1,7,9,10-tetrasubstituted PMIs accessible via decarboxylative bromination: Synthesis, Characterization, Photophysical Studies and Hydrogen Evolution Catalysis

in: Chemistry-A European Journal (2021)
Costabel, Daniel; Skabeev, Artem; Nabiyan, Afshin; Luo, Yusen; Max, Johannes; Rajagopal, Ashwene; Kowalczyk, Daniel; Dietzek, Benjamin; Wächtler, Maria; Görls, Helmar; Ziegenbalg, Dirk; Zagranyarski, Yulian; Streb, Carsten; Schacher, Felix H.; Peneva, Kalina
In this work, we present a new synthetic strategy for fourfold substituted perylene monoimides via tetrabrominated perylene monoanhydrides. X-Ray diffraction analysis unveiled intramolecular stacking orientation between the substituents and semicircular packing behavior. We observed remarkable influence of the substituent to the longevity and nature of the excited state upon visible light excitation. In the presence of poly(dehydroalanine)‐graft‐poly(ethylene glycol) graft copolymers as solubilizing template, the chromophores are capable of sensitizing [Mo 3 S 13 ] 2- clusters in aqueous solution for stable visible light driven hydrogen evolution over three days.

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