meso-Substituted expanded porphyrins: new and stable hexaphyrins

Neves, Maria G. P. M. S.; Martins, Rosalia M.; Tomé, Augusto C.; Silvestre, Armando J. D.; Silva, Artur M. S.; Félix, Vítor; Cavaleiro, José A. S.; Drew, Michael G. B.

doi:10.1039/a808952c

Cited by 197 publications

(86 citation statements)

References 6 publications

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“…[211] An unusual feature of the [28]hexaphyrin 41c-H 4 , isolated alongside 40c-H 2 in 1999, was that its 1 H NMR spectrum indicated the presence of a diatropic ring current, in spite of a 4n-electron conjugation pathway. [236] This striking observation remained a mystery until nine years later, when the solution structure of 41c-H 4 was reinvestigated by means of lowtemperature NMR spectroscopy and other physical methods. [121,123] It was shown that 41c-H 4 rapidly switches among four equivalent Möbius conformations (T1) in such a way that the positions of inverted rings in the intermediate T0 AD structure are retained (Scheme 17).…”

Section: 1)mentioning

confidence: 98%

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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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Section: 1)mentioning

confidence: 98%

“…In particular, the initial structural report on a perfluorophenyl species 40c-H 2 [236] revealed a T0…”

Section: 1)mentioning

confidence: 99%

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

2011

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“…Surprisingly, upon heating, [36]octaphyrin (1.1.1.1.1.1.1.1) bis-Cu II complex 132 was quantitatively split into two Cu…”

Section: Splitting Reactionsmentioning

confidence: 99%

“…[36] We subsequently reported the facile one-pot synthesis of the series of meso-aryl-substituted expanded porphyrins, including 3. [37] This result allowed us to embark on a systematic investigation on the chemistry of meso-aryl expanded porphyrins.…”

Section: Brief Historymentioning

confidence: 99%

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Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities

2011

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The chemistry of expanded porphyrins, which are higher homologues of porphyrins, has been intensively explored for the last three decades. Expanded porphyrins exhibit structures, electronic properties, coordination chemistry, and reactivities that are entirely different from those of porphyrins. Through these studies, it has become increasingly apparent that expanded porphyrins are attractive in views of aromaticity and multimetal coordination, or as functional dyes, nonlinear optical materials, ion receptors, or stable organic radicals. As such, we have continuously witnessed the emergence of expanded porphyrins that exhibit unprecedented structures and properties, as is highlighted by the facile realization of Möbius aromatic and even antiaromatic systems with twisted molecular structures. In this Review, the recent progress of the chemistry of expanded porphyrins after the seminal Review by Sessler and Seidel in 2003 is presented.

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Structural Diversity in Rubyrins: X-ray Structural Characterisation of Planar and Inverted Rubyrins

et al. 2000

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meso-Substituted expanded porphyrins: new and stable hexaphyrins

Cited by 197 publications

References 6 publications

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

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

Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities

Structural Diversity in Rubyrins: X-ray Structural Characterisation of Planar and Inverted Rubyrins

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