Abstract
Azobenzene (Azo) units were successfully introduced into perylene bisimide (PBI) structures in order to realize the photocontrolling of the morphology of the supramolecular assembly of PBI by a photoisomerization process. A total of three Azo-functionalized perylene bisimide derivatives (PBI1, PBI2, and PBI3) with different alkyl chain lengths were designed and synthesized by imidization of 3,4,9,10-perylene tetracarboxylic dianhydride with the corresponding amines. The structures of these compounds were characterized by proton nuclear magnetic resonance (1H NMR) and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS). The photoisomerization behaviors of Azo units in PBIs were investigated using ultraviolet-visible (UV-VIS) absorption spectroscopy, which were obviously effected by solvents and the alkyl chain length. Furthermore, the photoisomerization of Azo units has the obviously regulatory effect on the morphology of supramolecular assembly of PBIs, especially for the medium-length alkyl chain-linked Azo-functionalized PBI derivative (PBI2). This research realized the photocontrolling of the morphology of the supramolecular assembly of PBI derivatives by photoisomerization of Azo units.
Highlights
The Azo-functionalized Perylene tetracarboxylic acid bisimides (PBI) derivatives (PBIs 1–3) with different alkyl chain lengths were synthesized by imidization of 3,4,9,10-perylene tetracarboxylic dianhydride with corresponding amines as shown in Scheme 1
The structures of PBIs 1–3 were characterized by 1 H NMR and MALDI-TOF-MS spectra
We chose DMSO-d6 as solvent for PBIs 1–3 were s (PBI1) and CDCl3 for PBI2 and PBI3 according to their different solubility for NMR measurement
Summary
Perylene tetracarboxylic acid bisimides (PBI) have attracted considerable attention on account of their luminescence [1,2,3,4,5,6], n-type semiconductor [7,8,9,10,11] properties in the past few decades, and have found a use as applications in sensors [12], lasers [13], drug release [14], organic electronic devices [15], supramolecular self-assemblies [16], and so on. Würther and co-workers first reported the formation of J-aggregates by supramolecular design principles [25] They presented the successful transformation from H- to J-aggregates of PBI driving by hydrogen-bond directed complexation between melamine and cyanurate units [26]. Azobenzene (Azo) is one of the classical photoresponsive compounds, the drastic changes of which both in the structure and properties can be caused by the reversible trans-cis isomerization process This special property of Azo has been used to regulate the morphology of aggregates [31,32], supramolecular chirality [33,34,35], and gelation property [36,37]. Our group reported the morphology and chirality control of supramolecular structure of achiral Azo-containing polymers in the chiral solvent by reversible trans-cis isomerization of Azo chromophore [40]. The effects of different alkyl chain lengths on the Azo photoisomerization behavior and the further influence on the PBI nanostructures were investigated
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