Bis-vinylogous Corrole: The First Expanded Corrole

Paolesse, Roberto; Khoury, Richard G.; Sala, Fabio Della; Natale, Corrado Di; Sagone, Francesco; Smith, Kevin M.

doi:10.1002/(sici)1521-3773(19990903)38:17<2577::aid-anie2577>3.0.co;2-g

Cited by 19 publications

(17 citation statements)

References 9 publications

(14 reference statements)

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“…A novel and intriguing example of dicorrole species (57) has been recently reported by Vogel and co-workers [70]. In this so-called spirodicorrole the two macrocyclic moieties are linked trough a spiro center at the 10 position and consequently they are present as isoforms.…”

Section: Spirodicorrolementioning

confidence: 96%

“…The exact route for the formation of (57) has not been completely elucidated, but it needs the elimination of a carbon dioxide unit. The comparison of the electronic spectra of (57) and (59) revealed bathochromic shifts and changes in the relative spectral intensities of the absorption bands, which can be attributed to the presence of spiroconjugation. To further study the effect of spiroconjugation on the spectroscopic properties of (57), Vogel and co-workers were also successful in the preparation of the Ni(II) complex of the isocorrole (59), the first of this kind of isomeric form of corrole, prepared by the oxidative cyclization of the Ni complex of a,c-biladiene (60), (Fig.…”

Section: Spirodicorrolementioning

confidence: 98%

See 1 more Smart Citation

Novel Aspects of Corrole Chemistry

Nardis¹,

Monti²,

Paolesse

2005

MROC

Self Cite

147

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Corrole is one of the first examples of porphyrin analogs reported in the literature. This class of compounds has received a great attention, because of their promising exploitation in different fields, ranging from medicine to material chemistry. Among them, corrole can be considered the prototypical example of contracted porphyrins, with one of the meso carbon bridges missing. Although this macrocycle was first reported more than thirty years ago, only recently more attention has been devoted to the chemistry of corrole. The recent availability of efficient and facile syntheses of meso-substituted corroles has probably been the shuttle for the impressive flourishing of corrole-related papers appearing in literature in the last few years. The aim of this review is to highlight the latest reports in the synthetic chemistry of corrole, with special attention to the synthetic strategies and peripheral functionalizations of this macrocycle.

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Section: Spirodicorrolementioning

confidence: 96%

Section: Spirodicorrolementioning

confidence: 98%

Novel Aspects of Corrole Chemistry

Nardis¹,

Monti²,

Paolesse

2005

MROC

Self Cite

147

View full text Add to dashboard Cite

show abstract

“…In 1999, Paolesse, Smith, and co-workers reported the synthesis of a bisvinylogous corrole, [22]porphyrin(3.1.3.0) (16), which they described as the first expanded corrole. [34] Strictly speaking, this is not formally true since, depending on the definition employed, such venerable systems as sapphyrin, rubyrin, and even porphyrin and its isomers constitute "expanded corroles". Nonetheless, macrocycle 16 represents an important new addition to the expanded porphyrin family.…”

Section: [22]porphyrin(3130)mentioning

confidence: 99%

Synthetic Expanded Porphyrin Chemistry

2003

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Expanded porphyrins are synthetic analogues of the porphyrins, and differ from these and other naturally occurring tetrapyrrolic macrocycles by containing a larger central core with a minimum of 17 atoms, while retaining the extended conjugation features that are a hallmark of these quintessential biological pigments. The result of core expansion is to produce systems with novel spectral and electronic features, interesting and, often unprecedented, cation-coordination properties, and, in many cases, an ability to bind anions in certain protonation states. Also adding to the appeal of expanded porphyrins is their central role in addressing issues of aromaticity. In many cases, they also display structural features, such as decidedly nonplanar "figure-eight" motifs, that have no antecedents in the chemistry of porphyrins or related macrocyclic compounds. In this Review, the various synthetic approaches now being employed to produce expanded porphyrins as well as their various applications-related aspects are discussed.

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“…Such molecules, which break records of the diatropic ring current, were advertized as "superarenes" [18]. They constitute a branch of expanded porphyrins, placed between rigid porphyrins and conformationally unstable non-bridged annulenes [19][20][21][22][23][24].…”

Section: Porphyrin Vinylogsmentioning

confidence: 99%