An essential feature of the living systems is their capacity to adapt to environmental pressure. Within a given species, natural selection is known to favor the variant, which is the most adapted to the external conditions. This strategy can be implemented to molecular systems to provide adaptative nano-objects and nano-materials that can mimic biological features (self-repair, selection of the best binder, self-replication, cooperativity…). By combining molecular building blocks of various functionalities and connect them with reversible linkages, the chemist can spontaneously generate a compositional and structural wealth of assembled architectures, the reversibility of their internal connections allowing evolutionary processes to occur under external physical or chemical stimuli. This dynamic combinatorial chemistry provides a straightforward access both to nano-objects and nano-materials adapting their composition and structure to optimize the interactions with molecular partners. Similarly to the immune system, such processes can lead to the spontaneous selection and amplification the nano-objects with the highest affinity for a biomolecular target, thereby yielding tailored molecular selectors and sensors. Similarly to protein assemblies, nano-materials capable of self-repair, stimulus-induced cooperative formation-dissociation and molecular imprinting can be obtained, paving the way toward ultraselective transportation, extraction and waste recycling devices.