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RESEARCH PRODUCT
Practical Syntheses of Terrylene Chromophores from Naphthalene and Perylene Building Blocks
Daniel UersfeldDaniel UersfeldSebastian StappertSebastian StappertKlaus MüllenKlaus MüllenChen LiChen Lisubject
010405 organic chemistryChemistryGeneral ChemistryChromophore010402 general chemistry01 natural sciences0104 chemical scienceslaw.inventionCatalysischemistry.chemical_compoundColumn chromatographylawOrganic chemistryCrystallizationPeryleneNaphthalenedescription
A facile and efficient method to synthesize terrylene imides, a unique class of chromophores, and their derivatives from commercially available naphthalene and perylene building blocks is reported. We developed an extremely efficient Suzuki/C-H-arylation coupling cascade with Pd2(dba)3/PCy3 (dba = dibenzylidenacetone, Cy = cyclohexyl) as the catalyst and highly soluble naphthalene derivatives as starting materials. This efficiency allows purification via precipitation and crystallization, avoiding time-consuming column chromatography. For the first time, the highly soluble 3,4,11,12-terrylene tetraester was prepared in gram scale with yields up to 75 % which thus becomes a versatile starting material for the synthesis of new terrylene derivatives. The presented method not only allows the synthesis of terrylene dyes and pigments, but also presents a route towards perylene and terrylene monoimides which is an advantageous simplification of previously reported synthetic procedures.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-10-12 | Advanced Synthesis & Catalysis |