Comprehensive Review on Synthesis, Properties, and Applications of Phosphorus (PIII, PIV, PV) Substituted Acenes with More Than Two Fused Benzene Rings

Abstract

This comprehensive review, covering the years 1968–2022, is not only a retrospective investigation of a certain group of linearly fused aromatics, called acenes, but also a presentation of the current state of the knowledge on the synthesis, reactions, and applications of these compounds. Their characteristic feature is substitution of the aromatic system by one, two, or three organophosphorus groups, which determine their properties and applications. The (PIII, PIV, PV) phosphorus atom in organophosphorus groups is linked to the acene directly by a P-Csp2 bond or indirectly through an oxygen atom by a P-O-Csp2 bond.

The First Example of the Friedel–Crafts Cyclization Leading to (10-Hydroxy-9,10-dihydroanthr-9-yl)phosphonium Salts without the Expected Bradsher Dehydration

“…A major advantage of this approach others known in the literature is the possibility of introducing a large numbe substituents of a different electron character, which rapidly change the photophy properties of the obtained acenes. In addition to the unique multiple substitution, in this study, we planned to defin increase the electron donor-acceptor properties of such acenes by introducing stron electron-withdrawing phosphonium groups (P + R 1 R 2 R 3 ) in order to obtain favor absorption and fluorescence properties [18][19][20]. Thus, following the hetero-F-C-B strat we planned to synthesize anthryl phosphonium salts III via intermediate (or acetalaryl)arylmethylphosphonium salts II (Z = P + R 1 R 2 R 3 ).…”

“…Advantageously, the synthesis of the latter was a one-pot reac bypassing the isolation of intermediate phosphonium salts II occurring through the d treatment of diarylmethanols I with various acids (HBF4, MeSO3H, HCl, TsOH) in presence of triphenyl-, diphenylmethyl-or dimethylphenylphosphine (Scheme 1). In addition to the unique multiple substitution, in this study, we planned to definitely increase the electron donor-acceptor properties of such acenes by introducing strongly electron-withdrawing phosphonium groups (P + R 1 R 2 R 3 ) in order to obtain favorable absorption and fluorescence properties [18][19][20]. Thus, following the hetero-F-C-B strategy, we planned to synthesize anthryl phosphonium salts III via intermediate (orthoacetalaryl)arylmethylphosphonium salts II (Z = P + R 1 R 2 R 3 ).…”

O,S-Acetals in a New Modification of oxo-Friedel–Crafts–Bradsher Cyclization—Synthesis of Fluorescent (Hetero)acenes and Mechanistic Considerations

“…Organic electronics and optoelectronics are relatively new fields of basic knowledge and technology, which have become a subject of interest to chemists, physicists and process engineers [ 1 ]. Therefore, a search for organic fluorescent and semiconducting materials for the construction of new-generation electronic devices, such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic solar cells (OPVs), organic solar concentrators (OSCs), organic lasers, etc., has drawn the attention of numerous multidisciplinary joint laboratories [ 2 ]. Among aromatic hydrocarbons, linearly fused acenes are being considered as key organic compounds for achieving these goals.…”

Highly Substituted 10-RO-(hetero)acenes—Electric Properties of Vacuum-Deposited Molecular Films

“…Linearly fused aromatic and heteroaromatic hydrocarbons, called (hetero)acenes, are an important group of compounds for applications in molecular optoelectronics. Unsubstituted or low-substituted acenes are the best known, but there is a lack of knowledge and general synthetic methods regarding higher-substituted analogues [1][2][3][4][5][6]. In addition, the more fused rings acenes contain (as pentacenes and higher analogs), the lower their stability.…”