DOI: 10.1557/jmr.1989.0886. Monolayers of 11-trichlorosilylundecyl thioacetate: A system that promotes adhesion between silicon dioxide and evaporated gold

Monolayers of 11-trichlorosilylundecyl thioacetate: A system that promotes adhesion between silicon dioxide and evaporated gold

10.1557/jmr.1989.0886

Crossref journal-article

Springer Science and Business Media LLC

Journal of Materials Research (297)

Abstract

The use of sulfur-containing organic monolayer films improves adhesion between gold and silicon dioxide. The structures of these monolayers were analyzed using contact angle, ellipsometry, and XPS. The zone of adhesive failure was at or near the gold-monolayer interface.

Bibliography

Wasserman, S. R., Biebuyck, H., & Whitesides, G. M. (1989). Monolayers of 11-trichlorosilylundecyl thioacetate: A system that promotes adhesion between silicon dioxide and evaporated gold. Journal of Materials Research, 4(4), 886â892.

Authors 3

Stephen R. Wasserman (first)
Hans Biebuyck (additional)
George M. Whitesides (additional)

References 36 Referenced 68

29Since the monolayers prepared from HTS were longer than those created from 1, the Au/C ratio exaggerates the difference in the amount of gold left on these surfaces. Comparisons to the Si 2p signal, which underestimates this difference, indicate that at least six times as much gold was left on the thiol-terminated interface as on the methyl-terminated one.
10.1016/0368-2048(76)80015-1
21The thioacetate was subjected to acidic rather than basic hydrolysis since monolayers from alkyltrichlorosilanes are not stable in base.
10.1016/0040-6090(83)90557-6
{'key': 'S0884291400004775_ref034', 'first-page': '1', 'volume-title': 'Journal of Organometallic Chemistry Library 5: Organometallic Chemistry Reviews', 'author': 'Lukevics', 'year': '1977'} / Journal of Organometallic Chemistry Library 5: Organometallic Chemistry Reviews by Lukevics (1977)
10.1021/ja00351a063
10.1149/1.2129295
10.1116/1.572142
24 Wasserman S.R. , Whitesides G.M. , Tidswell I.M. , Ocko B. , Pershan P.S. , and Axe J. D. , J. Am. Chem. Soc. (in press).
14Stable bis(alkylthiolate) gold(I) salts (Au(SR)2 -) have been prepared by reaction of Au(I) dihalides with alkylthiolates. Bowmaker G. A. and Dobson B.C. , J. Chem. Soc., Dalton Trans., 267 (1981).
30The binding energy of the gold is referenced to an average of the C 1s, O 1s, and Si 2p signals.
22This range is not significant. Ellipsometric measurements for organic monolayers on silicon have a precision of ± 2 Å.
10.1021/ja00183a049
10.1021/ja00237a017
10.1088/0031-8949/1/5-6/020
{'key': 'S0884291400004775_ref003', 'volume': '48', 'year': '1983', 'journal-title': 'Japanese Patent'} / Japanese Patent (1983)
16 Allara D. L. and Nuzzo R. G. , U.S. Patent 4690715 (1987).
10.1063/1.1138605
{'key': 'S0884291400004775_ref002', 'first-page': '506', 'volume': '31', 'author': 'Muecke', 'year': '1977', 'journal-title': 'Metalloberfläche'} / Metalloberfläche by Muecke (1977)
{'key': 'S0884291400004775_ref001', 'first-page': '55', 'volume': '2', 'author': 'Upite', 'year': '1977', 'journal-title': 'Tezisy Dokl. Vses. Simp. Akt. Pverkhn. Tel'} / Tezisy Dokl. Vses. Simp. Akt. Pverkhn. Tel by Upite (1977)
10.1063/1.89516
10.1063/1.94705
10.6028/jres.067A.040
10.1016/0167-5087(82)90308-8
10.1163/156856187X00256
10.1021/ja00246a011
19Solutions of 1 were used within 48 h of preparation. While a rigorously dry atmosphere was not required, too high a water content in the atmo-sphere resulted in polymerization and precipitation of the starting silane.
20 Wasserman S.R. , Tao Y-T. , and Whitesides G.M. , Langmuir (in press).
10.1016/0021-9797(84)90452-1
{'key': 'S0884291400004775_ref025', 'first-page': 'F', 'volume-title': 'CRC Handbook of Chemistry and Physics', 'author': 'Weast', 'year': '1984'} / CRC Handbook of Chemistry and Physics by Weast (1984)
26 Bain C.D. , Biebuyck H. A. , and Whitesides G.M. , Langmuir (in press).
27We do not know whether this binding energy indicates the presence of a thiol or of a disulfide. The difference in the binding energies of the S 2p electrons in a thiol (163.3 eV) and a disulfide (163.0 eV) is small. Values for the S 2s electrons are expected to differ by similar amounts. The difference in these binding energies is similar to the errors in our reference peaks. See Refs. 13 and 26.
28Adhesive failure for the thiol-terminated monolayers occurred, on average, in ̃15% of the total area covered by the tape. On individual samples failure was found over 2-50% of the surface. For the thio-acetate-terminated monolayers, failure occurred only on 25% of the samples and removed gold from less than 1% of the area covered by the tape. We believe that this difference in failure rates probably reflects contamination of the thiol interface during the hydrolysis of the thioacetate group.
31The binding energy of the sulfur in the thiol-terminated mono-layer (228.4 eV) was between that of the sulfur in the thioacetate group (228.7 eV) and that of the sulfur in the thiol bound to the gold (228.0 eV). Uncertainties in the reference peaks were, however, almost as large as this shift.
10.1103/PhysRevLett.51.2310
10.1021/la00080a021

