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- Title
Incorporation of a Phenanthrene Subunit into a Sapphyrin Framework: Synthesis of Expanded Aceneporphyrinoids.
- Authors
Szyszko, Bartosz; Małecki, Marcin; Berlicka, Anna; Białek, Michał J.; Białońska, Agata; Kupietz, Kamil; Pacholska‐Dudziak, Ewa; Latos‐Grażyński, Lechosław
- Abstract
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.
- Subjects
HYDROCARBONS; ORGANIC compounds; ALIPHATIC hydrocarbons; ALKYLATION; ALKYNES
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 22, p7602
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201600606