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• W2999698093 abstract "Dianionic bis(benzenesulfonate)–naphthalenediimide (BSNDI2–) formed simple 2:1 cation–anion salts of (NH4+)2(BSNDI2–) (1), (CH3NH3+)2(BSNDI2–) (2), (C2H5NH3+)2(BSNDI2–) (3), [(C2H5)2NH2+]2(BSNDI2–) (4), and [(C2H5)3NH+]2(BSNDI2–) (5). The thermal stability, crystal structure, electron transport properties, and dielectric response were evaluated for these systems in terms of π-electron density and dimensional crossover from two-dimensional (2D) and one-dimensional (1D) to zero-dimensional (0D) electronic structures. Systematic modification of the counter cations from NH4+ to simple alkylammoniums (CH3NH3+, C2H5NH3+, (C2H5)2NH2+, and (C2H5)3NH+) for BSNDI2– salts affected the packing π-density and dimensionality of NDI π-cores. All single crystals formed alternating cation–anion layers, where the intermolecular interactions in salts 1, 2, 3, 4, and 5 were observed as dense 2D brickstone, 1D column, 1D column, dilute 2D herringbone, and isolated 0D monomer arrangements, respectively. The π-electron occupation percentage in the unit cell of salts 1, 2, 3, 4, and 5 decreased in that order, at 96.2%, 87.8%, 83.8%, 78.8%, and 72.6%, respectively, where the intermolecular π–π interaction between BSINDI2– anions was gradually diluted on increasing in the cation volume. The transfer integrals between the lowest unoccupied molecular orbital in salts 1–5 clearly indicated a dimensional crossover from 2D to 1D to 0D electronic structures. Flash-photolysis time-resolved microwave conductivity measurements of salts 1, 2, 3, and 4 helped determine the magnitude of electron carrier mobility, which followed the order 1 > 2 ≈ 3 ≈ 4. The dielectric response of salt 1 being an order of magnitude higher than those of salts 2–5 was associated with the protonic conductivity in the NH4+···–SO3– electrostatic hydrogen-bonding network layer. Simple cation exchange in dianionic BSNDI2– salts conventionally modified the intermolecular π–π interactions in terms of dimensionality, magnitude, and electron transport properties." @default.
• W2999698093 created "2020-01-23" @default.
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• W2999698093 date "2020-01-09" @default.
• W2999698093 modified "2023-09-27" @default.
• W2999698093 title "Density and Dimensional Control of π-Electrons in Electrostatically Binding Naphthalenediimide Salts" @default.
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• W2999698093 doi "https://doi.org/10.1021/acs.cgd.9b01526" @default.
• W2999698093 hasPublicationYear "2020" @default.
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