Functional Systems Derived from Nucleobase Self‐assembly

Abstract

Dynamic and reversible non‐covalent interactions endow synthetic systems and materials with smart adaptive functions that allow them to response to diverse stimuli, interact with external agents, or repair structural defects. Inspired by the outstanding performance and selectivity of DNA in living systems, scientists are increasingly employing Watson−Crick nucleobase pairing to control the structure and properties of self‐assembled materials. Two sets of complementary purine‐pyrimidine pairs (guanine:cytosine and adenine:thymine(uracil)) are available that provide selective and directional H‐bonding interactions, present multiple metal‐coordination sites, and exhibit rich redox chemistry. In this review, we highlight several recent examples that profit from these features and employ nucleobase interactions in functional systems and materials, covering the fields of energy/electron transfer, charge transport, adaptive nanoparticles, porous materials, macromolecule self‐assembly, or polymeric materials with adhesive or self‐healing ability.

Emerging low-molecular weight nucleopeptide-based hydrogels: state of the art, applications, challenges and perspectives

“…1B) or other structures ( e.g. , Hoogsteen or wobble base pairs, triplets, tetrads), they are ideal tools to construct a myriad of complex and responsive supramolecular systems, 33–38 including hydrogels. 39–42…”

“…[30][31][32] Thanks to their inherent abilities to self-assemble mainly via hydrogen bonds and/or π-stacking interactions forming canonical Watson-Crick base pairs (Fig. 1B) or other structures (e.g., Hoogsteen or wobble base pairs, triplets, tetrads), they are ideal tools to construct a myriad of complex and responsive supramolecular systems, [33][34][35][36][37][38] including hydrogels. [39][40][41][42] The incorporation of nucleobase(s) into peptide sequences can follow several strategies considering different derivatives, from the nucleobase alone to the biologically-relevant nucleosides or nucleotides (in their ribo-or deoxyribo-forms, see Fig.…”

Dinucleoside‐Based Macrocycles Displaying Unusually Large Chelate Cooperativities

“…Over the last 8 years, our research group has studied diverse nanostructured molecular systems self‐assembled through H‐bonding interactions, [14,15] including, among others, [61] (sub)phthalocyanine π‐conjugated materials, [62–67] G‐quadruplexes, [68–72] and other DNA nucleobase‐based systems [73–75] . Part of our efforts were in particular dedicated to establishing a versatile methodology to prepare macrocycles with a controlled size, shape and composition based on the H‐bonding Watson‐Crick interaction [76–81] …”

Nucleobases thin films deposited on nanostructured transparent conductive electrodes for optoelectronic applications

“…Taking into account the side chain engineering as a method to tailor the properties of organic compound, nucleobases represent an interesting type of functionality that may be used as an order-inducing motif 22 . Very recent studies have emphasised the possibly to create new materials with complex structure and new properties based on supramolecular self-assembled nucleobase systems using DNA technology and (bio)chemistry 23 . Other new contributions concern the synthesis of nucleobases in natural environment as a key point in the prebiotic chemical evolution 24 .…”