Dates

Type	When
Created	17 years, 11 months ago (Sept. 27, 2007, 5:36 a.m.)
Deposited	4 years, 6 months ago (Feb. 24, 2021, 4:26 p.m.)
Indexed	1 year, 2 months ago (June 20, 2024, 1:11 a.m.)
Issued	36 years ago (Aug. 1, 1989)
Published	36 years ago (Aug. 1, 1989)
Published Online	14 years, 6 months ago (Jan. 31, 2011)
Published Print	36 years ago (Aug. 1, 1989)

Funders 0

None

BibTeX

@article{Wasserman_1989, title={Monolayers of 11-trichlorosilylundecyl thioacetate: A system that promotes adhesion between silicon dioxide and evaporated gold}, volume={4}, ISSN={2044-5326}, url={http://dx.doi.org/10.1557/jmr.1989.0886}, DOI={10.1557/jmr.1989.0886}, number={4}, journal={Journal of Materials Research}, publisher={Springer Science and Business Media LLC}, author={Wasserman, Stephen R. and Biebuyck, Hans and Whitesides, George M.}, year={1989}, month=aug, pages={886–892} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        6,
        20
      ]
    ],
    "date-time": "2024-06-20T05:11:02Z",
    "timestamp": 1718860262118
  },
  "reference-count": 36,
  "publisher": "Springer Science and Business Media LLC",
  "issue": "4",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2011,
            1,
            31
          ]
        ],
        "date-time": "2011-01-31T00:00:00Z",
        "timestamp": 1296432000000
      },
      "content-version": "unspecified",
      "delay-in-days": 7853,
      "URL": "https://www.cambridge.org/core/terms"
    }
  ],
  "content-domain": {
    "domain": [
      "www.cambridge.org"
    ],
    "crossmark-restriction": true
  },
  "published-print": {
    "date-parts": [
      [
        1989,
        8
      ]
    ]
  },
  "abstract": "<jats:p>The use of sulfur-containing organic monolayer films improves adhesion between gold and silicon dioxide. The structures of these monolayers were analyzed using contact angle, ellipsometry, and XPS. The zone of adhesive failure was at or near the gold-monolayer interface.</jats:p>",
  "DOI": "10.1557/jmr.1989.0886",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2007,
        9,
        27
      ]
    ],
    "date-time": "2007-09-27T09:36:04Z",
    "timestamp": 1190885764000
  },
  "page": "886-892",
  "update-policy": "http://dx.doi.org/10.1017/policypage",
  "source": "Crossref",
  "is-referenced-by-count": 68,
  "title": "Monolayers of 11-trichlorosilylundecyl thioacetate: A system that promotes adhesion between silicon dioxide and evaporated gold",
  "prefix": "10.1557",
  "volume": "4",
  "author": [
    {
      "given": "Stephen R.",
      "family": "Wasserman",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Hans",
      "family": "Biebuyck",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "George M.",
      "family": "Whitesides",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "297",
  "published-online": {
    "date-parts": [
      [
        2011,
        1,
        31
      ]
    ]
  },
  "reference": [
    {
      "key": "S0884291400004775_ref029",
      "unstructured": "29Since the monolayers prepared from HTS were longer than those created from 1, the Au/C ratio exaggerates the difference in the amount of gold left on these surfaces. Comparisons to the Si 2p signal, which underestimates this difference, indicate that at least six times as much gold was left on the thiol-terminated interface as on the methyl-terminated one."
    },
    {
      "key": "S0884291400004775_ref036",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0368-2048(76)80015-1"
    },
    {
      "key": "S0884291400004775_ref021",
      "unstructured": "21The thioacetate was subjected to acidic rather than basic hydrolysis since monolayers from alkyltrichlorosilanes are not stable in base."
