Amino-substituted rylene dicarboximides and their quinoidal charge delocalization after deprotonation

Beyond perylene diimides: synthesis, assembly and function of higher rylene chromophores

“…For example, the structural analysis of 106 was done by calculating the X-ray pattern based on molecular dynamic simulation in which the discs equilibrated into a helical structure having an intermolecular rotation angle of 45 . In contrast, solid-state NMR studies on 106 suggested a little broader range for the rotation angle (30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43)(44)(45) which was mainly assigned to the out of plane rotation of the bulky alkyl side chains toward the aromatic core. When deposited on a substrate (e.g.…”

“…Upon addition of a base and subsequent removal of the amino proton, the negative charge is delocalized at the imide oxygen resulting in a quinoidal structure (Scheme 16, red color). 43 This type of conjugation is responsible for vast bathochromic shi increases with increasing molecular size, resulting in a giant bathochromic shi of 435 nm for the quaterrylene derivative 79d. Amination of imides 77a-d introduced a "push-pull" effect to the molecules resulting in bathochromic shis of 16-91 nm.…”

Perylenes as sensitizers in hybrid solar cells: how molecular size influences performance

“…1). 37,38 Moreover, due to their outstanding photophysical and photochemical stability as well as their high fluorescence quantum yields, perylenes have been used as excellent materials for single molecule spectroscopy. 39 The same set of favorable properties also makes perylenes important active components for application in organic electronic devices.…”

Enhanced Intramolecular Charge Transfer in New Type Donor–Acceptor Substituted Perylenes

“…Consequently, the substituents at the quinoline part of the chromophore protect the nitrogen atom from oxidation and provide a higher chemical stability. This seems to be due both to the increased push–pull effect as well as to the steric hindrance …”