title: Synthesis of regioisomerically pure 1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid derivatives.
abstract: The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the "peri" and the "bay" positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.
authors.affiliation: Laboratory of Organic Materials & Interfaces and ‡Laboratory of Optoelectronic Materials, Department of Chemical Engineering, Delft University of Technology , Julianalaan 136, 2628BL Delft, The Netherlands.
authors.forename: Sanchita
authors.initials: S
authors.lastname: Sengupta
authors.forename: Rajeev K
authors.initials: RK
authors.lastname: Dubey
authors.forename: Rob W M
authors.initials: RW
authors.lastname: Hoek
authors.forename: Sjoerd P P
authors.initials: SP
authors.lastname: van Eeden
authors.forename: D Deniz
authors.initials: DD
authors.lastname: Gunbaş
authors.forename: Ferdinand C
authors.initials: FC
authors.lastname: Grozema
authors.forename: Ernst J R
authors.initials: EJ
authors.lastname: Sudhölter
authors.forename: Wolter F
authors.initials: WF
authors.lastname: Jager
mesh_terms: D002087:Butyrates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000592967:1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester; D002087:Butyrates; D010569:Perylene