1,7,9,10‐Tetrasubstituted PMIs Accessible through Decarboxylative Bromination: Synthesis, Characterization, Photophysical Studies, and Hydrogen Evolution Catalysis

Abstract

In this work, we present an ew synthetics trategy 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.W eo bserved the remarkable influence of the substituent on the longevity and nature of the excited state upon visible light excitation.I nt he presenceo fp oly(dehydroalanine)-graftpoly(ethylene glycol)g raft copolymers as solubilizing template, the chromophores are capable of sensitizing [Mo 3 S 13 ] 2À clustersi na queous solution for stable visible light driven hydrogen evolution over three days.

PEGylation of Guanidinium and Indole Bearing Poly(methacrylamide)s – Biocompatible Terpolymers for pDNA Delivery

“…The synthesis of PMIM was achieved in five steps starting from dibutyl‐1,6,9,10‐tetrabromoperylene 3,4‐dicarboxylate (Compound 1 in Scheme S1, Supporting Information). [ 53 ] Nucleophilic aromatic substitution with phenol resulted in dibutyl‐1,6,9,10‐tetraphenoxyperylene 3,4‐dicarboxylate ( 2 ) and acidic ester hydrolysis afforded perylene monoanhydride ( 3 ). For the imidization involving N ‐Boc‐1,6‐hexanediamine, imidazole was used as solvent with catalytic amounts of zinc acetate to give the respective perylene monoimide ( 4 ).…”

Perylene Monoimide as a Versatile Fluoroprobe: The Past, Present, and Future

“…Recently, Penevaʼs group reported a synthetic procedure in which they have reported the synthesis of 1,6,9,10-and 1,7,9,10-tetrabromoperylene-3,4-dibutylester in three steps from perylene 3,4,9,10-dianhydride (4). 28 Figure 3 The synthetic pathway of PMI first reported by Langhalsʼ group. 23a Figure 4 Another synthetic strategy of PMI as reported by Xiaoʼs group.…”

“…The newly discovered compounds were characterized by several spectroscopic and electrochemical techniques. 28 But, the most enthralling story lies in their hydrogen evaluation catalytic activity. They have used the tetra-substituted PMI as PS in combination with (NH 4 ) 2 [Mo 3 S 13 ]•2H 2 O as the hydrogen evaluation catalyst.…”

Double hydrophilic copolymers – synthetic approaches, architectural variety, and current application fields

“…The properties of DHCs are often superior compared to their linear DHBC counterparts, and are already foreseen to be promising materials in different application fields, e.g. , sensing, 15 catalysis 12,48 or as drug delivery systems. 17 Together with the concept of multi-hydrophilicity, the topology can be seen as an additional parameter to tune the DHC properties to tailor-make water-soluble polymeric materials.…”

“…However, the application field of DHCs expanded rapidly, and this polymer class is recently used in biomedical applications, as nanocarriers and imaging/contrast agents, in catalysis, sensing, or within hybrid materials and this is also highlighted here. 12,15,33,44,48–50 Their water-solubility, together with their potential binding sites, renders DHBCs suitable organic components for hybrid materials in aqueous environments, and their combination with various inorganic materials was found to yield high performance materials. 33,51…”