    },
    {
      "key": "S0884291400004775_ref006",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0040-6090(83)90557-6"
    },
    {
      "key": "S0884291400004775_ref034",
      "first-page": "1",
      "volume-title": "Journal of Organometallic Chemistry Library 5: Organometallic Chemistry Reviews",
      "author": "Lukevics",
      "year": "1977"
    },
    {
      "key": "S0884291400004775_ref009",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00351a063"
    },
    {
      "key": "S0884291400004775_ref018",
      "doi-asserted-by": "publisher",
      "DOI": "10.1149/1.2129295"
    },
    {
      "key": "S0884291400004775_ref015",
      "doi-asserted-by": "publisher",
      "DOI": "10.1116/1.572142"
    },
    {
      "key": "S0884291400004775_ref024",
      "unstructured": "24 Wasserman S.R. , Whitesides G.M. , Tidswell I.M. , Ocko B. , Pershan P.S. , and Axe J. D. , J. Am. Chem. Soc. (in press)."
    },
    {
      "key": "S0884291400004775_ref014",
      "unstructured": "14Stable bis(alkylthiolate) gold(I) salts (Au(SR)2 -) have been prepared by reaction of Au(I) dihalides with alkylthiolates. Bowmaker G. A. and Dobson B.C. , J. Chem. Soc., Dalton Trans., 267 (1981)."
    },
    {
      "key": "S0884291400004775_ref030",
      "unstructured": "30The binding energy of the gold is referenced to an average of the C 1s, O 1s, and Si 2p signals."
    },
    {
      "key": "S0884291400004775_ref022",
      "unstructured": "22This range is not significant. Ellipsometric measurements for organic monolayers on silicon have a precision of \u00b1 2 \u00c5."
    },
    {
      "key": "S0884291400004775_ref010",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00183a049"
    },
    {
      "key": "S0884291400004775_ref013",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00237a017"
    },
    {
      "key": "S0884291400004775_ref032",
      "doi-asserted-by": "publisher",
      "DOI": "10.1088/0031-8949/1/5-6/020"
    },
    {
      "key": "S0884291400004775_ref003",
      "volume": "48",
      "year": "1983",
      "journal-title": "Japanese Patent"
    },
    {
      "key": "S0884291400004775_ref016",
      "unstructured": "16 Allara D. L. and Nuzzo R. G. , U.S. Patent 4690715 (1987)."
    },
    {
      "key": "S0884291400004775_ref017",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1138605"
    },
    {
      "key": "S0884291400004775_ref002",
      "first-page": "506",
      "volume": "31",
      "author": "Muecke",
      "year": "1977",
      "journal-title": "Metalloberfl\u00e4che"
    },
    {
      "key": "S0884291400004775_ref001",
      "first-page": "55",
      "volume": "2",
      "author": "Upite",
      "year": "1977",
      "journal-title": "Tezisy Dokl. Vses. Simp. Akt. Pverkhn. Tel"
    },
    {
      "key": "S0884291400004775_ref004",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.89516"
    },
    {
      "key": "S0884291400004775_ref005",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.94705"
    },
    {
      "key": "S0884291400004775_ref035",
      "doi-asserted-by": "publisher",
      "DOI": "10.6028/jres.067A.040"
    },
    {
      "key": "S0884291400004775_ref007",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0167-5087(82)90308-8"
    },
    {
      "key": "S0884291400004775_ref008",
      "doi-asserted-by": "publisher",
      "DOI": "10.1163/156856187X00256"
    },
    {
      "key": "S0884291400004775_ref011",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00246a011"
    },
    {
      "key": "S0884291400004775_ref019",
      "unstructured": "19Solutions of 1 were used within 48 h of preparation. While a rigorously dry atmosphere was not required, too high a water content in the atmo-sphere resulted in polymerization and precipitation of the starting silane."
