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Single-Molecule Orthogonal Double-Click Chemistry-Inorganic to Organic Nanostructure Transition.

Barry Arkles1, Jonathan Goff1, Taewoo Min1

  • 1Gelest, Inc., 11 Steel Road E, Morrisville, Pennsylvania 19067, United States.

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Summary
This summary is machine-generated.

Thiasilacyclopentane (TSCP) and azasilacyclopentane (ASCP) enable rapid surface functionalization through "simultaneous double-clicking." These reactions quickly modify inorganic surfaces, revealing groups for subsequent organic reactions.

Keywords:
Huisgen cycloadditionantiproliferative coatingdouble-click chemistryglass-strengtheningheteroatom silacyclopentanessurface modificationthiol−ene

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Surface Chemistry

Background:

  • Thiasilacyclopentane (TSCP) and azasilacyclopentane (ASCP) are cyclic compounds used for surface functionalization.
  • These reagents facilitate rapid inorganic click reactions on hydroxylated surfaces.

Purpose of the Study:

  • To explore the extension of TSCP and ASCP chemistry to
  • simultaneous double-clicking
  • reactions involving both inorganic and organic substrates.

Main Methods:

  • Investigated the use of TSCPs and ASCPs for simultaneous and tandem double-click reactions.
  • Characterized the rapid ring-opening click reaction on inorganic substrates (∼1 s at 30 °C).
  • Examined functionalized ASCPs (N-alkenyl-, N-aminoalkyl, N-alkynyl-ASCPs) for sequential functionalization.

Main Results:

  • Demonstrated successful "simultaneous double-clicking" where an initial inorganic click reaction reveals reactive groups (mercaptan or secondary amine) for a subsequent organic click reaction.
  • Showcased tandem double-click reactions, allowing for sequential functionalization by adding organic substrates after the inorganic click.
  • Confirmed that functionalized ASCPs can undergo reversible tandem double-click reactions, enabling control over the functionalization sequence.

Conclusions:

  • TSCPs and ASCPs offer versatile platforms for rapid, sequential surface functionalization through double-click mechanisms.
  • The ability to perform simultaneous or tandem double-clicking provides tunable strategies for modifying surfaces with inorganic and organic moieties.
  • Functionalized ASCPs introduce an additional layer of control, allowing for reversed functionalization sequences.