Photoinduced alkyne-azide click reactions
AssigneeThe Regents of the University of Colorado, a body corporate
InventorsChristopher Bowman, Brian A. Adzima, Christopher J. Kloxin
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Abstract
The present invention includes a composition comprising an alkyne-based substrate, an azide-based substrate, a Cu(II) salt and a photoinducible reducing agent. The present invention further includes a method of immobilizing a chemical structure in a given pattern onto a section of the surface of a solid substrate, using the photoinducible Cu(I)-catalyzed azide-alkyne cycloaddition Click reaction.
Claims11
A composition comprising an alkyne-based substrate, an azide-based substrate, at least one Cu(II) salt and at least one photoinducible reducing agent,
- wherein said alkyne-based substrate comprises at least one reactive alkynyl group,
- wherein said azide-based substrate comprises at least one reactive azide group, and
- wherein exposure of at least a portion of said composition to electromagnetic radiation promotes formation of Cu(I), which catalyzes cycloaddition of said at least one reactive alkynyl group and said at least one reactive azide group.
A method of preparing a compound of formula (I):
- said method comprising the steps of:
- (i) mixing a compound of formula (II):
- R—C≡C—H (II),
- a compound of formula (III):
- R1—N3 (III),
- at least one Cu(II) salt and at least one photoinducible reducing agent, to generate a first composition,
- wherein R and R1 are independently alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, substituted heteroalkenyl, aryl, substituted aryl, aryl-(C1-C3)alkyl, heterocyclyl, substituted heterocyclyl, heteroaryl, or substituted heteroaryl;
- and
- (ii) exposing at least a portion of said first composition to electromagnetic radiation, whereby said at least one Cu(II) salt is at least partiallty reduced to a Cu(I) species, which catalyzes cycloaddition of said compound of formula (II) with said compound of formula (III) to form said compound of formula (I).
Dependencies are inferred from the claim text.