Heterogeneous Catalysis through Microcontact Printing

Angewandte Chemie International EditionVolume 47, Issue 51 p. 9927-9932 Communication Heterogeneous Catalysis through Microcontact Printing† Jason M. Spruell, Jason M. Spruell Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA), Fax: (+1) 847-491-1009 http://stoddart.northwestern.edu These authors have contributed equally to the research described in this Communication.Search for more papers by this authorBonnie A. Sheriff Dr., Bonnie A. Sheriff Dr. Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/ These authors have contributed equally to the research described in this Communication.Search for more papers by this authorDorota I. Rozkiewicz Dr., Dorota I. Rozkiewicz Dr. Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede (The Netherlands), Fax: (+31) 53-489-4645 These authors have contributed equally to the research described in this Communication.Search for more papers by this authorWilliam R. Dichtel Dr., William R. Dichtel Dr. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA), Fax: (+1) 847-491-1009 http://stoddart.northwestern.edu Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/Search for more papers by this authorRosemary D. Rohde, Rosemary D. Rohde Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/Search for more papers by this authorDavid N. Reinhoudt Prof., David N. Reinhoudt Prof. [email protected] Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede (The Netherlands), Fax: (+31) 53-489-4645Search for more papers by this authorJ. Fraser Stoddart Prof., J. Fraser Stoddart Prof. [email protected] Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA), Fax: (+1) 847-491-1009 http://stoddart.northwestern.eduSearch for more papers by this authorJames R. Heath Prof., James R. Heath Prof. [email protected] Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/Search for more papers by this author Jason M. Spruell, Jason M. Spruell Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA), Fax: (+1) 847-491-1009 http://stoddart.northwestern.edu These authors have contributed equally to the research described in this Communication.Search for more papers by this authorBonnie A. Sheriff Dr., Bonnie A. Sheriff Dr. Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/ These authors have contributed equally to the research described in this Communication.Search for more papers by this authorDorota I. Rozkiewicz Dr., Dorota I. Rozkiewicz Dr. Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede (The Netherlands), Fax: (+31) 53-489-4645 These authors have contributed equally to the research described in this Communication.Search for more papers by this authorWilliam R. Dichtel Dr., William R. Dichtel Dr. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA), Fax: (+1) 847-491-1009 http://stoddart.northwestern.edu Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/Search for more papers by this authorRosemary D. Rohde, Rosemary D. Rohde Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/Search for more papers by this authorDavid N. Reinhoudt Prof., David N. Reinhoudt Prof. [email protected] Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede (The Netherlands), Fax: (+31) 53-489-4645Search for more papers by this authorJ. Fraser Stoddart Prof., J. Fraser Stoddart Prof. [email protected] Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA), Fax: (+1) 847-491-1009 http://stoddart.northwestern.eduSearch for more papers by this authorJames R. Heath Prof., James R. Heath Prof. [email protected] Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125 (USA) http://www.its.caltech.edu/∼heathgrp/Search for more papers by this author First published: 04 December 2008 https://doi.org/10.1002/anie.200803480Citations: 51 † The research was supported by the Microelectronics Advanced Research Corporation (MARCO) and its Focus Center of Functional Engineered NanoArchitectonics (FENA) and Materials, Structures, and Devices (MSD) and by the NanoImpuls/NanoNed program of the Dutch Ministry of Economic Affairs (grant TTF6329). J.M.S. gratefully acknowledges the award of a Graduate Research Fellowship from the National Science Foundation (NSF). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Minting a Stamp: The preparation of copper metal-coated elastomeric stamps and their use in catalyzing the Cu-catalyzed azide–alkyne cycloaddition reaction heterogeneously through microcontact printing is described (see scheme). This StampCat process is compared to other conventional surface-functionalization techniques, including traditional microcontact printing and solution–surface-based reactions. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200803480_sm_miscellaneous_information.pdf629.5 KB miscellaneous information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aZ. H. Nie, E. Kumacheva, Nat. Mater. 2008, 7, 277; 1bJ. Nakanishi, T. Takarada, K. Yamaguchi, M. Maeda, Anal. Sci. 2008, 24, 67; 1cL. J. Guo, Adv. Mater. 2007, 19, 495; 1dX. D. Chen, S. Lenhert, M. Hirtz, N. Lu, H. Fuchs, L. F. Chi, Acc. Chem. Res. 2007, 40, 393; 1eJ. Henzie, J. E. Barton, C. L. Stender, T. W. Odom, Acc. Chem. Res. 2006, 39, 249. 2 2aA. S. Anderson, A. M. Dattelbaum, G. A. Montaño, D. 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Throughout the reaction, the azide moieties are depleted while excess of the alkyne molecules diffuse freely, presumably maintaining a constant concentration. While these concentration effects are difficult to mimic in traditional homogeneous reaction strategies, the decreased reagent degrees of freedom affecting the potential energy landscape for the surface reactions in comparison to solution reactions introduces additional significant differences. However, the flooding conditions in alkyne were adapted as a reasonably close representation of the concentration conditions at the surface. 23V. O. Rodionov, V. V. Fokin, M. G. Finn, Angew. Chem. 2005, 117, 2250; Angew. Chem. Int. Ed. 2005, 44, 2210. 24A kinetic plot similar to Figure 4 b showing the full reaction time for the Solution–Surface reaction is included in the Supporting Information. 25T. Tsoncheva, S. Vankova, D. Mehandjiev, Fuel 2003, 82, 755. 26J. Iijima, J.-W. Lim, S.-H. Hong, S. Suzuki, K. Mimura, M. Isshiki, Appl. Surf. Sci. 2006, 253, 2825. 27A freely diffusing particle will move about 1 micrometer in 1 millisecond. 28The resolution achieved using the Reagent-Stamping protocol was similar to that of traditional microcontact printing for spatially selective reactions (see refs. [8–10]). Citing Literature Volume47, Issue51December 8, 2008Pages 9927-9932 ReferencesRelatedInformation