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Synthesis and Photocontrolled Supramolecular Self-Assembly of Azobenzene-Functionalized Perylene Bisimide Derivatives

1
Suzhou Key Laboratory of Macromolecular Design and Precision Synthesis, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
2
Global Institute of Software Technology, No 5. Qingshan Road, Suzhou National Hi-Tech District, Suzhou 215163, China
*
Author to whom correspondence should be addressed.
Polymers 2019, 11(7), 1143; https://doi.org/10.3390/polym11071143
Received: 6 May 2019 / Revised: 24 June 2019 / Accepted: 2 July 2019 / Published: 3 July 2019
(This article belongs to the Special Issue Photoresponsive Polymeric Materials)
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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. View Full-Text
Keywords: perylene bisimide; azobenzene; supramolecular assembly; photoisomerization; morphology control perylene bisimide; azobenzene; supramolecular assembly; photoisomerization; morphology control
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ling, W.; Cheng, X.; Miao, T.; Zhang, S.; Zhang, W.; Zhu, X. Synthesis and Photocontrolled Supramolecular Self-Assembly of Azobenzene-Functionalized Perylene Bisimide Derivatives. Polymers 2019, 11, 1143.

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