A deeper understanding of the intrinsic conformational properties of natural and unnatural amino acids and their oligomers, depending on the surrounding chemical environment (e.g. the solvent), is essential for the rational design of polypeptides. Through a bottom up approach is indeed possible to design molecules which will show interesting and new macroscopic properties. In this master thesis, 2-indolincarboxylic acid and its oligomers have been synthesized and studied, as mimetics of both the natural amino acids proline and phenylalanine. In order to understand how the presence of the aromatic ring affects proline conformational properties and cis/trans equilibrium and how the conformational restraint affects phenylalanine self-assembly properties, we performed a series of conformational studies. Through different spectroscopic techniques and computational methods, we aimed to characterize 2-indolincarboxylic acid using the N-acetyl methyl ester derivative, focusing our attention on the effect of the chemical environment