Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring
Daria I. Tonkoglazova, Anna V. Gulevskaya, Konstantin A. Chistyakov, О. И. Аскалепова
Abstract
Novel carbazole-based [6]helicenes fused with an azine ring (pyridine, pyrazine or quinoxaline) have been prepared through a five-step synthetic sequence in good overall yields. 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 and fluorescence spectra of the helicenes were investigated and compared to that of the parent carbazole-based [6]helicene (7 H -phenanthro[3,4- c ]carbazole).
Topics & Concepts
AzineCarbazoleHeliceneChemistryMoietyPyrazineRing (chemistry)QuinoxalineFluorescenceCrystallographyPyridineAnnulationCombinatorial chemistryStereochemistryPhotochemistryMoleculeOrganic chemistryCatalysisQuantum mechanicsPhysicsSynthesis and Properties of Aromatic CompoundsPhotochromic and Fluorescence ChemistryDNA and Nucleic Acid Chemistry