Unveiling Adenine H-bonded Hexads: Hierarchical Self-Assembly for Helical Columnar Functional Materials
Year: 2025
Type: article
Abstract: This manuscript reports on an unusual self-assembly of small adenine-based molecules leading to complex, functional systems. Molecules feature an adenine nucleobase substituted at the N9 position with a triarylamine unit through a flexible spacer. Hydrogen bonding interactions prompt the formation of unprecedented adenine hexameric rosettes, which organize in dimers and then into helical columnar assemblies exhibiting hexagonal columnar liquid crystal phases, even with nonchiral molecules. Theoretical calculations including geometry optimization and prediction of vibrational modes have provided essential insight into the configuration of hydrogen bonds between adenine units to form stable hexads, and experimental and simulated X-ray diffraction (XRD) patterns are consistent with the unique helical self-assembly. Furthermore, molecular design including chirality in the flexible spacer and triarylamine electron-donor units steers these nanostructured materials toward functionalities related to the control of supramolecular chirality and semiconductivity. This is confirmed by thin film circular dichroism measurements for chirality and the space charge-limited current method for hole transport.
Source: JACS Au
Authors: Alejandro Martínez-Bueno, Génesis M. Valencia-Vásconez, Roberto Termine, Attilio Golemme, Josu Ortega, César L. Folcia, José M. Granadino-Roldán, Amparo Navarro, Raquel Giménez, Teresa Sierra
Language: English
Subfield: Biomaterials
Field: Materials Science
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $3,500
Funders: Ministerio de Ciencia, Innovación y Universidades, Eusko Jaurlaritza, Ministero dell’Istruzione, dell’Università e della Ricerca, Consiglio Nazionale delle Ricerche, Universidad de Granada, Universidad de Zaragoza, Gobierno de Aragón, Junta de Andalucía, Consejo Superior de Investigaciones Científicas, European Regional Development Fund, Agencia Estatal de Investigación, European Social Fund
Awards: G103507813, G1090104742, G1105844351, G1132911488, G1175115578, G1270864721, G1540886192, G1610934229, G1622782223, G1694479240, G2019505627, G2262748287, G2334324494, G2500112760, G2593392798, G2799588417, G2983119422, G300979063, G3026515866, G3082032993, G3088689905, G3480869486, G3992134414, G410571670, G425668148, G4293424916, G451917667, G4526231891, G464105488, G491712853, G5043742294, G5080475149, G5209569390, G5539308778, G5635532810, G5903000213, G5967599077, G6690466257, G6825541365, G6905628614, G7084143925, G7085067018, G7434936867, Cristales Líquidos y polímeros, G766069702, G7805626310, G7863371703, G8028106313, G8033231456, G8497050386, G8931991127, G983705713
OpenAlex ID: W4411459642