Ingénierie moléculaire des systèmes pi-conjugués

— Classic organometallic coupling reactions (Pd, Ni or Cu catalysts): Stille, Heck, Kumada, Sonogashira, Suzuki, Negishi.
— Direct arylations (directed or not), applications to aromatic heterocycles.
— Click chemistry (Cu, Ru) and C-H activation.
— Metathesis reactions, principles, (diastereo) selectivies.
— Amination and sulfuration reactions to design new syntheses of pi-conjugated systems.
— Interest of non noble metals in synthesis.
— Main electro- and photoactive organic derivatives.
- Nanocarbons: fullerenes, nanotubes and graphene.
- Perylene, naphthalene, porphyrin, phthalocyanin, tetrathiafulvalene.
- Pigments (diketopyrrolopyrrole, isoindigo, Bodipy etc …).
- Thiophene, furane, pyrrole, dithienopyrrole, fluorene, carbazole, phenylenevinylene, phenyleneethynylene …
- Organometallic complexes displaying optoelectronic properties.
— Design, synthesis, reactivity and functionalisation of these monomers.
— Design and synthesis of extended pi-conjugated systems (oligomers and polymers displaying a weak band gap).
— Analysis of structure/properties relationships and importance of these derivatives.
— Green chemistry applied to pi-conjugated molecules (12 principles of green chemistry, atom economy, calculations of E factor).

This teaching unit is dedicated to the main families of pi-conjugated systems used in organic electronics and photonics. The synthesis and functionalization of photo- and electroactive organic architectures will be discussed. A particular attention will be paid to the impact of functionalization over physico-chemical properties. In a pluridisciplinar manner, this unit will also raise awareness to the basic concepts of green chemistry and the interest of non-noble metals in synthesis.

─ Understand the reactivity of organometallic catalysts an their interest in molecular and macromolecular synthesis (C-C, C-heteroatom bond formation, direct arylations, metathesis).
─ Handle the main synthetic methods to prepare pi-conjugated systems (heterocy-clic chemistry, organometallic coupling reactions, polymerization strategies, cycload-ditions).
─ Design the retrosynthesis of a given pi-conjugated system by taking into account the concepts of green chemistry.
─ Understand the main principles of molecular engineering (polarity vs polarizability, extension and functionalisation of conjugated systems, dyes, pigments,...).
─ Comprehend the methods developed to fine-tune the levels of frontier orbitals and the band gap of molecular materials for organic electronics and photonics.
─ Use spectroscopic or electrochemical measurements to study a conjugated system and evaluate its potential in organic electronics.
- Know the main classes of molecular and macromolecular systems reported in the literature and their respective synthesis
- Differente nanocarbons and proposing well-suited functionalization strategies