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Synfacts 2011(3): 0265-0265  
DOI: 10.1055/s-0030-1259435
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

‘Hard-Core’ Diels-Alder

Contributor(s):Timothy M. Swager, Shuang Liu
G. Jarre, Y. Liang, P. Betz, D. Lang, A. Krueger*
Julius-Maximilians-Universität, Würzburg, Germany
Playing the Surface Game - Diels-Alder Reactions on Diamond Nanoparticles
Chem. Commun.  2011,  47:  544-546  
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Publication History

Publication Date:
16 February 2011 (online)

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Key words

diamond nanoparticles - Diels-Alder reaction - electrophilic aromatic substitution

Significance

A Diels-Alder reaction is used for the first time to functionalize the surface of diamond nanoparticles. Direct C-C coupling is achieved by reacting o-quinodimethanes with π-bonds on the surface of thermally annealed nanodiamond. Increasing the annealing temperature and introducing electron-withdrawing groups to the diene both lead to higher surface loading.

Comment

This method offers facile modification of surface properties of nanodiamond. The aryl­ated particles are very stable and can be further decorated by electrophilic aromatic substitution. For instance, 4-carboxy-o-quinodimethane-functionalized particles 2b are soluble in water and PBS buffer, while Oregon Green tagged conjugate 5 can be purified by conventional column chromatography.

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