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

Buten, Christoph and Lamping, Sebastian and Korsgen, Martin and Arlinghaus, Henrich F. and Jamieson, Craig and Ravoo, Bart Jan (2018) Surface functionalization with carboxylic acids by photochemical microcontact printing and tetrazole chemistry. Langmuir. ISSN 0743-7463

[img]
Preview
Text (Buten-etal-Langmuir-2018-Surface-functionalization-with-carboxylic-acids-by-photochemical-microcontact)
Buten_etal_Langmuir_2018_Surface_functionalization_with_carboxylic_acids_by_photochemical_microcontact.pdf
Accepted Author Manuscript

Download (1MB)| Preview

    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