Direkte UV‐induzierte Funktionalisierung oberflächengebundener Hydroxygruppen mithilfe von Thiol‐Alkohol‐Chemie

Li, Linxian; Li, Junsheng; Du, Xin; Welle, Alexander; Grunze, M.; Trapp, Oliver

doi:10.1002/ange.201310692

Cited by 7 publications

(2 citation statements)

References 57 publications

(17 reference statements)

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“…Levkin’s research is focused on the investigation of cell‐surface interactions and the development of biofunctional materials, as well as nanoparticles for drug‐ and gene‐delivery applications. He has reported in Angewandte Chemie on the UV‐initiated modification of surface hydroxy groups with thiol‐containing molecules 3…”

Section: Featured …︁mentioning

confidence: 99%

Alfred Stock Memorial Prize: W. Kaim / Nernst–Haber–Bodenstein Prize: Emad F. Aziz / Ewald Wicke Prize: P. Levkin / Elected to the Berlin–Brandenburg Academy of Sciences: M. Driess

2014

Angew Chem Int Ed

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Section: Featured …︁mentioning

confidence: 99%

Alfred Stock Memorial Prize: W. Kaim / Nernst–Haber–Bodenstein Prize: Emad F. Aziz / Ewald Wicke Prize: P. Levkin / Elected to the Berlin–Brandenburg Academy of Sciences: M. Driess

2014

Angew Chem Int Ed

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“…Seine Forschungsschwerpunkte sind die Untersuchung der Wechselwirkung zwischen Zellen und Oberflächen und die Entwicklung von biofunktionellen Materialien und Nanopartikeln für den Wirkstoff‐ und Gentransport. In der Angewandten Chemie hat er die UV‐vermittelte Modifizierung von Oberflächen‐Hydroxygruppen mit thiolhaltigen Molekülen beschrieben 3…”

Section: Vorgestellt …︁unclassified

Alfred‐Stock‐Gedächtnispreis: W. Kaim / Nernst‐Haber‐Bodenstein‐Preis: Emad F. Aziz / Ewald‐Wicke‐Preis: P. Levkin / In die Berlin‐Brandenburgische Akademie der Wissenschaften gewählt: M. Driess

2014

Angewandte Chemie

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UV‐Induced Tetrazole‐Thiol Reaction for Polymer Conjugation and Surface Functionalization

Feng

Yang

et al. 2015

Angewandte Chemie

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A UV-induced 1,3-dipolar nucleophilic addition of tetrazoles to thiols is described. Under UV irradiation the reaction proceeds rapidly at room temperature, with high yields, without a catalyst, and in both polar protic and aprotic solvents, including water. This UV-induced tetrazole-thiol reaction was successfully applied for synthesis of small molecules, protein modification, and rapid and facile polymer-polymer conjugation.The reaction has been also demonstrated for the formation of micropatterns by site-selective surface functionalization. Superhydrophobic-hydrophilic micropatterns were successfully created by sequential modifications of a tetrazole-modified porous polymer surface with hydrophobic and hydrophilic thiols. A biotin functionalized surface could be fabricated in aqueous solutions under long-wavelength UV irradiation.Ever since the first reported photoreaction of an organic compound, santonin, in 1834 by Trommsdorf, [1] the spatially and temporally controllable photochemistry has found diverse and widespread applications, [2] including surface functionalization to create patterned or gradient immobilization of various substrates.[3] Photo-induced click reactions have been actively investigated during the last decade in attempts to combine the benefits of click reactions with the excellent spatial and temporal controllability of photochemical processes.[4] UV-induced thiolene and thiol-yne reactions are the most known radical photoclick reactions.[5] Non-radical photoreactions have also attracted a lot of attention in recent years.[6] For instance, Lin et al, [7] introduced a photo-click 1,3-dipolar tetrazole-ene reaction based on Huisgen's studies. [8] The tetrazole-ene reaction presents several advantages: simplicity of implementation, fast reaction kinetics, high yields, it is catalyst free, yields inoffensive byproducts (N2) and, therefore, bio-compatible. This and other photo reactions have been implemented in many different applications such as dendrimers synthesis, [9] bioconjugation, [6b, 6d, 6e, 10] in situ bio-labeling, [6c, 11] hydrogels formation, [12] surface functionalization [13] etc. Nevertheless, the implementation of photo reactions in bio-applications is still limited, partly because unnatural functional groups have to be first introduced to a biomolecule. In addition, only a few photo reactions could be applied for polymer-polymer coupling and site-selective conjugation of biomolecules on surfaces. [13b, 14] Thus, despite a progress in the field of photo-induced reactions, there is a clear need for novel efficient photo reactions that are selective to different types of functionalities, compatible with polymerpolymer conjugation and bioapplications. 50 years ago Huisgen et al. reported that thiophenol could be added to the intermediate nitrilimine generated from decomposition of 2,5-diphenyltetrazole in boiling thiophenol. [8a, 8b] Photolytic decomposition of tetrazoles with release of nitrogen and nitrilimines was also described.[8c] In this work, we repo...

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Direkte UV‐induzierte Funktionalisierung oberflächengebundener Hydroxygruppen mithilfe von Thiol‐Alkohol‐Chemie

Cited by 7 publications

References 57 publications

Alfred Stock Memorial Prize: W. Kaim / Nernst–Haber–Bodenstein Prize: Emad F. Aziz / Ewald Wicke Prize: P. Levkin / Elected to the Berlin–Brandenburg Academy of Sciences: M. Driess

Alfred Stock Memorial Prize: W. Kaim / Nernst–Haber–Bodenstein Prize: Emad F. Aziz / Ewald Wicke Prize: P. Levkin / Elected to the Berlin–Brandenburg Academy of Sciences: M. Driess

Alfred‐Stock‐Gedächtnispreis: W. Kaim / Nernst‐Haber‐Bodenstein‐Preis: Emad F. Aziz / Ewald‐Wicke‐Preis: P. Levkin / In die Berlin‐Brandenburgische Akademie der Wissenschaften gewählt: M. Driess

UV‐Induced Tetrazole‐Thiol Reaction for Polymer Conjugation and Surface Functionalization

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