Surface functionalization with carboxylic acids by photochemical microcontact printing and tetrazole chemistry

Christoph Buten, Sebastian Lamping, Martin Korsgen, Henrich F. Arlinghaus, Craig Jamieson, Bart Jan Ravoo

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

In this paper, we show that carboxylic acid-functionalized molecules can be patterned by photochemical microcontact printing on tetrazole-terminated self-assembled monolayers. Upon irradiation, tetrazoles eliminate nitrogen to form highly reactive nitrile imines, which can be ligated with several different nucleophiles, carboxylic acids being the most reactive. As a proof of concept, we immobilized trifluoroacetic acid to monitor the reaction with X-ray photoelectron spectroscopy. Moreover, we also immobilized peptides and fabricated carbohydrate−lectin as well as biotin−streptavidin microarrays using this method. Surface-patterning was demonstrated by fluorescence microscopy and time-of-flight secondary ion mass spectrometry
LanguageEnglish
Number of pages17
JournalLangmuir
Early online date16 Jan 2018
DOIs
Publication statusE-pub ahead of print - 16 Jan 2018

Fingerprint

tetrazoles
Carboxylic Acids
Carboxylic acids
carboxylic acids
printing
Printing
Tetrazoles
chemistry
Trifluoroacetic acid
Trifluoroacetic Acid
Nitriles
Nucleophiles
biotin
Imines
Streptavidin
Fluorescence microscopy
nucleophiles
nitriles
carbohydrates
Self assembled monolayers

Keywords

  • carboxylic acid
  • X-ray photoelectron spectroscopy
  • fluorescence microscopy

Cite this

Buten, Christoph ; Lamping, Sebastian ; Korsgen, Martin ; Arlinghaus, Henrich F. ; Jamieson, Craig ; Ravoo, Bart Jan. / Surface functionalization with carboxylic acids by photochemical microcontact printing and tetrazole chemistry. In: Langmuir. 2018.
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Surface functionalization with carboxylic acids by photochemical microcontact printing and tetrazole chemistry. / Buten, Christoph; Lamping, Sebastian; Korsgen, Martin; Arlinghaus, Henrich F.; Jamieson, Craig; Ravoo, Bart Jan.

In: Langmuir, 16.01.2018.

Research output: Contribution to journalArticle

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AU - Buten, Christoph

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AU - Jamieson, Craig

AU - Ravoo, Bart Jan

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AB - In this paper, we show that carboxylic acid-functionalized molecules can be patterned by photochemical microcontact printing on tetrazole-terminated self-assembled monolayers. Upon irradiation, tetrazoles eliminate nitrogen to form highly reactive nitrile imines, which can be ligated with several different nucleophiles, carboxylic acids being the most reactive. As a proof of concept, we immobilized trifluoroacetic acid to monitor the reaction with X-ray photoelectron spectroscopy. Moreover, we also immobilized peptides and fabricated carbohydrate−lectin as well as biotin−streptavidin microarrays using this method. Surface-patterning was demonstrated by fluorescence microscopy and time-of-flight secondary ion mass spectrometry

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