Fully zwitterionic diaminobenzoquinonediimines promoted by cyanoaromatic N-substituents. Bousquet, Adrien Morice, Ugo Triballier, Gabriel Canard, Pavel Lhoták, Denis Jacquemin, Simon Pascal, Olivier Siri. The Journal of Organic Chemistry 2022, 87 Solvation Effects in Organic Chemistry: A Short Historical Overview. Synthesis of Asymmetric Coupled Polymethines Based on a 7-Chloropyridobenzimidazole-8,9-dione Core. Anastasija Gaile, Sergey Belyakov, Baiba Turovska, Nelli Batenko.Feasibility of p-Doped Molecular Crystals as Transparent Conductive Electrodes via Virtual Screening. Tahereh Nematiaram, Alessandro Troisi.This article is cited by 11 publications. This molecular design will generate small π-conjugated donor–acceptor molecules with small Δ E H–L values. The NIR absorption responds to solvent polarity, temperature, and acid addition. 1 eV and show amphoteric redox properties and near-infrared (NIR) electronic absorption exceeding λ = 1000 nm. The zwitterions with small Δ E D–A and large φ DA have a small Δ E H–L of ca. The energy difference between the HOMO of the anion and the LUMO of the cation (Δ E D–A) and the interplanar angle between them (φ DA) have a crucial effect on Δ E H–L, and hence, on the electronic structures and optoelectronic properties of these zwitterions. To develop relatively small donor–acceptor molecules with small Δ E H–L values, we have designed and synthesized π-conjugated zwitterions composed of electron-donating anions, such as phenoxide and anthroxide, and electron-accepting cations, such as pyridinium and acridinium. Although the expansion of π-conjugation is one of the well-known approaches for designing molecules with small Δ E H–L values, such an approach inevitably gives large π-conjugated molecules sometimes suffering from synthetic difficulty and low solubility toward organic solvents. Π-Conjugated molecules with small highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energy gaps (Δ E H–L) have been extensively studied because of their unique optoelectronic properties.
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