Repozytorium

Incorporation of a phenanthrene subunit into a sapphyrin framework: synthesis of expanded aceneporphyrinoids.

Autorzy

Bartosz Szyszko

Marcin Małecki

Anna Berlicka

Michał J. Białek

Agata Białońska

Kamil Kupietz

Ewa Pacholska-Dudziak

Lechosław Latos-Grażyński

Rok wydania

2016

Czasopismo

Chemistry-A European Journal

Numer woluminu

22

Strony

7602-7608

DOI

10.1002/chem.201600606

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

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.

Słowa kluczowe

density functional calculations, macrocycles, phenanthrenes, porphyrinoids, sapphyr in

Adres publiczny

http://dx.doi.org/10.1002/chem.201600606

Strona internetowa wydawcy

onlinelibrary.wiley.com

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