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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Published inEuropean 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
LanguageEnglish
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
Online AccessGet full text

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Abstract 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.
AbstractList 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.
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.
Author Tonkoglazova, Daria I.
Misharev, Alexander D.
Guchunov, Andrey S.
Gulevskaya, Anna V.
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  givenname: Andrey S.
  surname: Guchunov
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  organization: Southern Federal University
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  givenname: Alexander D.
  surname: Misharev
  fullname: Misharev, Alexander D.
  organization: St. Petersburg State University
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Issue 30
Keywords 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
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Snippet Novel azine‐helicene hybrids (pyridine‐, pyrazine‐ and quinoxaline‐fused along the central ring [5]helicenes) have been prepared in good overall yields through...
Novel azine-helicene hybrids (pyridine-, pyrazine- and quinoxaline-fused along the central ring [5]helicenes) have been prepared in good overall yields through...
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SubjectTerms Absorption spectra
Azine‐helicene hybrids
Chemistry
Chemistry, Organic
Electrochemistry
Helical structures
Nitrogen heterocycles
Physical Sciences
Quinoxalines
Science & Technology
Synthetic methods
Title Synthesis and Characterization of Azine‐[5]Helicene Hybrids
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