A Benchtop Method for Appending Protic Functional Groups to N‐Heterocyclic Carbene Protected Gold Nanoparticles

作者: Joseph F. DeJesus , Lindy M. Sherman , Darius J. Yohannan , Jeffrey C. Becca , Shelby L. Strausser

DOI: 10.1002/ANIE.202001440

关键词: NanoparticleAqueous solutionNoble metalAmideSurface modificationLigandCombinatorial chemistryChemistryColloidal goldCarbene

摘要: The remarkable resilience of N-heterocyclic carbene (NHC) gold bonds has quickly made NHCs the ligand choice when functionalizing surfaces. Despite rapid progress using deposition from free or CO2 -protected NHCs, synthetic challenges hinder functionalization NHC surfaces with protic functional groups, such as alcohols and amines, particularly on larger nanoparticles. Here, we synthesize NHC-functionalized gold(I) complexes aqueous nanoparticles without need for additional reagents, enabling otherwise difficult groups to be appended carbene. NHC-Au bond allows multi-step post-synthetic modification. Beginning nitro-NHC, form an amine-NHC terminated surface, which further undergoes amide coupling carboxylic acids. simplicity this approach, its compatibility nanoparticle solutions, ability yield functionality, greatly expands potential noble metal

参考文章(50)
Olga Lyandres, Nilam C. Shah, Chanda Ranjit Yonzon, Joseph T. Walsh, Matthew R. Glucksberg, Richard P. Van Duyne, Real-time glucose sensing by surface-enhanced Raman spectroscopy in bovine plasma facilitated by a mixed decanethiol/mercaptohexanol partition layer. Analytical Chemistry. ,vol. 77, pp. 6134- 6139 ,(2005) , 10.1021/AC051357U
Cathleen M. Crudden, J. Hugh Horton, Iraklii I. Ebralidze, Olena V. Zenkina, Alastair B. McLean, Benedict Drevniok, Zhe She, Heinz-Bernhard Kraatz, Nicholas J. Mosey, Tomohiro Seki, Eric C. Keske, Joanna D. Leake, Alexander Rousina-Webb, Gang Wu, Ultra stable self-assembled monolayers of N-heterocyclic carbenes on gold Nature Chemistry. ,vol. 6, pp. 409- 414 ,(2014) , 10.1038/NCHEM.1891
Mong-Tung Lee, Chen-Chan Hsueh, Michael S. Freund, Gregory S. Ferguson, Air Oxidation of Self-Assembled Monolayers on Polycrystalline Gold: The Role of the Gold Substrate Langmuir. ,vol. 14, pp. 6419- 6423 ,(1998) , 10.1021/LA980724C
Xiaoqian Ren, Enzhong Tan, Xiufeng Lang, Tingting You, Li Jiang, Hongyan Zhang, Penggang Yin, Lin Guo, Observing reduction of 4-nitrobenzenthiol on gold nanoparticles in situ using surface-enhanced Raman spectroscopy. Physical Chemistry Chemical Physics. ,vol. 15, pp. 14196- 14201 ,(2013) , 10.1039/C3CP51385H
Eleanor C. Hurst, Karen Wilson, Ian J. S. Fairlamb, Victor Chechik, N-Heterocyclic carbene coated metal nanoparticles New Journal of Chemistry. ,vol. 33, pp. 1837- 1840 ,(2009) , 10.1039/B905559B
David J. Lavrich, Sean M. Wetterer, Steven L. Bernasek, Giacinto Scoles, Physisorption and Chemisorption of Alkanethiols and Alkyl Sulfides on Au(111) Journal of Physical Chemistry B. ,vol. 102, pp. 3456- 3465 ,(1998) , 10.1021/JP980047V
C. Passingham, P.J. Hendra, C. Hodges, H.A. Willis, The Raman spectra of some aromatic nitro compounds Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 47, pp. 1235- 1245 ,(1991) , 10.1016/0584-8539(91)80210-A