Item type:Thesis, Open Access

Synthese bifunktionaler Cyclooctine zur Schichtsynthese auf Silizium und ein Beitrag zur Synthese von Azapentacenen mit alternierendem Stickstoff-Substitutionsmuster

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Date

2021-10-04

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Philipps-Universität Marburg
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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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Dates
Created: 2021Issued: 2021-10-04Updated: 2021-10-04
DOI
https://doi.org/10.17192/z2021.0494
Faculty
Fachbereich Chemie
Publisher
Philipps-Universität Marburg
Language
ger
Data types
DoctoralThesis
Keywords
siliconSyntheseorganische Chemiesynthesissemi conductororganic chemistryHalbleiterSilizium
DDC-Numbers
540
License
https://rightsstatements.org/vocab/InC-NC/1.0/
URI
https://open.uni-marburg.de/handle/10.17192/z2021.0494
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Meinecke, Jannick: Synthese bifunktionaler Cyclooctine zur Schichtsynthese auf Silizium und ein Beitrag zur Synthese von Azapentacenen mit alternierendem Stickstoff-Substitutionsmuster. : Philipps-Universität Marburg 2021-10-04. DOI: https://doi.org/10.17192/z2021.0494.

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