Cátia Carvalho (UHU/UALG) Cucurbituril complexes in the gas phase Cátia Carvalho (UHU/UALG) José Paulo da Silva (UAlg) Uwe Pischel (UHU) RISE Meeting Faro, 13 Dezember 2010

What is a cucurbituril ? Synthetic family of macrocyclic and pumpkin-shaped compounds (composed of n methylene-bridged glycoluril units, with a central hydrophobic cavity and two identical carbonyl-laced portals) Vary in size (n = 5, 6, 7, 8 and 10) and are highly symmetrical and rigid

What is an inclusion complex ? Cucurbiturils form inclusion complexes with several cationic and neutral molecules supramolecular chemistry the process is a self-process (assembly of the molecules) N O + N O +

Consequences of the formation of complexes and their applications The guest is removed from the solution and is in a new environment. This allows for their uses as: Vehicles for drug delivery Containers for gas storage Deaggregators of dyes Light-driven molecular switches, sensors, and motors Containers for carrying out selective reactions …

Studied guests Aminas; putrescine

Mass spectrum of CB8 alone m/z 687 m/z 1351 m/z 2016 m/z relative abundance Na+ Na+ Na+ (1328 + 2x23)/ 2 = 687 (CB[8] + 2xNa)2+ 1328 + 23 = 1351 (CB[8] + Na)+ (3x1328 + 2x23)/ 2 = 2016 (3xCB[8] + 2xNa)2+

Mass spectrum of CB8 with a dicationic species (1328 + 214)/ 2 = 771 (CB[8] + Guest)2+

Mass spectrum of CB8 with a single charged species + m/z 935 Na+ n = 1 or 2 Na+ Na+ Na+ relative abundance m/z 783 Na+ m/z 1036 Na+ m/z 214 m/z 687 n = 1 or 2 m/z

m/z 935 is a trimer

How can we be so sure ? - 1 1 Na+ MS4 MS2 MS3 m/z 2016 m/z 1115 relative abundance

What’s next ? Octa acid 1728

Thank you