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首页> 外文会议>Symposium on Quantum Confined Semiconductor Nanostructures Dec 2-5, 2002 Boston, Massachusetts, U.S.A. >Functionalization of Porous Silicon with Alkenes and Alkynes via Carbocation-Mediated Hydrosilylation
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Functionalization of Porous Silicon with Alkenes and Alkynes via Carbocation-Mediated Hydrosilylation

机译：通过碳正离子介导的氢化硅烷化作用将有机硅与烯烃和炔烃官能化

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摘要

Efforts to produce stable, derivatized porous silicon have yielded a number of chemical methods capable of functionalizing this interesting material with organic monolayers. Hydride-terminated porous silicon substrates react with alkenes and alkynes in the presence of dilute triphenylcarbenium salt solutions to respectively produce alkyl- and alkenyl-functionalized materials. Characterization by transmission FTIR and solid-state NMR suggests the formation of highly stable silicon-carbon bonds to yield covalently bound organic moieties. Porous silicon passivated in this fashion exhibits a greater resistance than that of the native material to chemical degradation, indicating that the organic functionalities may serve to sterically shield the nanocrystallites from nucleophiles. Hydrosilylation is proposed to proceed via hydride abstraction from the substrate followed by electrophilic attack by the subsequent species upon the alkene/alkyne, a mechanism previously hypothesized for the formation of stabilized β-silyl carbocations. The reaction is tolerant of a variety of substrate functional groups and native porous silicon surfaces but depends markedly upon the identity of the salt counteranion, among other solution parameters.
机译：生产稳定的衍生化多孔硅的努力已经产生了许多化学方法，能够用有机单层功能化这种有趣的材料。氢化物封端的多孔硅基质在稀三苯基碳鎓盐溶液的存在下与烯烃和炔烃反应，分别生产烷基和烯基官能化的材料。通过透射FTIR和固态NMR进行的表征表明，形成了高度稳定的硅碳键，以产生共价键合的有机基团。与天然材料相比，以这种方式钝化的多孔硅对化学降解的抵抗力更大，这表明有机官能团可能会在空间上使纳米微晶免受亲核试剂的影响。提出氢化硅烷化是通过从底物提取氢化物，然后随后的物质对烯烃/炔的亲电进攻而进行的，该机理先前被认为是形成稳定的β-甲硅烷基碳正离子的机理。该反应可耐受多种底物官能团和天然多孔硅表面，但在很大程度上取决于盐抗衡阴离子的身份以及其他溶液参数。

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