The Self-Assembly of a Lipophilic Guanosine Nucleoside into Polymeric Columnar Aggregates: The Nucleoside Structure Contains Sufficient Information To Drive the Process towards a Strikingly Regular Polymer

Amplification of Chirality in Dynamic Supramolecular Aggregates

“…In a similar approach, apolar lipophilic guanosine complexes were prepared and studied in apolar solvents. In the presence of alkali‐metal ions, these guanosine derivatives form polymeric tubular structures 108. Amplification of chirality was not studied in these aggregates.…”

“…Gottarelli and co‐workers evaluated the self‐assembly of guanosine derivatives into columnar aggregates in water as well as in apolar solvents 108. 114 The hierarchical self‐assembly of oligomeric deoxyguanosines in water through hydrogen bonding is initiated by the formation of cyclic tetramers, which stack into a columnar superstructure.…”

Dynamers at the Solid–Liquid Interface: Controlling the Reversible Assembly/Reassembly Process between Two Highly Ordered Supramolecular Guanine Motifs

“…The STM study of a monolayer of guanine solution containing 100 equivalents of potassium picrate revealed the formation of a G 4 ‐based architecture at the surface (Figure 1 b). 31, 32 The unit‐cell parameters, a =(1.6±0.2) nm and α =(90±3)°, lead to an area A =(2.56±0.45) nm 2 , where each unit cell contains four molecules of 1 and one potassium ion. The area occupied by a single molecule of 1 amounts to (0.64±0.1) nm 2 .…”

A lipophilic “fully-anti” dodecamer from a (5′S)-5′,8-cyclo-2′-deoxyguanosine

“…However, the signature of at least two G4s emerges by lowering temperature down to -30°C, when two sets of well separated resonances, corresponding to H-bonded and free amino protons, are observed ( Figure S7). [21,26] By combined COSY, HSQC, HMBC, 1D and 2D-NOE experiments performed at -20°C, the three sets of signals observed in the 1 H-NMR spectrum of D can be assigned to the three G4s (labeled ,  and Figure S8 and table S1) and a full structural characterization of D in solution is obtained (see SI for details). The two faces of a G4 are diastereotopic and usually are referred to as head (H) (clockwise motion on going from H-bond donors to acceptors) or tail (T) (counterclockwise motion) ( Figure S10).…”

“…[22] In hexadecamers both conformations can be present, but syn is the preferred one, [12] and the same holds for the pseudo-polymer. [21]…”