1. 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

2. 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

3. 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 +

4. 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 …

5. Studied guests
Aminas; putrescine

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

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

8. 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

9. m/z 935 is a trimer

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

11. What’s next ?
Octa acid
1728

12. Thank you