This article is cited in 8 papers

Communications

New non-symmetric azido-diacetylenic s-triazine monomer for polycycloaddition

A. O. Petrov, S. V. Karpov, G. V. Malkov, A. V. Shastin, E. R. Badamshina

Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

Abstract: An original synthesis of a new non-symmetric energetic ABB' type monomer, 2-azido-4-propargylamino-6- propargyloxy-s-triazine, with a total yield of 40% involves the sequential introduction of propargylamino, propargyloxy and azido groups into s-triazine. DFT investigation of azide- Cl alkyne cycloaddition mechanism at M06-2X/6-311++G(d,p) level of theory for this monomer predicts that the regioselectivity of polycycloaddition reaction should increase with the number of propargylamino groups in the monomer structure due to the stabilization of the transition state, leading to 1,5-triazole regioisomer.

Keywords: ABB' monomers, s-triazine, azides, alkynes, hyperbranched polymers, M06-2X/6-311++G(d p), calculated Gibbs free energy, 123-triazoles.

Language: English

DOI: 10.1016/j.mencom.2022.07.012

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