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Template-stereocontrolled [2 + 2] photoreactions directed by surface recognition on hydrophilic functionalized carbon materials

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Abstract

Supramolecular assistance of the regioselective synthesis of single dimers from [2 + 2] photoreactions surface-directed by multivalent H-bonding exo-templates based on hydrophilic carbon materials (HCMs) is highlighted for the first time. Supramolecular photochemistry of stilbenes assisted by either functionalized carbon nanotubes or sub-microspheres afforded a single rtct-isomer after two consecutive steps in solution (UV-irradiation and hydrothermal isomerization). Carbon spheres display the ability to mediate the dimerization of 4-cinammic acid derivatives with moderate to quantitative yields. This result is obtained either in solution or via mechanochemical grinding assistance of carbon sphere/cinnamic derivative assemblies. The structure-templating features of such nanomaterials are discussed as a function of surface recognition processes due to the presence of –COOH and –OH groups on the surface and the effective carbon template : substrate ratio.

Graphical abstract: Template-stereocontrolled [2 + 2] photoreactions directed by surface recognition on hydrophilic functionalized carbon materials

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Publication details

The article was received on 10 Jun 2017, accepted on 25 Apr 2018 and first published on 03 May 2018


Article type: Paper
DOI: 10.1039/C7CE01090G
Citation: CrystEngComm, 2018, Advance Article
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    Template-stereocontrolled [2 + 2] photoreactions directed by surface recognition on hydrophilic functionalized carbon materials

    G. Ortega and A. Briceño, CrystEngComm, 2018, Advance Article , DOI: 10.1039/C7CE01090G

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