title: Divergent strategy for the synthesis of original dihydrobenzo- and dihydronaphtho-acridines.
abstract: A straightforward access to numerous novel substituted dihydrobenzo- and dihydronaphthoacridines is described using a unique molecular platform in two key steps. A large range of carbon-based substituents such as aromatic, vinyl, alkynyl fragments through Pd-catalysed couplings has been installed. The molecular diversity is extended to the introduction of aza-heterocycles and further authorizes the installation of alkylamino chains by means of Cu-promoted C-N bond formation. Possible access to quinolinium salts is also described. The methodology revealed convenient preparation of a wide panel of molecules that display various rigidity/flexibility and lipophilic/hydrophilic balances. Finally, the influence of structural modulations on the photophysical properties of these novel architectures is also studied. It is noteworthy that styryl and alkynyl derivatives are emissive in water (ϕF up to 12%).
authors.affiliation: Université de Versailles Saint-Quentin-en-Yvelines, Institut Lavoisier de Versailles, UMR CNRS 8180, 45, Avenue des Etats-Unis, 78035 Versailles cedex, France. damien.prim@.uvsq.fr anne.gaucher@uvsq.fr.
authors.forename: Kathleen
authors.initials: K
authors.lastname: Solmont
authors.forename: Hamza
authors.initials: H
authors.lastname: Boufroura
authors.forename: Amel
authors.initials: A
authors.lastname: Souibgui
authors.forename: Pauline
authors.initials: P
authors.lastname: Fornarelli
authors.forename: Anne
authors.initials: A
authors.lastname: Gaucher
authors.forename: Florence
authors.initials: F
authors.lastname: Mahuteau-Betzer
authors.forename: Béchir
authors.initials: B
authors.lastname: Ben Hassine
authors.forename: Damien
authors.initials: D
authors.lastname: Prim
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000166:Acridines