Functional Porphyrinoids from a Biomimetically Decorated Bipyrrole

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

Supramolecular and Macrocyclic Chemistry of the Actinides

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