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This study provides insight into the creation of a simultaneously multifunctional surface formed by balancing two orthogonal functions; water repellency and enzyme catalysis. A partially fluorinated thiol is used to impart bulk hydrophobicity on the surface, and an <jats:italic>N<\/jats:italic>\u2010hydroxysuccinimide ester\u2010terminated thiol provides a specific anchoring sites for the covalent enzyme attachment. Different ratios of the two thiols are mixed together to form amphiphilic self\u2010assembled monolayers, which are characterized with polarization\u2010modulation infrared reflection\u2013absorption spectroscopy and contact angle goniometry. The enzyme activity is measured by a fluorescence assay. With the results collected here, specific surface compositions are identified at which the orthogonal functions of water repellency and enzyme catalysis are balanced and exist simultaneously. An understanding of how to effectively balance orthogonal functions at surfaces can be extended to a number of higher\u2010scale applications.<\/jats:p>","DOI":"10.1002\/chem.201601720","type":"journal-article","created":{"date-parts":[[2016,7,13]],"date-time":"2016-07-13T06:13:05Z","timestamp":1468390385000},"page":"12068-12073","source":"Crossref","is-referenced-by-count":7,"title":["A Multifunctional Surface That Simultaneously Balances Hydrophilic Enzyme Catalysis and Hydrophobic Water Repellency"],"prefix":"10.1002","volume":"22","author":[{"given":"Timothy J.","family":"Lawton","sequence":"first","affiliation":[{"name":"U.S. Army-Natick Soldier Research Development &amp; Engineering Center  15 General Greene Avenue Natick MA 01760 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joshua R.","family":"Uzarski","sequence":"additional","affiliation":[{"name":"U.S. Army-Natick Soldier Research Development &amp; Engineering Center  15 General Greene Avenue Natick MA 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