Multi‐Stage Redox Systems Based on Dicationic P‐Containing Polycyclic Aromatic Hydrocarbons

Abstract

Scheme 2. Synthetic access to 2[OTf]2 and chemical structure of compounds 3-6 2+ (TfOanions have been omitted for clarity)

Luminescent Molecular Switches Based on Dicationic P-Doped Polycyclic Aromatic Hydrocarbons

“…In short, we prepared three new P-containing PAHs with variable exocyclic P-substituents and C-substituents and a 8 or exocyclic substituents 2 , Scheme 1).…”

Exploitation of Baird Aromaticity and Clar’s Rule for Tuning the Triplet Energies of Polycyclic Aromatic Hydrocarbons

“…Polycyclic aromatic hydrocarbons (PAHs) are a fascinating class of molecules providing versatile organic semi-conductors [1] for a variety of use cases such as photovoltaics [2] including singlet fission [3,4], charge transport [5], and field-effect transistors [6]. Due to their high tunability, PAHs and their derivatives are also particularly suitable for more intricate applications such as logic gates [7], single molecule conductance [8,9], thermoelectrics [10], and multi-stage redox systems [11]. Ever more intricate PAH structures are being synthesised [12,13] and ever more detailed spectroscopic experiments performed [14][15][16].…”

Cationic Organophosphorus Chromophores: A Diamond in the Rough among Ionic Dyes

“…An elegant single‐step procedure has been pioneered by Wang and co‐authors, who applied a copper(II)‐mediated cycloaddition of alkynes to tertiary phosphines, yielding five‐ ( 32 ) or six‐membered ( 33 ) P‐heterocyclic cations in high yields (Scheme 11 A). [58] The method has been successfully extended by Bouit to PAH‐based diphosphines (naphthalene, pyrene, anthracene, chrysene) with high regioselectivity of bisphosphaacenium cycles [60] …”

“…An interesting set of dicationic molecules (selected examples 50 – 52 are given in Figure 17) has been recently described by Bouit and co‐workers, prepared from tertiary diphosphines and diphenylacetylene (method A, Scheme 11). [60] Decoration of the naphthalene with phosphininium rings produces 1,8‐bisphosphapyrenium 50 scaffold with orange fluorescence ( λ em =606 nm, Φ em =0.19 in CH 2 Cl 2 ). The extension of the acene framework from naphthalene to chrysene ( 51 ) however induces blue shift of the emission ( λ em =560 nm, Φ em =0.06 in CH 2 Cl 2 ).…”