论文标题

在UHV条件下制备的功能化Si(001)上基于溶液的炔烃耦合

Solution-based alkyne-azide coupling on functionalized Si(001) prepared under UHV conditions

论文作者

Glaser, T., Meinecke, J., Länger, C., Heep, J., Koert, U., Dürr, M.

论文摘要

有机双层在硅上的合成是通过在超高真空(UHV)条件下的表面功能化和基于溶液的点击化学结合来实现的。在UHV中以高度完美制备硅(001)表面,并通过从气相从化学选择性吸附乙基环丙基环戊链霉塞那。然后,通过铜催化的叠氮化股份咔嗒声在乙腈中耦合第二个有机层。将样品通过溶剂的蒸气相直接从UHV转移到反应物的溶液中,然后回到UHV,而无需与环境条件接触。通过UHV中的X射线光电子光谱法监测每个反应步骤; N 1S光谱清楚地表明,在所用的两个测试分子中,即甲基化的二苯甲酰氮和叠取代的pyrene的叠氮化物组的点击反应。在这两种情况下,对表面上的乙基环丙基环辛烷分子的最多50-60%反应。

Synthesis of organic bi-layers on silicon was realized by a combination of surface functionalization under ultra-high vacuum (UHV) conditions and solution-based click chemistry. The silicon (001) surface was prepared with a high degree of perfection in UHV and functionalized via chemoselective adsorption of ethinyl cyclopropyl cyclooctyne from the gas phase. A second organic layer was then coupled in acetonitrile via the copper-catalyzed alkyne azide click reaction. The samples were directly transferred from UHV via the vapour phase of the solvent into the solution of reactants and back to UHV without contact to ambient conditions. Each reaction step was monitored by means of X-ray photoelectron spectroscopy in UHV; the N 1s spectra clearly indicated the click reaction of the azide group in the two test molecules employed, i.e., methyl-subsituted benzylazide and azide substituted pyrene. In both cases, up to 50 - 60 % of the ethinyl cyclopropyl cyclooctyne molecules on the surface were reacted.

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