Role of intrinsic hydrogen bonds in the assembly of perylene imide derivatives in solution and at the liquid–solid interface. Issue 34 (17th August 2017)

• Record Type: Journal Article
• Authors: Guo, Zongxia; Wang, Kun; Yu, Ping; Zhang, Shengyue; Sun, Kai; Li, Zhibo
• Is Part Of: Physical chemistry chemical physics. Volume 19:Issue 34(2017)
• Page Start: 23007
• Page End: 23014
• Publication Date: 2017-08-17
• Subjects: Chemistry, Physical and theoretical -- Periodicals; 541.3
• DOI: 10.1039/c7cp04928e
• Languages: English
• ISSNs: 1463-9076

Abstract

Abstract : The impact of hydrogen bond formation on the supramolecular assembly of two perylene imide-based derivatives was systematically investigated. Abstract : The impact of hydrogen bond formation on the supramolecular assembly of two perylene imide derivatives (PMAMI andPDINH ) was systematically investigated in solution and at the liquid–solid interface.PDINH has intrinsic hydrogen bond sites, but this is not the case forPMAMI . The solution assembly was explored by morphological methods (SEM, AFM, TEM and cryo-TEM) and spectral characterization (UV-vis, FL, XRD, and FTIR spectra). The surface assembly at the liquid–solid interface was detected by scanning tunneling microscopy (STM). It was found that in a mixed solution (THF/MeOH, 10 v%/90 v%), PMAMI formed nanofibers together with large sheet structures andPDINH assembled into uniform nanosheets, suggesting different molecular packing routes. The assembled structures could be adjusted by varying the solvent polarity for both molecules. At the liquid–solid interface, clearly distinguished surface nanostructures fromPMAMI andPDINH were easily observed. Based on all spectral and morphological characterizations, it was suggested that in solution the assembly ofPMAMI was mainly derived by π–π stacking interactions; on the other hand, the synergetic interaction of hydrogen bonds and π–π stacking was the reason for the hierarchical assembly ofPDINH . Hydrogen bonds could be formed both forPMAMI andPDINH and stabilized nanostructures at the liquid–solid interface. This investigation could be useful in designing perylene imide-based building blocks for fabricating supramolecular assemblies with predetermined nanostructures and properties.