Synthesis and Characterization of Azine‐[5]Helicene Hybrids

• Published in: European journal of organic chemistry Vol. 2019; no. 30; pp. 4879 - 4890
• Main Authors: Gulevskaya, Anna V., Tonkoglazova, Daria I., Guchunov, Andrey S., Misharev, Alexander D.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 15.08.2019; Wiley Subscription Services, Inc
• Subjects: Absorption spectra; Azine‐helicene hybrids; Chemistry; Chemistry, Organic; Electrochemistry; Helical structures; Nitrogen heterocycles; Physical Sciences; Quinoxalines; Science & Technology; Synthetic methods; CIRCULARLY-POLARIZED LUMINESCENCE; Helical structures; ENANTIOSELECTIVE SYNTHESIS; HELICENE; OPTICAL-PROPERTIES; CRYSTAL-STRUCTURES; Azine-helicene hybrids; STEREOSELECTIVE SYNTHESES; PHOTOPHYSICAL PROPERTIES; ONE HUNDRED YEARS; EXCITED-STATE DYNAMICS; FACILE SYNTHESIS; Nitrogen heterocycles; Synthetic methods
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201900818

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.