One‐Pot Synthesis of Indene‐Expanded Porphyrins

Peterson, Geneva R.; Bampos, Nick

doi:10.1002/anie.200906580

Cited by 21 publications

(22 citation statements)

References 34 publications

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“…Thei dentification of the dipolar couplings between the NH (40,45)•••H (39,44) and NH (40,45)•••H (15,33) indicated the twisted rectangular conformation of the macrocycle with two pairs of flipped, and regular pyrrole rings ( Figure S100, S102, SI). Thec onformational rearrangement forced on [8-5-H] + upon second protonation, pushed the 18-Ph ring outside the cavity,r esulting in ac lose proximity of 18,36-ortho-Ph and NH (41,46), as evidenced by the NOE cross-peak. The syn-/ out-/out-o rientation of the naphthalene subunits was assumed based on the NOE criterion, supported by the lowest relative energy determined for this specific conformer (M4 in Figure S113, SI).…”

Section: Methodsmentioning

confidence: 99%

“…[23] Many of the expanded carbaporphyrinoids share structural features of an archetypical hexaphyrin [24,25] framework. Thus av ariety of hexaphyrinoids incorporating different carbocyclic subunits,for example,cyclohexene, [26] hexahydronaphthalene, [27] meta-, [13,[28][29][30][31][32][33] and para-phenylene, [33][34][35][36][37][38][39] biphenylene, [14] N-confused-, [40][41][42][43] and neo-confused pyrrole, [44,45] indene, [46] azulene, [47] pyridine, [48] phenanthrene, [22] and triphenylene were synthesized and studied. [49] Thenaphthiporphyrins,that is,carbaporphyrinoids incorporating an aphthalene ring, formally share attributes of both-regular size,a nd expanded porphyrinoids (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1)

et al. 2020

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rating two built-in 2,7-naphthylene moieties was synthesized as two separate,c onformationally locked stereoisomers.B oth conformers followed complex protonation pathwaysinvolving structurally different species,w hich can be targeted under kinetic and thermodynamic control. The neutralization of the ultimate dicationic product, accessible from both stereoisomers of the free base,allowed to realizethe complex conformational switching cycle involving six structurally different species.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1)

et al. 2020

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“…Although the scope of carbaporphyrinoids is constantly extending, the number of expanded porphyrins containing carbocyclic moieties is still limited in comparison with their smaller counterparts. Those systems are to date represented by azulisapphyrin, benzocarbasapphyrin, and dibenzoamethyrin, carbasapphyrin, N ‐confused heterosapphyrins, doubly N ‐confused sapphyrin derivatives, expanded benziporphyrinoids, and macrocycles with incorporated triphenylene motifs …”

Section: Introductionmentioning

confidence: 99%

Incorporation of a Phenanthrene Subunit into a Sapphyrin Framework: Synthesis of Expanded Aceneporphyrinoids

Szyszko

Małecki

Berlicka

et al. 2016

Chemistry A European J

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32-Hetero-5,6-dimethoxyphenanthrisapphyrins-macrocycles that link structural features of polycylic aromatic hydrocarbons and expanded porphyrins-were obtained in a straightforward [3+1] condensation reaction of dimethoxyphenanthritripyrrane and 2,5-bis(arylhydroxymethyl)heterocyclopentadienes. The highly folded conformation of formally 4 n π-electron macrocycles causes them to manifest only limited macrocyclic π conjugation as explored by means of NMR spectroscopic and X-ray structural analyses, and supported by DFT calculations. Although protonation does not change their π-conjugation characteristics, the cleavage of ether groups at the phenanthrenylene moiety yields nonaromatic 32-hetero-5,6-dioxophenanthrisapphyrins.

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“…Peterson und Bampos verçffentlichten die Synthese von [22]Dibenzocarbahexaphyrin(1.0.0.1.0.0) (Dibenzocarbaamethyrin) 87 (Schema 16). [85] Der Makrocyclus wurde aus Dipyrromethandicarboxylat und 2-Ethinylbenzaldehydi n einer Reaktionssequenz aus Decarboxylierung,K ondensation und Oxidation erhalten. Die Verbindung 87 zeigte in der 1 H-NMR-Spektroskopie Diatropizität.…”

Section: Expandierte 21-carbaporphyrine Benzocarbaporphyrine Und Azuunclassified

Expandierte Carbaporphyrinoide

Szyszko¹,

Latos‐Grażyński²

2020

Angewandte Chemie

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In diesem Aufsatz sollen die Fortschritte auf dem Gebiet der synthetischen expandierten Carbaporphyrinoide dargelegt werden. Die Entwicklung auf diesem Gebiet wird anhand von expandierten Porphyrin‐verwandten Systemen aufgezeigt, die eine Vielfalt von Bausteinen enthalten, mit deren Hilfe ein oder mehrere Kohlenstoffatome in die Kavität eingeführt werden. Die Ausführungen beginnen mit den Platyrinen – den Makrocyclen, die als Stammmolekül nicht nur der expandierten Carbaporphyrinoide, sondern der Klasse der Carbaporphyrinoide im Allgemeinen gelten. Nach einigen historischen Betrachtungen wird eine Vielzahl von expandierten porphyrinartigen Makrocyclen, die N‐fehlgeordnete oder neo‐fehlgeordnete Pyrrol‐Strukturelemente und verschiedene carbocyclische Untereinheiten enthalten, vorgestellt. Ein besonderer Schwerpunkt wird dabei auf die Anwendungen von expandierten Carbaporphyrinoiden in verschiedenen Bereichen gelegt, z. B. in der Organometallchemie, bei Schaltersystemen oder der Aromatizität. Abschließend wird ein kovalenter Käfig auf der Basis von expandierten Carbaporphyrinoiden vorgestellt.

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One‐Pot Synthesis of Indene‐Expanded Porphyrins

Cited by 21 publications

References 34 publications

Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1)

Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1)

Incorporation of a Phenanthrene Subunit into a Sapphyrin Framework: Synthesis of Expanded Aceneporphyrinoids

Expandierte Carbaporphyrinoide

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