Tunable Multifunctional Mesoporous Silica Microdots Arrays by Combination of Inkjet Printing, EISA, and Click Chemistry

A novel technique combining inkjet printing (IJP), evaporation-induced self-assembly (EISA), and click chemistry is implemented for elaborating mesoporous silica-based multifunctional microdots arrays. The microdots are in situ azide-functionalized with (3-azidopropyl)triethoxysilane (AzPTES). AzPTES is directly added to the initial sol before IJP and co-condenses with the silica precursor (TEOS) during the evaporation-induced self-assembly (EISA) of micelles on the substrate. After extracting the surfactants to release the porosity, model alkynes, namely propargyl alcohol, methyl pent-4-ynoate, ethynylferrocene, and N-propargyl-4-amino-1,8-naphthalimide, are grafted by the azide–alkyne CuAAC click reaction. The demonstration is established that the click reaction is nearly quantitative and occurs in the whole volume of the microdots attesting the accessibility of the azide groups. By integrating an alkyne-containing silylated precursor in a similar route, azide-containing functional groups are anchored i...

[1]  John D. Brennan,et al.  Tailoring Sol–Gel-Derived Silica Materials for Optical Biosensing , 2012 .

[2]  Brian Derby,et al.  Inkjet printing ceramics: from drops to solid , 2011 .

[3]  Kinam Park,et al.  A Glucose Sensor Fabricated by Piezoelectric Inkjet Printing of Conducting Polymers and Bienzymes , 2011, Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.

[4]  E. Rivera-Muñoz,et al.  Sol Gel-Derived SBA-16 Mesoporous Material , 2010, International journal of molecular sciences.

[5]  J. Baumard,et al.  Inkjet-Printing-Engineered Functional Microdot Arrays Made of Mesoporous Hybrid Organosilicas , 2010 .

[6]  T. Brown,et al.  Click chemistry with DNA. , 2010, Chemical Society reviews.

[7]  Capucine Sassoye,et al.  “Chimie douce”: A land of opportunities for the designed construction of functional inorganic and hybrid organic-inorganic nanomaterials , 2010, Comptes Rendus Chimie.

[8]  O. Wolfbeis,et al.  Clickable fluorophores for biological labeling--with or without copper. , 2009, Organic & biomolecular chemistry.

[9]  G. Arrachart,et al.  Silylated melamine and cyanuric acid as precursors for imprinted and hybrid silica materials with molecular recognition properties. , 2009, Chemistry.

[10]  Sayam Sen Gupta,et al.  “Clickable” SBA-15 mesoporous materials: synthesis, characterization and their reaction with alkynes , 2009 .

[11]  J. Nakazawa,et al.  Controlled loadings in a mesoporous material: click-on silica. , 2008, Journal of the American Chemical Society.

[12]  W. Binder,et al.  'Click' Chemistry in Polymer and Material Science: An Update , 2008 .

[13]  Paul Yager,et al.  Demonstration of multi-analyte patterning using piezoelectric inkjet printing of multiple layers. , 2008, Analytica chimica acta.

[14]  C. Laberty‐Robert,et al.  Design, Synthesis, and Properties of Inorganic and Hybrid Thin Films Having Periodically Organized Nanoporosity† , 2008 .

[15]  T. Chartier,et al.  Ink-Jet Printing of Ceramic Micro-Pillar Arrays , 2006 .

[16]  J. Baumard,et al.  Ink Jet Printing of Microdot Arrays of Mesostructured Silica , 2006 .

[17]  Thierry Gacoin,et al.  Mesoporous 3D-hexagonal organosilicate films: Post-synthesis grafting vs. direct synthesis , 2006 .

[18]  M. Wark,et al.  Functionalized mesoporous silica films as a matrix for anchoring electrochemically active guests. , 2005, Langmuir : the ACS journal of surfaces and colloids.

[19]  Gary M Nishioka,et al.  Protein damage in drop-on-demand printers. , 2004, Journal of the American Chemical Society.

[20]  Dimitra N. Stratis-Cullum,et al.  Investigation of microfabrication of biological sample arrays using piezoelectric and bubble-jet printing technologies , 2004 .

[21]  Galo J. A. A. Soler-Illia,et al.  Fundamentals of Mesostructuring Through Evaporation‐Induced Self‐Assembly , 2004 .

[22]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[23]  Morten Meldal,et al.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. , 2002, The Journal of organic chemistry.

[24]  E. W. Meijer,et al.  Hydrogen-Bonded Complexes of Diaminopyridines and Diaminotriazines: Opposite Effect of Acylation on Complex Stabilities. , 1996, The Journal of organic chemistry.

[25]  Xue-Long Sun,et al.  Carbohydrate and protein immobilization onto solid surfaces by sequential Diels-Alder and azide-alkyne cycloadditions. , 2006, Bioconjugate chemistry.

[26]  H. Trost,et al.  Ink-jet-deposited microspot arrays of DNA and other bioactive molecules. , 2001, Methods in molecular biology.