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The third orthogonal dynamic covalent bond.

Santiago Lascano1,2, Kang-Da Zhang1,2, Robin Wehlauch1,3

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Researchers achieved orthogonal dynamic covalent bonds using disulfide, hydrazone, and boronate ester exchanges. This breakthrough enables selective bond formation and modification in complex functional systems.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Polymer Science

Background:

  • Orthogonal dynamic covalent bonds are crucial for constructing adaptive and responsive functional systems.
  • Disulfide and hydrazone exchanges are known orthogonal reactions, but integrating boronate esters has been challenging due to their lability.
  • Previous attempts to incorporate boronate esters failed because they readily exchanged, particularly under hydrazone exchange conditions.

Purpose of the Study:

  • To identify stable boronate ester variants compatible with orthogonal dynamic covalent chemistry.
  • To develop selective conditions for the independent exchange of disulfide, hydrazone, and boronate ester bonds.
  • To demonstrate the utility of these orthogonal bonds in functional multicomponent systems.

Main Methods:

  • Screening of bioinspired catechols and phenylboronic acids to find robust boronate esters.
  • Utilizing Kool's 2-aminophenol catalysts to selectively accelerate hydrazone exchange.
  • Establishing distinct reaction conditions (acidic, basic) for selective disulfide, hydrazone, and boronate ester exchange.

Main Results:

  • Identification of the least labile boronate esters through screening of natural product-inspired catechols.
  • Demonstration of selective exchange for disulfide, hydrazone, and boronate ester bonds under different conditions.
  • Confirmation of orthogonality by successful hydrazone exchange in multicomponent surface architectures with intact boronate esters and disulfides.

Conclusions:

  • Achieved the first demonstration of three orthogonal dynamic covalent bonds: disulfide, hydrazone, and boronate ester.
  • Developed a robust method for selective bond manipulation in complex chemical systems.
  • Validated the compatibility of these orthogonal bonds in functional multicomponent surface architectures.