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Self-Assembled Monolayers of Long-Chain Hydroxamic Acids on the Native Oxides of Metalsl John P

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Self-Assembled Monolayers of Long-Chain Hydroxamic Acids on the Native Oxides of Metalsl John P copyrighto reebby the A-""i"""TflJili'""i ff#tfl1TYJh133t;j1p""-i..ion orthe copyright owner. 813 Self-Assembled Monolayers of Long-Chain Hydroxamic Acids on the Native Oxides of Metalsl John P. Folkers, Christopher B. Gorman, Paul E. Laibinis, Stefan Buchholz, and GeorgeM. Whitesides* Department of Chemistry, Haruard Uniuersity, Cambridge, Massachusetts02138 Ralph G. Nuzzo* Departments of Materials Science and Engineering and Chemistry, Uniuersity of lllinois, Urbana-Champaign, (Irbana, Illinois 61801 Receiued September 79, 1994e Long-chain alkanehydroxamic acids adsorb on the native oxides of metals and formed oriented self- assembled monolayers (SAMs). This study examined SAMs of hydroxamic acids on the native oxides of copper, silver, titanium, aluminum, zirconium, and iron. These SAMs were characterized usingwettability, X-ray photoelectron spectroscopy (XPS), and polarized infrared external reflectance spectroscopy (PIERS). Alkanehydroxamic acids give better monolayers than the corresponding alkanecarboxylic acids on certain basic metal oxides (especially copper(Il) oxide). On the native oxide of copper (which has an isoelectric point greater than the pK" of the hydroxamic acid), the ligand is bound to the surface predominantly as the hydroxamate. The strength of the interaction between copper oxide and the hydroxamate allows incorporation of polar tail groups into the monolayer. On acidic or neutral metal oxides (e.g.,TiO2), the predominant speciesbound to the surface is the hydroxamic acid. Alkanehvdroxamic acids on titanium dioxide bind relatively weakly but. nonetheless.form SAlts that are more stable than those from carboxylic acids (although not as stable as those from alkanephosphonicacids r. Introduction thoroughly studied.l; SAMs of alkanethiolates on gold and silver are generally the most useful in scientific properties We have examined the of self-assembled applications,l8because of their stability and becausethe (SAMs) monolayers obtained by the adsorption of long- specificity of coordination of the sulfur atom to the metal (general chain alkanehydroxamic acids formula CHs- allows polar groups containing oxygen and nitrogen to be (CHz),CONHOH) onto the native oxidesof freshly evapor- incorporated into the SAM.2'|1're ated frlms of copper, silver, titanium, aluminum, zir- Alkanethiols do not adsorb, however, to the surfaces of conium, and iron and have comparedthese SAMs to others many metal oxides.20Carboxylic acids and phosphonic commonly used with these substrates. We have used acidsadsorb, but the adsorptioncan be weak.7-16These wettability, X-ray photoelectronspectroscopy (XPS ), and polarized infrared externai reflectance spectroscopy . ('hen. Srrr'.1980. 102.92*98. Netzer L.; Sagiv, (PIERS)in characterizingthesemonolayers. We conclude 1983.105. 671- 676. Moaz,R.:Sae-tv, J.J.Colloid that monolayers of alkanehydroxamic acids (or their t00.165 496. R Tao.\'.-T.: Whitesrdes, G. M. Langmuir 1989, anions) are more stable than monolayersobtained by the S, : adsorption of carboxylic acids on all of the surfaces (especiallycopper oxide and silver oxide), but they are less stable than monolayers obtained by the adsorption of alkanethiols to copper or silver. Of the many systems available for the formation of self- assembledmonolayers, monolayers obtained by the chemi- sorption of alkanethiols onto gold and silver,2 amonolayers obtained by the hydrolysis and polymerization of alkyl D. Chem. Phys. Lett. 1990. 