This review serves as a brief introduction to phospholes and discusses their unique favorable properties for application in organic electronic materials. Over the past several years, π-conjugated phospholes have been slowly making their way into devices. We report here the mode of synthesis of these π-conjugated phospholes as well as discuss the performances of the devices.

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π-Conjugated phospholes and their incorporation into devices: components with a great deal of potential

This review presents the main class of organophosphorus compounds (triaryl phosphines, phosphazenes, phospholes, phosphetes and diphosphacyclobutanes), which have been used in electronic devices (organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPV cells), dye-sensitized solar cells (DSSCs), organic field-effect transistors (OFETs), and electrochromic cells).

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Organophosphorus derivatives for electronic devices

A synthetic route to planar P-modified polycylic aromatic hydrocarbons (PAHs) is described. The presence of a reactive σ3,λ3-P moiety within the sp2-carbon scaffold allows the preparation of a new family of PAHs displaying tunable optical and redox properties. Their frontier molecular orbitals (MOs) are derived from the corresponding phosphole MOs and show extended conjugation with the entire π framework. The coordination ability of the P center allows the coordination-driven assembly of two molecular PAHs onto a AuI ion.

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Dibenzophosphapentaphenes: Exploiting P Chemistry for Gap Fine-Tuning and Coordination-Driven Assembly of Planar Polycyclic Aromatic Hydrocarbons

Phosphorus-based materials have received widespread attention in recent years, in particular as possible candidates for practical application in organic electronics. The geometry and electronic nature of phosphorus make it a favorable heteroatom for property tuning in order to obtain better performing organic electronics. This Focus Review discusses recent structural modifications and syntheses of phosphorus-based materials, illustrates property tuning at the same time, and highlights specific examples for device applications.

Phosphorus‐Containing Materials for Organic Electronics

Benzofuran-fused Phosphole: Synthesis, Electronic, and Electroluminescence Properties

new angle: The insertion of a 2,2′-biphosphole subunit into π-conjugated systems offers a new way to control the HOMO-LUMO gap. Tuning of the dihedral angle (θ) between the two phosphorous heterocycles, either by metal coordination or covalent bonding through the P substitution can lead to control of the band gap. These new π-conjugated systems can be used as emitting materials in white organic light-emitting devices (WOLEDs).

2,2′‐Biphospholes: Building Blocks for Tuning the HOMO–LUMO Gap of π‐Systems Using Covalent Bonding and Metal Coordination

A DFT study suggests that the conversion of arsolylcarbenes into arsenines as described by Markl proceeds via arsabenzvalenes. A similar conversion does not work with phospholylcarbenes. However, we have found that, in some cases, 1-diazoalkylphosphole sulfides are converted into phosphinine sulfides whose in situ reduction by triphenylphosphite affords the dicoordinate phosphinines.

Jin Li

Papers

2,2′‐Biphospholes: Building Blocks for Tuning the HOMO–LUMO Gap of π‐Systems Using Covalent Bonding and Metal Coordination

Investigating the Phospholylcarbene to Phosphinine Conversion