    },
    {
      "key": "S0884291400004775_ref020",
      "unstructured": "20 Wasserman S.R. , Tao Y-T. , and Whitesides G.M. , Langmuir (in press)."
    },
    {
      "key": "S0884291400004775_ref023",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0021-9797(84)90452-1"
    },
    {
      "key": "S0884291400004775_ref025",
      "first-page": "F",
      "volume-title": "CRC Handbook of Chemistry and Physics",
      "author": "Weast",
      "year": "1984"
    },
    {
      "key": "S0884291400004775_ref026",
      "unstructured": "26 Bain C.D. , Biebuyck H. A. , and Whitesides G.M. , Langmuir (in press)."
    },
    {
      "key": "S0884291400004775_ref027",
      "unstructured": "27We do not know whether this binding energy indicates the presence of a thiol or of a disulfide. The difference in the binding energies of the S 2p electrons in a thiol (163.3 eV) and a disulfide (163.0 eV) is small. Values for the S 2s electrons are expected to differ by similar amounts. The difference in these binding energies is similar to the errors in our reference peaks. See Refs. 13 and 26."
    },
    {
      "key": "S0884291400004775_ref028",
      "unstructured": "28Adhesive failure for the thiol-terminated monolayers occurred, on average, in \u030315% of the total area covered by the tape. On individual samples failure was found over 2-50% of the surface. For the thio-acetate-terminated monolayers, failure occurred only on 25% of the samples and removed gold from less than 1% of the area covered by the tape. We believe that this difference in failure rates probably reflects contamination of the thiol interface during the hydrolysis of the thioacetate group."
    },
    {
      "key": "S0884291400004775_ref031",
      "unstructured": "31The binding energy of the sulfur in the thiol-terminated mono-layer (228.4 eV) was between that of the sulfur in the thioacetate group (228.7 eV) and that of the sulfur in the thiol bound to the gold (228.0 eV). Uncertainties in the reference peaks were, however, almost as large as this shift."
    },
    {
      "key": "S0884291400004775_ref033",
      "doi-asserted-by": "publisher",
      "DOI": "10.1103/PhysRevLett.51.2310"
    },
    {
      "key": "S0884291400004775_ref012",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/la00080a021"
    }
  ],
  "container-title": "Journal of Materials Research",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://www.cambridge.org/core/services/aop-cambridge-core/content/view/S0884291400004775",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2021,
        2,
        24
      ]
    ],
    "date-time": "2021-02-24T21:26:37Z",
    "timestamp": 1614201997000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "http://link.springer.com/10.1557/JMR.1989.0886"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1989,
        8
      ]
    ]
  },
  "references-count": 36,
  "journal-issue": {
    "issue": "4",
    "published-print": {
      "date-parts": [
        [
          1989,
          8
        ]
      ]
    }
  },
  "alternative-id": [
    "S0884291400004775"
  ],
  "URL": "http://dx.doi.org/10.1557/JMR.1989.0886",
  "relation": {},
  "ISSN": [
    "0884-2914",
    "2044-5326"
  ],
  "subject": [],
  "container-title-short": "J. Mater. Res.",
  "published": {
    "date-parts": [
      [
        1989,
        8
      ]
    ]
  },
  "assertion": [
    {
      "value": "Copyright \u00a9 Materials Research Society 1989",
      "name": "license",
      "label": "License",
      "group": {
        "name": "copyright_and_licensing",
        "label": "Copyright and Licensing"
      }
    }
  ]
}