Synthese bifunktionaler Cyclooctine zur Schichtsynthese auf Silizium und ein Beitrag zur Synthese von Azapentacenen mit alternierendem Stickstoff-Substitutionsmuster
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Philipps-Universität Marburg
Abstract
By employing a bifunctional, strained cyclooctyne and an azide-incorporated tetrazine an
additive-free, sequential layer-by-layer synthesis was demonstrated. The conversion
was selective, fast, high-yielding and running at room temperature. The ligation steps in means of
SpAAC and IEDDA were first exhibited on a cholic acid derived triazide.Subsequently the
synthesis was examined on silicon(001) in cooperation with AG DÜRR. After the selective [2+2]-
reaction of the strained triple bond with silicon dimers, a tetrazine reacted within IEDDA to the
corresponding pyridazine and a second layer was built for the first time in UHV.
Since in a previous work a terminal alkyne did not react in UHV within a 1,3-dipolar
cycloaddition, a new strategy in order to synthesize a second layer for this bifunctional
cyclooctyne was established. By diving the organic-semiconductor interface into a
stain solution of azide and CuX(PPh3)3 (X = Br,I) in acetonitrile, a second layer was
successfully achieved in cooperation with AG DÜRR. To facilitate the reaction, suitable
conditions were investigated on a test system with particular requirements.
In addition to enol ether and bisalkyne different cyclooctynes and 8-membered-ring-vinyl
bromides were investigated towards their applicability for an additive-free layer-by-layer synthesis.
SuFEx, hydrazone-formation, esterification and 1,3-dipolar cycloaddition were inferior to
SpAAC & IEDDA.
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This item has been published with the following license: In Copyright