Synthesis and Spectral Study of a New Family of 2,5-Diaryltriazoles Having Restricted Rotation of the 5-Aryl Substituent

Synthesis and Spectral Study of a New Family of 2,5-Diaryltriazoles Having Restricted Rotation of the 5-Aryl Substituent

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Efficient synthesis of 2,5-diaryl substituted 4-azido-1,2,3-triazoles by the reaction of sodium azide with dichlorosubstituted diazadienes was demonstrated.The optical properties of shipping the prepared azidotriazoles were studied to reveal a luminescence maximum in the 360−420 nm region.To improve the luminescence quantum yields a family of 4-azido-1,2,3-triazoles bearing ortho-propargyloxy substituents in the 5 position was prepared.

Subsequent intramolecular thermal cyclization permits to construct additional triazole fragment and obtain unique benzoxazocine derivatives condensed with two triazole Electrical rings.This new family of condensed heterocycles has a flattened heterocyclic system structure to provide more conjugation of the 5-aryl fragment with the triazole core.As a result, a new type of UV/“blue light-emitting” materials with better photophysical properties was obtained.