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

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 eithe...

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Bibliographic Details
Published in:CrystEngComm 2018, Vol.20 (21), p.2932-2939
Main Authors: Ortega, Gabriela, Briceño, Alexander
Format: Article
Language:English
Subjects:
Carbon
Carbon nanotubes
Dimerization
Dimers
Isomerization
Microspheres
Nanomaterials
Photochemistry
Substrates
Ultraviolet radiation
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Summary: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.
ISSN:1466-8033
1466-8033
DOI:10.1039/C7CE01090G