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Volumn 23, Issue 18, 2007, Pages 9320-9329

Functionalization of acetylene-terminated monolayers on Si(100) surfaces: A click chemistry approach

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CYCLOADDITION; GRAFTING (CHEMICAL); SILICON; SURFACE REACTIONS; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 34548529656     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la701035g     Document Type: Article
Times cited : (258)

References (117)
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    • Non-quantitative yields for eventual protection/activation procedures pose limitations when high-quality surface modification is pursued. The presence of unreacted N-hydroxysuccinimide esters, upon reaction with an intended nucleophile, is a general example Liu, G, Nguyen, Q. T, Chow, E, Böcking, T, Hibbert, D. B, Gooding, J. J. Electroanalysis 2006, 18, 1141-1151
    • Non-quantitative yields for eventual protection/activation procedures pose limitations when high-quality surface modification is pursued. The presence of unreacted N-hydroxysuccinimide esters, upon reaction with an intended nucleophile, is a general example (Liu, G.; Nguyen, Q. T.; Chow, E.; Böcking, T.; Hibbert, D. B.; Gooding, J. J. Electroanalysis 2006, 18, 1141-1151).
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    • For a comprehensive review on organometallic chemistry of silicon and germanium, see
    • For a comprehensive review on organometallic chemistry of silicon and germanium, see Buriak, J. M. Chem. Rev. 2002, 102, 1271-1308.
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    • For examples on the thermal, non-catalyzed hydrosilylation of 1-alkynes on Si(100)-H surfaces, see (a) Sieval, A. B.; Opitz, R.; Maas, H. P. A.; Schoeman, M. G.; Meijer, G.; Vergeldt, F. J.; Zuilhof, H.; Sudhölter, E. J. R. Langmuir 2000, 16, 10359-10368.
    • For examples on the thermal, non-catalyzed hydrosilylation of 1-alkynes on Si(100)-H surfaces, see (a) Sieval, A. B.; Opitz, R.; Maas, H. P. A.; Schoeman, M. G.; Meijer, G.; Vergeldt, F. J.; Zuilhof, H.; Sudhölter, E. J. R. Langmuir 2000, 16, 10359-10368.
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    • Compound 3 has previously been reported to promote Cu-catalyzed transformations and has been successfully used as a bidentate ligand in the coupling of imidazoles with arylboronic acids. (Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.)
    • Compound 3 has previously been reported to promote Cu-catalyzed transformations and has been successfully used as a bidentate ligand in the coupling of imidazoles with arylboronic acids. (Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892-7897.)
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    • Synthesis schemes for the preparation of compounds 2a and 2c are included in Supporting Information.
    • Synthesis schemes for the preparation of compounds 2a and 2c are included in Supporting Information.
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    • Coupling reaction of surface 1 with 1-azidobutane 2a to afford surface 2 was performed with the reaction vessel immersed in a water bath set to 25 °C.
    • Coupling reaction of surface 1 with 1-azidobutane 2a to afford surface 2 was performed with the reaction vessel immersed in a water bath set to 25 °C.
  • 85
    • 34548525588 scopus 로고    scopus 로고
    • XPS spectra were analysed using freeware software XPSpeak developed by Dr. Raymond Kwok. Department of Chemistry, The Chinese University of Hong Kong
    • XPS spectra were analysed using freeware software XPSpeak developed by Dr. Raymond Kwok. Department of Chemistry, The Chinese University of Hong Kong.
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    • A parallel approach to evaluate reaction yields relied on a comparison between XPS C 1s intensities (integrated area of the corresponding fitted function) ascribed to atoms in different environments. Given that good agreement was generally observed between the two approaches used to quantitate the immobilization of azide species, for clarity, results from only the N/C elemental analysis method are reported in the text.
    • A parallel approach to evaluate reaction yields relied on a comparison between XPS C 1s intensities (integrated area of the corresponding fitted function) ascribed to atoms in different environments. Given that good agreement was generally observed between the two approaches used to quantitate the immobilization of azide species, for clarity, results from only the N/C elemental analysis method are reported in the text.
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    • Semi-empirical MOPAC calculation (Chem3D Ultra).
    • Semi-empirical MOPAC calculation (Chem3D Ultra).
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    • -5 Å.
    • -5 Å.
  • 105
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    • The observed XPS spectral position for nitrogen-bonded carbons was found to be in good agreement with binding-energy values reported by Böcking et al. for analogous carbon atoms (∼286.4 eV).5
    • 5
  • 106
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    • 29 concerns existed regarding the possibility of an ipso (at the same) substitution reaction at the surfacial silylated olefin, the putative interfacial species, [(a) Cerofolini, G. F.; Galati, C.; Reina, S.; Renna, L. Semicond. Sci. Technol. 2003, 18, 423-429], eventually leading to the complete removal of the entire organic assembly. As a result of the ability of silicon atom to stabilize a positive charge in the beta position, the carbocation originated upon protonation of the double bond affords a weakened carbon-silicon bond that is rapidly cleaved by nucleophiles
    • 29 concerns existed regarding the possibility of an ipso ("at the same") substitution reaction at the surfacial silylated olefin, the putative interfacial species, [(a) Cerofolini, G. F.; Galati, C.; Reina, S.; Renna, L. Semicond. Sci. Technol. 2003, 18, 423-429], eventually leading to the complete removal of the entire organic assembly. As a result of the ability of silicon atom to stabilize a positive charge in the beta position, the carbocation originated upon protonation of the double bond affords a weakened carbon-silicon bond that is rapidly cleaved by nucleophiles
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    • Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry; Oxford University Press: New York, 2001; Chapter 47]. We thus evaluated the effect on exposure of surface 3 to 0.3 HCl, but no evidence of an ipso product (degraded monolayer) was found.
    • (b) Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry; Oxford University Press: New York, 2001; Chapter 47]. We thus evaluated the effect on exposure of surface 3 to 0.3 HCl, but no evidence of an ipso product (degraded monolayer) was found.
  • 109
    • 34548537604 scopus 로고    scopus 로고
    • x species as indicated by XPS Si 2p narrow scans. (Figure S3). This strongly supports the presence of a densely packed acetylene-terminated monolayer effectively passivating the silicon surface.
    • x species as indicated by XPS Si 2p narrow scans. (Figure S3). This strongly supports the presence of a densely packed acetylene-terminated monolayer effectively passivating the silicon surface.
  • 114
    • 34548533513 scopus 로고    scopus 로고
    • 565b
    • 565b
  • 116
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    • For examples of the preparation of 1,3-diynes through homocoupling reactions of terminal alkynes, see (a) Cameron, M. D, Bennett, G. E. J. Org. Chem. 1957, 22, 557-558
    • For examples of the preparation of 1,3-diynes through homocoupling reactions of terminal alkynes, see (a) Cameron, M. D.; Bennett, G. E. J. Org. Chem. 1957, 22, 557-558.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.