167. 198- trichlorosilanes onto hydrated surfaces,5'6and monolayers obtained by the adsorption of carboxylic acidsT-ls or phosphonicacidslG onto metal oxideshave been the most 8 Abstract published in Aduance ACS Abstrocls, January 15, 1995. (1) This research was supported in part by the Office of Naval Research and the Advanced Research Projects Agency (ARPA). XPS spectra were obtained using instrument facilities purchased under the ARPAruRI program and maintained by the Harvard University Materials Research Laboratory. S.B. acknowledges a grant from the Studienstiftung desdeutschen Volkes (BASF-Forschungsstipendium). R.G.N. acknowledgessupport from the National ScienceFoundation (cHE-930095). (2) Nuzzo,R. G.; Allara, D. L. J. Am. Chem.Soc. 1983,105,4481- 4483. Porter, M. D.; Bright, T. B.;Allara, D. L.; Chidsey,C. E. D. J. Am. Chem.Soc. 1987, 109, 3559-3568. Bain, C. D.;Troughton,E. B.; Tao, Y.-T.; Evall, J.; Whitesides,G. M.; Nuzzo, R. G. J. Am. Chem. Soc. 1989,111,321-335. (3) Walczak,M.M.;Chung, C.;Stole,S. M.;Widrig, C.A.;Porter, M. D. J. Am. Chem. Soc. 1991. 113.2370-2378. (4) Laibinis, P. E.; Whitesides,G. M.; Allara, D. L. ; Tao,Y.-T. ; Parikh, A.N.; Nuzzo, R. G. J. Am. Chem.Soc. 1991, 113,7152-7767. 07 43-74631951241I-0813$09.00/0@ 1995American Chemical Society 814 Langmuir, Vol. 11,No. 3, 1995 Folkers et al. systemsalso cannot be used to incorporate polar groups Scheme 1. Synthesis of Hydroxamic Acids into a monolayer.ll Phosphonic acids have large head groups and can be inconvenient to synthesize. (1) cH3(cH2)^coc,- ----_ cH'{cH2)^coN^.p We have examined hydroxamic acids as an alterna- "r*oP tive to carboxylicacids (3) for self-assembledmonolayers on the surfacesof metal oxidesbecause their complexation constantswith metal ions in aqueoussolution are several ooEDC * H2NoJ > Ho{CH2t,"CoNroJ ordersof magnitude larger than thoseofcarboxylic acids2l Ho{cH2}lscooH and becausethey have similar sizes. Synthesis of long- l-\ chain hydroxamic acids is also straightforward.22'23 Y H2,Pd R(CH2).CONHO--l ---+ R(CH2).CONHOH O O-'M R = CHs,OH tt - ' \ o F.r't # f-ot *Af.o ,Ao, ,Ad" HH was slmthesizedusing 1-ethyl-3-(3-(dimethylamino)pro- pyl)carbodiimide (EDC) to couple the benzyl-protected 1234 hydroxylamine to 16-hydroxyhexadecanoicacid.23 The same deprotection schemewas used for this compound. When complexedto a single metal ion in solution, the Preparation ofSubstrates andMonolayers. MetaV greater stability of complexQswith hydroxamate relative metal oxide substrates were prepared by electron-beam to those with carboxylate reflects the larger bite size of evaporationof 600-1000 A of the pure metal onto silicon the hydroxamate,which forms five-memberchelate rings wafers that had been precoatedwith 50 A of titanium as with metal ions(2t. Incontrast, carboxyiateforms either an adhesionpromoter. The sampleswere exposedto air strained.four-member chelate rings (4t or monodentate upon removal from the chamber. because we were species.rlr; We had hopedthat this differencein binding interested in studf ing the adsorptionof monolayersto constantsin solutionwould alsobe reflected in the strength the native oxidesof the metals. In this paper,instead of of binding of hydroxamic acids to the ions on the surface writing "metaVmetal oxide" for