Construction of self-assembled monolayer terminated with N-heterocyclic carbene–rhodium(I) complex moiety

Hara, Kenji; Iwahashi, Keiji; Takakusagi, Satoru; Uosaki, Kohei; Sawamura, Masaya

doi:10.1016/j.susc.2007.04.158

Cited by 14 publications

(7 citation statements)

References 36 publications

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“…Hara and co-workers reported the first example of a SAM supported Rh–NHC complex 627 by immobilization of an alkanethiolate terminated Rh–NHC complex onto a gold surface (Figure ). The synthesis of 627 was conducted by simply immersing a gold-coated plate into a THF solution of the Rh–NHC complex at room temperature for 20 h. In order to prepare the desired monolayer compound, a special structural design of the NHC moiety was pursued.…”

Section: Synthetic Strategies For the Immobilization Of N-heterocycli...mentioning

confidence: 99%

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

et al. 2017

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Over the course of the past 15 years the success story of N-heterocyclic carbene (NHC) compounds in organic, inorganic, and organometallic chemistry has been extended to another dimension. The immobilization of NHC compounds, undergoing continuous diversification, broadens their range of applications and leads to new solutions for challenges in catalytic and synthetic chemistry. This review intends to present a synthetic toolkit for the immobilization of NHC compounds, giving the reader an overview on synthetic techniques and strategies available in the literature. By individually summarizing and assessing the synthetic steps of the immobilization process, a comprehensive picture of the strategies and methodologies for the immobilization of NHC compounds is presented. Furthermore, the characterization of supported NHC compounds is discussed in detail in order to set up necessary criteria for an in-depth analysis of the immobilized derivatives. Finally, the catalytic applications of immobilized NHC compounds are briefly reviewed to illustrate the practical use of this technique for a broad variety of reaction types.

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Section: Synthetic Strategies For the Immobilization Of N-heterocycli...mentioning

confidence: 99%

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective

et al. 2017

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“…The first method involves the direct attachment of transition-metal complexes with suitable ligands, for example, thiol terminated ligands on gold surfaces. 15,16 The second method employs the reaction of transition-metal containing precursors with suitably prefunctionalized surfaces. [17][18][19][20] For the latter approach, bifunctional linkers such as para-cyanobenzylmercaptan (pCBM) are required.…”

Section: Introductionmentioning

confidence: 99%

Self-assembled monolayers of benzylmercaptan and para-cyanobenzylmercaptan on gold: surface infrared spectroscopic characterization

Rajalingam

Hallmann

Strunskus

et al. 2010

Phys. Chem. Chem. Phys.

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Self-assembled monolayers (SAMs) on gold substrates were prepared from benzylmercaptan (BM) and para-cyanobenzylmercaptan (pCBM), and the resulting surfaces were investigated using conventional infrared reflection-absorption spectroscopy (IRRAS) as well as polarization modulation infrared reflection-absorption spectroscopy (PM-IRRAS). IRRAS data are analyzed by comparison with transmission IR spectra and theoretical (DFT) simulations. The spectroscopic results indicate the presence of well-ordered monolayers of BM and pCBM with an orientation perpendicular to the surface. IRRAS and PM-IRRAS data are compared to each other and the respective merits of both methods are discussed.

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“…[1,2] However, attempts to utilize the SAMmodified gold surface to prepare catalysts for organic synthesis have not been fully established. [3][4][5][6] Herein, we report the modification of gold surfaces with a caged, compact trialkylphosphane (SMAP) [7] which bears an alkanethiolate pendant group. These surfaces ([Au]-SMAP, 1) were utilized in a chip form for rhodium-catalyzed dehydrogenative alcohol silylation.…”

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confidence: 99%