Non-disk-shaped molecules self-assembled to form columnar-type helical aggregates with gel ability through π-stacking interactions among the central tris(phenylethynylphenyl)adamantane moieties, hydrogen-bonding interactions among the alanine parts with amide groups, and van der Waals interactions among the alkyl groups in nonpolar n-alkanes. The structural analyses of fibrous architectures with helicity were examined by FTIR, UV-Vis, and circular dichroism (CD) spectroscopy and FE-SEM measurements. In contrast, the formation of fibrous structures was observed from adamantane-based tripodal molecules due to solvophobic interactions in polar EtOH, which showed no detectable Cotton effect in the CD measurement, indicating the induction of solvato-controlled helicity in the self-assembly process. Chirality 2011. © 2011 Wiley Periodicals, Inc.