article · Scientific Reports
A charge-transfer complex has been formed through the self-assembly of an electron acceptor and an electron donor in an aqueous medium. The molecules, based on naphthalene diimide and dialkoxynaphthalene, were specifically structured to balance electrostatic forces, pi-pi stacking, and van der Waals interactions. This molecular arrangement prevents standard crystallisation and instead drives the directional growth of three-dimensional, flower-like nanostructures. Comparative experiments using an alternative donor molecule with a mismatched structure confirmed that this specific geometric orientation is essential for charge transfer to occur. Electron microscopy verified the flower-shaped nanostructures, while spectroscopic and electrochemical measurements confirmed the formation of the complex and demonstrated photoinduced electron transfer that generates radical ion pairs.
Controlling how nanoscale components assemble allows scientists to govern the movement of electrical charges through organic materials. Demonstrating that precise molecular geometry dictates charge transfer in water provides fundamental guidance for designing custom self-assembling materials with controlled optical and electronic properties.
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A charge-transfer (CT) complex self-assembled from an electron acceptor (NDI-EA: naphthalene diimide with appended diamine) and an electron donor (DAN: phosphonic acid-appended dialkoxynapthalene) in aqueous medium. The aromatic core of the NDI and the structure of DAN1 were designed to optimize the dispersive interactions (π-π and van der Waals interactions) in the DAN1-NDI-EA self-assembly, while the amino groups of NDI also interact with the phosphonic acid of DAN1 via electrostatic forces. This arrangement prevented crystallization and favored the directional growth of 3D flower nanostructures. This molecular geometry that is necessary for charge transfer to occur was further evidenced by using a mismatching DAN2 structure. The flower-shaped assembly was visualized by scanning electron and transmission electron microscopy. The formation of the CT complex was determined by UV-vis and cyclic voltammetry and the photoinduced electron transfer to produce the radical ion pair was examined by femtosecond laser transient absorption spectroscopic measurements.
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DOI: 10.1038/s41598-017-15599-9
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