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1,7,9,10‐Tetrasubstituted PMIs Accessible through Decarboxylative Bromination: Synthesis, Characterization, Photophysical Studies, and Hydrogen Evolution Catalysis
Author(s) -
Costabel Daniel,
Skabeev Artem,
Nabiyan Afshin,
Luo Yusen,
Max Johannes B.,
Rajagopal Ashwene,
Kowalczyk Daniel,
Dietzek Benjamin,
Wächtler Maria,
Görls Helmar,
Ziegenbalg Dirk,
Zagranyarski Yulian,
Streb Carsten,
Schacher Felix H.,
Peneva Kalina
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004326
Subject(s) - ethylene glycol , photochemistry , perylene , chromophore , substituent , chemistry , excited state , visible spectrum , stacking , catalysis , aqueous solution , halogenation , materials science , organic chemistry , molecule , physics , optoelectronics , nuclear physics
In this work, we present a new synthetic strategy for fourfold‐substituted perylene monoimides via tetrabrominated perylene monoanhydrides. X‐ray diffraction analysis unveiled the intramolecular stacking orientation between the substituents and semicircular packing behavior. We observed the remarkable influence of the substituent on 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.