![]() ![]() ![]() These factors are determined, however, by (i) the relative orientations, (ii) the intermolecular distances, and (iii) the energy matches involving neighboring redox-active units. The efficiency of intra- as well as intermolecular charge mobilities in organic semiconductors relies (6) on maximizing electronic coupling and minimizing reorganizational energies associated with charge transport between neighboring π-conjugated redox-active units. Understanding of the geometrical constraints between multiple redox-active aromatic building blocks that exhibit efficient electron hopping and delocalization has presented a considerable challenge to those researchers fabricating (1-5) organic photovoltaic and molecular electronic devices. #TRIANGLE ISOSCELES SERIES#The evaluation of the structure–performance relationships of this series of diimide-based triangles reveals that the increase in the number of NDI subunits, replacing PMDI ones, within the molecules improves the electrochemical cell performance of the batteries. The isosceles triangles have been employed as electrode-active materials in organic rechargeable lithium-ion batteries. Continuous-wave electron paramagnetic resonance and electron–nuclear double-resonance spectroscopic investigations, supported by density functional theory calculations, on the single-electron reduced radical anions of the isosceles triangles confirm the selective sharing of unpaired electrons among adjacent redox-active NDI subunit(s) within both molecules. Cyclic voltammetry reveals that both isosceles triangles can accept reversibly up to six electrons. The rigid isosceles triangle, composed of one NDI and two PMDI subunits, forms-in the presence of N,N-dimethylformamide-two different types of intermolecular NDI–NDI and NDI–PMDI π–π stacked dimers with opposite helicities in the solid state. Unlike previously investigated equilateral triangle containing three identical NDI subunits, both isosceles triangles do not choose to form one-dimensional supramolecular nanotubes by dint of interaction-driven columnar stacking. Single-crystal X-ray diffraction analyses reveal their rigid triangular prism-like geometries. 1H and 13C NMR spectroscopic investigations in solution confirm the lower symmetry ( C 2 point group) associated with these two isosceles triangles. ![]() Herein, we report on the synthesis, characterization, and application of two rigid chiral triangles, each of which consist of non-identical pyromellitic diimide (PMDI) and naphthalene diimide (NDI)-based redox-active units. Designing small-molecule organic redox-active materials, with potential applications in energy storage, has received considerable interest of late. ![]()
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