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|Title:||Attachment of styrene and phenylacetylene on Si(111)-7×7: The influence of substitution groups on the reaction mechanism and formation of π-conjugated skeletons|
|Citation:||Tao, F., Wang, Z.H., Lai, Y.H., Xu, G.Q. (2003-06-04). Attachment of styrene and phenylacetylene on Si(111)-7×7: The influence of substitution groups on the reaction mechanism and formation of π-conjugated skeletons. Journal of the American Chemical Society 125 (22) : 6687-6696. ScholarBank@NUS Repository. https://doi.org/10.1021/ja0208759|
|Abstract:||The interactions of styrene and phenylacetylene and their isotope substitutions with a Si(111)7×7 surface have been studied as model systems to mechanistically understand the chemical binding of conjugated π-electron systems to di-radical-like silicon dangling bonds of the adjacent adatom-rest atom pair. Vibrational studies show that styrene mainly binds to the surface through a diradical reaction involving both the external C=C and its conjugated internal C=C of the phenyl ring with an adjacent adatom-rest atom pair, forming a 5-ethylidene-1,3-cyclohexadiene-like skeleton. On the other hand, phenylacetylene was shown to be covalently attached to Si(111)-7×7 through the external C≡C, forming a styrene-like conjugation system. These experimental results are consistent with density functional theory calculations. The different binding mechanisms for styrene and phenylacetylene clearly demonstrate that reaction channels for multifunctional organic molecules are strongly dependent on the chemical and physical properties of the functional groups. The resulting π-electron conjugation structures may possibly be employed as intermediates for further organic syntheses and fabrication of multilayer organic films on semiconductor surfaces.|
|Source Title:||Journal of the American Chemical Society|
|Appears in Collections:||Staff Publications|
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