Synthesis and Characterization of Azine‐[5]Helicene Hybrids

Novel azine‐helicene hybrids (pyridine‐, pyrazine‐ and quinoxaline‐fused along the central ring [5]helicenes) have been prepared in good overall yields through a five‐step synthetic sequence. Commercially available 2,3‐dihaloazines were used as starting materials. To discern the effect of merging an...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-08, Vol.2019 (30), p.4879-4890
Main Authors: Gulevskaya, Anna V., Tonkoglazova, Daria I., Guchunov, Andrey S., Misharev, Alexander D.
Format: Article
Language:English
Subjects:
Absorption spectra
Azine‐helicene hybrids
Electrochemistry
Helical structures
Nitrogen heterocycles
Quinoxalines
Synthetic methods
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Summary:Novel azine‐helicene hybrids (pyridine‐, pyrazine‐ and quinoxaline‐fused along the central ring [5]helicenes) have been prepared in good overall yields through a five‐step synthetic sequence. Commercially available 2,3‐dihaloazines were used as starting materials. To discern the effect of merging an azine moiety within a helical skeleton, the X‐ray structures, UV/Vis absorption spectra, cathodic and anodic electrochemistry of the helicene hybrids were investigated and compared to that of the parent [5]helicene. A systematic study on the synthesis and properties of novel azine‐[5]helicene hybrids is reported. To discern the effect of merging an azine moiety within a helical skeleton, the X‐ray structures, UV/Vis absorption spectra, and cathodic and anodic electrochemistry of the helicene hybrids were investigated and compared to that of the parent [5]helicene.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900818