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Organosphosphorus π-conjugated systems

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M. Hissler - P.-A. Bouit - T. Reynaldo

1- Organosphosphorus π-conjugated oligomers and polymers

We develop phospholes (1) as building block for π-system engineering. The weak aromaticity of phosphole allows the synthesis of chromophore/fluorophore with appealing properties. Tailoring the substituents at the 2 and 5 position allows HOMO-LUMO gap tuning. Phosphole-based semi-conducting polymers have also been synthesized. Di-phospholes linked through a P-P bond allows to prepare compounds with unusual σ-π conjugation and reduced HOMO-LUMO gap. Coordination chemistry at the P-atom permit to modify the optical properties and the arrangement of the compounds. Finally, these compounds were successfully introduced into colored and white OLED.

Publications significatives

Angew. Chem. Int. Ed. 2000, 39, 1812; Chem. Commun. 2002, 1674; J. Am. Chem. Soc. 2003, 125, 9254; J. Am. Chem. Soc. 2004, 126, 6058; J. Am. Chem. Soc. 2006, 128, 983; Angew. Chem. Int. Ed. 2006, 45, 6152-6155; Adv. Mat. 2009, 20, 1; Adv. Func. Mater. 2012, 22, 567; Angew. Chem. Int. Ed. 2012, 51, 214; Org. Letters 2013, 15, 330; J. Mater. Chem. C 2016, 4, 3686; Chem. Soc. Rev. 2016,10.1039/C6CS00257A.

2 - P-containing PAHs

In this project we synthesized the first example of polycyclic aromatic hydrocarbons (PAH) featuring a P-atom. P-reactivity allows unprecedented fine tuning of HOMO-LUMO gap and coordination driven assembly in the solid state. These compounds were also inserted into white-OLEDs.

Significant Publications

J. Am. Chem. Soc. 2012, 134, 6524-6527; Chem. Eur. J. 2015, 21, 6547; Dalton Trans. 2016, 45, 1896.

3 - Electronic properties of P-heterocycles

Organophosphorus chemistry give rise to a great variety of pi-conjugated systems depending on the size of the heterocycle (4-5-6 membered ring) or the hybridation of the P atom. In the frame of different collaborations (COST Phoscinet, COST EuSips, LIA FOM ...), we explored the electronic properties of unusual pi-conjugated P-scaffolds (phosphetes, phosphinines) thus paving the way to novel functional building blocks for opto-electronic applications.