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Erica Giraldi1, Rosario Scopelliti1, Farzaneh Fadaei-Tirani1

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New molecular cages featuring arylboronate ester caps were synthesized using metal-templated reactions. These stable, functionalizable cages offer potential for advanced material applications.

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Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Arylboronate esters are valuable functional groups in organic synthesis and materials science.
  • Metal-templated synthesis offers a route to complex molecular architectures.
  • Developing stable and functionalizable molecular cages is a key goal in supramolecular chemistry.

Purpose of the Study:

  • To synthesize novel molecular cages capped with arylboronate esters.
  • To investigate the role of metal templates in cage formation and stability.
  • To explore the functionalization and postsynthetic modification of these molecular cages.

Main Methods:

  • Metal-templated polycondensation reactions.
  • Utilized tris(2-formylpyridine oxime) ligand and arylboronic acids.
  • Employed Zn(II), Fe(II), Co(II), and Mn(II) triflate/triflimide salts as templates.

Main Results:

  • Successfully synthesized molecular cages with arylboronate ester vertices.
  • Metal ions coordinated internally, enhancing the hydrolytic stability of boronate esters.
  • Introduced cyano or aldehyde functionalities via functionalized arylboronic acids.
  • Demonstrated postsynthetic modification of aldehyde groups through imine bond formation.

Conclusions:

  • Metal-templated synthesis provides access to stable arylboronate ester-capped molecular cages.
  • Internal metal coordination enhances the stability of the boronate ester linkages.
  • The cages are amenable to functionalization and postsynthetic modification, expanding their utility.