each reference to a of a metal oxide. In fact, although hydroxamic acids do substrate with a native oxide, we will refer to them simply form more stable monolayersthan carboxylicacids, they as the metal oxide. The oxidation states of the metal in seem to use only one oxygen atom for coordination. the native oxides are given in Table 1 and the Experi- Results mental Section. Solutions of alkanehydroxamic acids and other adsor- Synthesis of Hydroxamic Acids. The long-chain, bates were prepared in either isooctaneor ethanol and methyl-terminated hydroxamic acids were synthesized were not degassed.The nominal concentrationin eachof by reacting the corresponding acid chloride and O- the solutionswas 1 mM, although most of the hydroxamic benzylhydroxylamine,followed by removal of the benzyl acids were not soluble in isooctane to this extent. group by catalytic hydrogenation over palladium on carbon Substrates were left in solution for 1 to 2 days at room (Scheme 1).22The hvdroxvl-terminated hvdroxamic acid temperature. After removal from solution,the samples were rinsed with heptaneand ethanol and then dried in r 18r Applicationsof thiols on goldand silver: Chidsey,C. E. D. Science of nitrogen. r\\'oshrngton.D.Cl.r 1991. 251.9I9 922. Hickman, J. J.; Ofer, D.; a stream Laibinis.P. E.:\\'hitesides. G. !I.:Wrighton, M. S.Science(Washington. Contact Angles on Monolayers of Hydroxamic D.('., 1991.252. 688 691. Prime, K. L.; Whitesides,G. M. Science Acids. Table 1 summarizes advancing and receding r l|'osht rtgtLtrt.D.C ., 1991.252. 1164- 1167. Joyce,S. A. ; Houston,J. E.; contact anglesof rvater and hexadecaneon monolayers )Iichalske.T. A. App/. Pht's.Lett. 1992,60,lI75-7177. Kumar, A.; Biebuvck.H. A.: Abbott. N. L.; Whitesides,G. M. J. Am. Chem. Soc. obtainedby the adsorptionof octadecanehydroxamicacid, 1992.11J. 9188 9189. Abbott,N. L.; Folkers,J. P.;Whitesides,G. M. stearicacid, octadecanephosphonic acid, and 16-hydroxy- SciencerV'ashington, D.C.) 1992,258,1380-1382.Ross, C. B.; Sun, hexadecanehydroxamicacid on the six substratessurveyed L6pez,G. L.; Biebuyck, L.: Clrooks.R. *-1.Langmuir 1993,9,632-636. We also presentcontact angles for mono- H. A. : Frisbie. C. D. ; Whitesides,G. M. Science( Washington,D.C.) 1993, in this study. 260.647 619. Lopez,G. L.; Albers, M. W.; Schreiber,S. L.; Carrol, R. layers of octadecanethiolateon copper.silver, and gold W.:Peralta.E.: Whitesides, G. M. J.Am.Chem. Soc.1993, 115,5877- for comparison,and contact anglesfor surfacesobtained 5878. Kumar. A.; Whitesides,G. M. Appl. Phys. Lett. 1993, 63, 2002 after attempting adsorptionsof the hydroxamic acid onto 2004. t 19t Nuzzo,R. G.; Zegarski,B. R.; Dubois,L. H. J. Am. Chem. Soc. gold. For consistency,all of the data in Table 1 were taken 1987. 109, 733-740. duringthis study, although severalof thesesystems have r20r The exceptionsbeing copper oxide, silver oxide, and possibly been studied previously.'21; other soft metal oxides such as those on platinum, zinc, and lead. For studies on the removal the native oxidesfrom copper and silver using The presenceof a closest-packed,methyl-terminated alkanethiols,see ref 4 and Laibinis, P. E.; Whitesides,G.M. J. Am. monolayeris often indicated by an advancing contactangle -- oQ;2ti2s Chem.Soc. 1992, 114.9022-9028. of water (surface tension Tyv 72 mJlm2 at 25 t21 i E.; R.M. Stability Constants;Plenum Martell, A. Smith, Critical above110o, and an advancingcontactangle ofhexadecane Press: New York, 1977;Vol.
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