“Click” Chemistry by Microcontact Printing

Rożkiewicz, Dorota I.; Jańczewski, Dominik; Verboom, Willem; Ravoo, Bart Jan; Reinhoudt, David N.

doi:10.1002/anie.200601090

Cited by 187 publications

(117 citation statements)

References 37 publications

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“…[34] Reinhoudt and co-workers first treated bromo-terminated SAMs with NaN 3 , creating an azide-terminated monolayer. Next, octadecyne was printed onto the monolayer by using a poly(dimethylsiloxane) PDMS stamp.…”

Section: Role Of Click Chemistry In Surface Engineeringmentioning

confidence: 99%

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

2007

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The increasing need for materials with tightly controlled structures will continue to fuel the induction of synthetic organic concepts into materials science. One powerful example is the embracement of “click chemistry” by the materials science community. Because of their high selectivity, near‐perfect reliability, high yields, and exceptional tolerance towards a wide range of functional groups and reaction conditions click reactions have recently attracted increased attention, specifically for use in polymer synthesis as well as for the modification of surfaces and nanometer‐ and mesoscale structures. As outlined in this Review article, click chemistry, such as the CuI‐catalyzed Huisgen 1,3‐dipolar cycloaddition and the Diels–Alder reaction, presents a synthetic concept that lends itself superbly to the controlled preparation of multifunctional materials.

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Section: Role Of Click Chemistry In Surface Engineeringmentioning

confidence: 99%

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

2007

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“…The biospecific interactions mediated by ligand conjugated PEG brushes enables reductionistic analysis of the effects of biochemical cues found within complex in vivo tissue microenvironments on individual cell phenotypes. Furthermore, bio-orthogonal "click" chemistries can be used to facilitate directional immobilization of ligands so that they are presented in native conformations [4][5][6] . Thus, microscale spatial patterning of PEG brushes is a versatile tool to create designer in vitro niches to investigate cell signaling induced by immobilized biochemical cues 6,7 .…”

Section: Introductionmentioning

confidence: 99%

Fabricating Complex Culture Substrates Using Robotic Microcontact Printing (R-µCP) and Sequential Nucleophilic Substitution

Knight

Klann

McNulty

et al. 2014

JoVE

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In tissue engineering, it is desirable to exhibit spatial control of tissue morphology and cell fate in culture on the micron scale. Culture substrates presenting grafted poly(ethylene glycol) (PEG) brushes can be used to achieve this task by creating microscale, non-fouling and cell adhesion resistant regions as well as regions where cells participate in biospecific interactions with covalently tethered ligands. To engineer complex tissues using such substrates, it will be necessary to sequentially pattern multiple PEG brushes functionalized to confer differential bioactivities and aligned in microscale orientations that mimic in vivo niches. Microcontact printing (μCP) is a versatile technique to pattern such grafted PEG brushes, but manual μCP cannot be performed with microscale precision. Thus, we combined advanced robotics with soft-lithography techniques and emerging surface chemistry reactions to develop a robotic microcontact printing (R-μCP)-assisted method for fabricating culture substrates with complex, microscale, and highly ordered patterns of PEG brushes presenting orthogonal 'click' chemistries. Here, we describe in detail the workflow to manufacture such substrates. Video LinkThe video component of this article can be found at

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“…16 As a result, it has been widely applied in manȳ elds, including, biochemistry, 17 macromolecular chemistry 18 and surface chemistry. 19 In the area of self-assembled monolayer (SAM), there have been a few reports of click chemistry on gold, 20 silica 21 and glass 22 surfaces. In this paper, we report our work on functionalizing the surface of quartz with pyrene using click chemistry and the relationship between surface coverage and pyrene monomer/excimer formation upon photoexcitation.…”

Section: Introductionmentioning

confidence: 99%

Pyrene Emission From Monolayers "Clicked" Onto Quartz

Song

Gorelik

Hobley

et al. 2013

J. Mol. Eng. Mater.

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A series of quartz surfaces were modi¯ed with a series of crosslinkers and functional groups in order to obtain an azide-terminated monolayer, which was then used to immobilize pyrene onto the surface via alkyne-azide \click" chemistry. During the course of the immobilization, di®erent ratios of tert-butyl diphenyl chlorosilane were used to control the distribution and hence the photophysical properties of the pyrene on the surface. The preparative surface reactions and photophysical properties were investigated with contact angle, X-ray photoelectron spectroscopy, UV-visible absorption and emission spectroscopy. High surface coverage was achieved of just under 1molecule per nm 2 . At this coverage all emission from the pyrene was in the form of excimer emission. Excimer emission dominated at all surface coverages greater than 0.45 molecules per nm 2 . Below this coverage the monomer emission could also be observed. The conclusions that can be drawn are important for understanding the interactions of neighboring molecules in molecular monolayers. Our results suggest that at high surface coverage a substantial number of the pyrene molecules are already close enough to their neighbors that pairs of them can be directly excited to form excimer with no requirement for di®usion. This can be stated because the long wavelength end of the pyrene absorption and excitation spectra show a broad tail that is assigned to a charge transfer band resulting from an electron being directly transferred from a ground state pyrene to a neighboring pyrene molecule. Furthermore, absorption spectra shifts also indicate that the pyrene molecules undergo some interactions on the surface when they are closely packed.

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“Click” Chemistry by Microcontact Printing

Cited by 187 publications

References 37 publications

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

Fabricating Complex Culture Substrates Using Robotic Microcontact Printing (R-µCP) and Sequential Nucleophilic Substitution

Pyrene Emission From Monolayers "Clicked" Onto Quartz

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“Click” Chemistry by Microcontact Printing

Cited by 187 publications

References 37 publications

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

Fabricating Complex Culture Substrates Using Robotic Microcontact Printing (R-&#181;CP) and Sequential Nucleophilic Substitution

Pyrene Emission From Monolayers "Clicked" Onto Quartz

Contact Info

Product

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Fabricating Complex Culture Substrates Using Robotic Microcontact Printing (R-µCP) and Sequential Nucleophilic Substitution