Pentarylene‐ and Hexarylenebis(dicarboximide)s: Near‐Infrared‐Absorbing Polyaromatic Dyes

Abstract

In the red: The synthesis and optical properties of homologous ladder‐type near‐infrared‐absorbing chromophores, namely, two pentarylenebis(dicarboximide)s (green traces; see picture) as well as a hexarylenebis(dicarboximide) (yellow trace) have been studied. A strong bathochromic shift of the absorption maximum is noted with an increasing degree of annulation as is evident from the other traces.

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

“…The extension of the aromatic p-system along the molecular long axis does not only cause a bathochromic shift, which allows maxima of absorption from 580 to 950 nm, but also increases their absorption coefficients. [100,101] The particularity of the perylene dyes is that they offer the introduction of a diverse set of substituents at different positions within the chromophore scaffold. In this way, they can be decorated in the bay or in the peri positions (Fig.…”

Synthetic Multifunctional Nanoarchitecture in Lipid Bilayers: Ion Channels, Sensors, and Photosystems

“…For example, from the structural point of view, O-NDIs are just one out of many possible rigid-rod molecules beyond p-oligophenyls that promise access to new structures with new functions. [15][16][17][18][19][20][21][22][23][24][25] The imaginable variability of hoops beyond -sheets in barrel-stave supramolecules simply enormous. Access to transmembrane rigid-rod -stack architecture is naturally not limited to NDI -stacks.…”

“…20 Important for nanoarchitecture, this non-planarity is lost in the flattened rylene rods 4 from the Müllen group. 21 The longer versions of these rods are very interesting because they can harvest infrared light. Eaton's oligocubanes 5 are a spectacular example for a rich collection of non-aromatic and non-planar rigid rods in the literature.…”

“…11,12 Somehow the antithesis to foldamers, 13,14 these simple sturdy rods have attracted considerable scientific attention for applications in the materials sciences. [15][16][17][18][19][20][21][22][23][24][25] Highlights beyond the minimalist oligoacetylenes 17 1 and p-oligophenyls 18,19 2 include the oligonaphthalenes 3 studied in the Tsubaki group because of their exceptional stereochemical complexity ( Fig. 1).…”

New method for the synthesis of a highly-conjugated acene material and its application in Perovskite solar cells

“…16 Oligonaphthalenes could be synthesized through a remarkably direct one-step via a regioselective intermolecular four/six-component assembly, and they could serve as precursors to long aromatic systems. 17 Herein, we report the rapid transformation of oligonaphthalenes to nanographene-like structures, which have different conjugation lengths. Compared with the traditional synthetic methods, such as bromination and Suzuki coupling, used to synthesize acene, 18 this synthetic route is shorter since it has only two steps.…”