Concept of strain buildup disassembly of synthetic supramolecular tubules and molecular design of the building blocks. (A) Disassembly of synthetic tubules by light. Hydrophobic interaction, π–π stacking, and shape recognition drives the spontaneous assembly of the stable building blocks into supramolecular tubules in water. Light-triggered trans-to-cis isomerization within the hydrophobic part causes shape changes and eventually disassembly of the tubular structure. (B) Chiral building block (1) incorporating (S)-stereocenters in its hydrophilic moiety and its achiral counterpart (2). Notably, the chirality of building blocks has been proven to influence equilibrium dynamics of supramolecular assemblies dramatically (40). Upon irradiation with UV light (λ = 365 nm), the building block undergoes trans-to-cis isomerization (not all possible conformations are displayed on this scheme). The trans/cis ratio at photostationary state is ∼30/70 (SI Appendix, Fig. S5). The reverse cis-to-trans switching can be realized thermally (with a half-life of ca. 12 h at 20 °C), or by irradiation with visible light (SI Appendix, Fig. S6).