The self-assembly of lipophilic deoxyguanosine derivatives 1 and 2 has been studied in solution by NMR spectroscopy and ESI-MS (electrospray ionization mass spectrometry). NMR data show the existence of two types of self-assembled, ribbonlike structures (A and B), which are connected at the guanine moieties through two different H-bonded networks. The first species (A), which is stable in the solid state and characterised by cyclic NH(2)-O (6) and NH(1)-N(7) hydrogen bonds, is detected soon after dissolving the polycrystalline powder in rigorously anhydrous CDCl3. In solution it slowly undergoes a structural transition towards a thermo-dynamically stable ribbon characterised by NH(1)-O(6) and NH(2)-N(3) cyclic hydrogen bonds (B). On the other hand, at surfaces, self-assembled ribbon nano-structures have been grown from solutions of derivative 1 both on mica and at the graphite - solution interface. They have been investigated by means of tapping mode scanning force microscopy (SFM) and scanning tunnelling microscopy (STM), respectively. SFM revealed dry, micrometer-long nanoribbons with a molecular cross-section, while STM imaging at submolecular resolution indicates a molecular packing of type A, like the one detected in the solid state. This indicates that, upon adsorption at the solid - liquid interface, the guanosine moieties undergo a structural rearrangement from a B-type to an A-type ribbon.
Gottarelli G., Masiero S., Mezzina E., Pieraccini S., Rabe J.P., Samori P., et al. (2000). The self-assembly of lipophilic guanosine derivatives in solution and on solid surfaces. CHEMISTRY-A EUROPEAN JOURNAL, 6(17), 3242-3248 [10.1002/1521-3765(20000901)6:17<3242::AID-CHEM3242>3.0.CO;2-K].
The self-assembly of lipophilic guanosine derivatives in solution and on solid surfaces
Gottarelli G.;Masiero S.;Mezzina E.;Pieraccini S.;Spada G. P.
2000
Abstract
The self-assembly of lipophilic deoxyguanosine derivatives 1 and 2 has been studied in solution by NMR spectroscopy and ESI-MS (electrospray ionization mass spectrometry). NMR data show the existence of two types of self-assembled, ribbonlike structures (A and B), which are connected at the guanine moieties through two different H-bonded networks. The first species (A), which is stable in the solid state and characterised by cyclic NH(2)-O (6) and NH(1)-N(7) hydrogen bonds, is detected soon after dissolving the polycrystalline powder in rigorously anhydrous CDCl3. In solution it slowly undergoes a structural transition towards a thermo-dynamically stable ribbon characterised by NH(1)-O(6) and NH(2)-N(3) cyclic hydrogen bonds (B). On the other hand, at surfaces, self-assembled ribbon nano-structures have been grown from solutions of derivative 1 both on mica and at the graphite - solution interface. They have been investigated by means of tapping mode scanning force microscopy (SFM) and scanning tunnelling microscopy (STM), respectively. SFM revealed dry, micrometer-long nanoribbons with a molecular cross-section, while STM imaging at submolecular resolution indicates a molecular packing of type A, like the one detected in the solid state. This indicates that, upon adsorption at the solid - liquid interface, the guanosine moieties undergo a structural rearrangement from a B-type to an A-type ribbon.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
