Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 8651-8663 |
| Journal | Langmuir |
| Volume | 28 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 2012 |
Fingerprint
Keywords
- self-assembled monolayers
- terminated monolayers
- organic monolayers
- one-step
- functionalization
- chemistry
- films
- immobilization
- microarrays
- dna
Cite this
}
Copper-Free Click Biofunctionalization of Silicon Nitride Surfaces via Strain-Promoted Alkyne-Azide Cycloaddition Reactions. / Manova, R.K.; Pujari, S.P.; Weijers, C.A.G.M.; Zuilhof, H.; van Beek, T.A.
In: Langmuir, Vol. 28, No. 23, 2012, p. 8651-8663.Research output: Contribution to journal › Article › Academic › peer-review
TY - JOUR
T1 - Copper-Free Click Biofunctionalization of Silicon Nitride Surfaces via Strain-Promoted Alkyne-Azide Cycloaddition Reactions
AU - Manova, R.K.
AU - Pujari, S.P.
AU - Weijers, C.A.G.M.
AU - Zuilhof, H.
AU - van Beek, T.A.
PY - 2012
Y1 - 2012
N2 - Cu-free "click" chemistry is explored on silicon nitride (Si3N4) surfaces as an effective way for oriented immobilization of biomolecules. An omega-unsaturated ester was grafted onto Si3N4 using UV irradiation. Hydrolysis followed by carbodiimide-mediated activation yielded surface-bound active succinimidyl and pentafluorophenyl ester groups. These reactive surfaces were employed for the attachment of bicyclononyne with an amine spacer, which subsequently enabled room temperature strain-promoted azide alkyne cycloaddition (SPAAC). This stepwise approach was characterized by means of static water contact angle, X-ray photoelectron spectroscopy, and fluorescence microscopy. The surface-bound SPAAC reaction was studied with both a fluorine-tagged azide and an azide-linked lactose, yielding hydrophobic and bioactive surfaces for which the presence of trace amounts of Cu ions would have been problematic. Additionally, patterning of the Si3N4 surface using this metal-free click reaction with a fluorescent azide is shown. These results demonstrate the ability of the SPAAC as a generic tool for anchoring complex molecules onto a surface under extremely mild, namely ambient and metal-free, conditions in a clean and relatively fast manner.
AB - Cu-free "click" chemistry is explored on silicon nitride (Si3N4) surfaces as an effective way for oriented immobilization of biomolecules. An omega-unsaturated ester was grafted onto Si3N4 using UV irradiation. Hydrolysis followed by carbodiimide-mediated activation yielded surface-bound active succinimidyl and pentafluorophenyl ester groups. These reactive surfaces were employed for the attachment of bicyclononyne with an amine spacer, which subsequently enabled room temperature strain-promoted azide alkyne cycloaddition (SPAAC). This stepwise approach was characterized by means of static water contact angle, X-ray photoelectron spectroscopy, and fluorescence microscopy. The surface-bound SPAAC reaction was studied with both a fluorine-tagged azide and an azide-linked lactose, yielding hydrophobic and bioactive surfaces for which the presence of trace amounts of Cu ions would have been problematic. Additionally, patterning of the Si3N4 surface using this metal-free click reaction with a fluorescent azide is shown. These results demonstrate the ability of the SPAAC as a generic tool for anchoring complex molecules onto a surface under extremely mild, namely ambient and metal-free, conditions in a clean and relatively fast manner.
KW - self-assembled monolayers
KW - terminated monolayers
KW - organic monolayers
KW - one-step
KW - functionalization
KW - chemistry
KW - films
KW - immobilization
KW - microarrays
KW - dna
U2 - 10.1021/la300921e
DO - 10.1021/la300921e
M3 - Article
VL - 28
SP - 8651
EP - 8663
JO - Langmuir
JF - Langmuir
SN - 0743-7463
IS - 23
ER -