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Singly and Doubly Neo-Confused Smaragdyrins
Yutao Rao1, Wenjing Zhou1, Ling Xu1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine, Ministry of Educational of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha 410081 , P. R. China.
Journal of the American Chemical Society
|November 7, 2019
Summary
Researchers synthesized stable neo-confused smaragdyrin mutants and their free bases, revealing unique properties like regioselective diprotonation and oxygenation. These findings advance the study of expanded porphyrins.
Area of Science:
- Organic Chemistry
- Porphyrin Chemistry
- Supramolecular Chemistry
Background:
- Smaragdyrins are important but challenging expanded porphyrins.
- Previous synthesis of smaragdyrins was recently achieved.
- Neo-confused porphyrinoids offer unique electronic and structural properties.
Purpose of the Study:
- To synthesize novel singly and doubly neo-confused [22]smaragdyrin BF2-complexes.
- To obtain the corresponding neo-confused [22]smaragdyrin free bases.
- To investigate the characteristic properties and reactivity of these new compounds.
Main Methods:
- Nucleophilic substitution reactions between a dibromodipyrrin and N-confused tripyrranes.
- Demetalation using methanesulfonic acid to yield free bases.
- Oxygenation reactions and metalation/demetalation for further functionalization.
Main Results:
- Successful synthesis of stable singly and doubly neo-confused [22]smaragdyrin BF2-complexes.
- Isolation of air-sensitive neo-confused [22]smaragdyrin free bases.
- Observation of decreased diatropic ring current, regioselective diprotonation, and smooth oxygenation.
Conclusions:
- Stable neo-confused smaragdyrin mutants and their free bases were synthesized.
- These compounds exhibit unique properties including regioselective protonation and oxygenation.
- The study provides access to novel expanded porphyrinoids for further investigation.
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