Synthesis of Verdazyl Radicals with Different Number of Methylene Fragments in the Internal Conjugated Diyne Moiety and Their Ability to Solid-State Polymerization

Abstract

Verdazyl radicals have been obtained from non-symmetric alkadiynyl ethers ofp-hydroxybenzaldehyde. Using these radicals, the effect of the distance between the conjugated diyne fragment and the bulky tetrazinyl substituent on the ability to solid-state polymerization under UV irradiation has been studied. It has been shown that the rate of solid-state polymerization (accompanied by the preservation of the radical site) is increased with an increase in the number of methylene groups in the alkadiyne fragment.

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Scheme
Scheme
Fig. 1.
Fig. 2.
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Notes

  1. 1.

    Cherry coloration of formazans 4a, 4b disappeared during 15 min, and the mixture became clay-colored.

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Correspondence to S. G. Kostryukov.

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Kostryukov, S.G., Pryanichnikova, M.K., Kozlov, A.S. et al. Synthesis of Verdazyl Radicals with Different Number of Methylene Fragments in the Internal Conjugated Diyne Moiety and Their Ability to Solid-State Polymerization. Russ J Gen Chem 90, 832–838 (2020). https://doi.org/10.1134/S1070363220050126

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Keywords:

  • verdazyl
  • tetrazinyl
  • leuco base
  • hydrazone
  • formazan
  • non-symmetric alkadiyne
  • solid-phase polymerization