Synthesis and Supramolecular Assembly of a Terrylene Diimide Derivative Decorated With Long Branched Alkyl Chains

• Main Authors: Zongxia Guo, Xiao Zhang, Lu Zhang, Yujiao Wang, Weisheng Feng, Kai Sun, Yuanping Yi, Zhibo Li
• Format: Article
• Language: English
• Published: Frontiers Media S.A. 2019-07-01
• Series: Frontiers in Chemistry
• Subjects: terrylene diimides; supramolecular assembly; scanning tunneling microscope; aromatic systems; liquid-solid interface
• Online Access: https://www.frontiersin.org/article/10.3389/fchem.2019.00473/full

Terrylene diimide derivatives are pigments for dyes and optoelectric devices. A terrylene diimide derivative N,N'-di(1-undecyldodecyl)terrylene-3,4:11,12-tetracarboxdiimide (DUO-TDI) decorated with long branched alkyl chains on both imide nitrogen atoms was designed and synthesized. The supramolecular assembly behaviors of DUO-TDI in solution and at the liquid-solid interface were both investigated. The assembled nanostructures and photophysical properties of TDI in solution were explored by varying solvent polarity with spectral methods (UV-Vis, FL and FT-IR) and morphological characterization (AFM). Depending on the solution polarities, fibers, disk structures and wires could be observed and they showed diverse photophysical properties. In addition, the interfacial assembly of DUO-TDI was further investigated at the liquid-Highly Oriented Pyrolytic Graphite (HOPG) interface probed by scanning tunneling microscope (STM). Long range ordered monolayers composed of lamellar structures were obtained. The assembly mechanisms were studied for DUO-TDI both in solution and at the interface. Our investigation provides alternative strategy for designing and manipulation of supramolecular nanostructures and corresponding properties of TDI based materials.