Self-Assembly of Discrete Oligomers of Naphthalenediimides in Bulk and on Surfaces.

Chemistry

Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.

Published: February 2024

AI Article Synopsis

  • - The study focuses on creating specific oligomers of alkyl-bridged naphthalenediimides (NDIs) and examining their structures in different environments, like bulk, solution, and at interfaces.
  • - Researchers used a method to link multiple NDI cores with various alkyl-diamines, revealing strong intermolecular interactions through photophysical property analysis.
  • - Findings suggest that both the chemical structure and the conditions of crystallization are crucial for achieving orderly nanoscale arrangements, with long unsaturated chains typically resulting in folded structures and saturated chains leading to stretched configurations.

Article Abstract

Here, we report on the synthesis of discrete oligomers of alkyl-bridged naphthalenediimides (NDIs) and study their molecular nanostructures both in bulk, in solution, and at the liquid-solid interface. Via an iterative synthesis method, multiple NDI cores were bridged with short and saturated alkyl-diamines (C and C ) or long and unsaturated alkyl-diamines (u C to u C ) at their imide termini. The strong intermolecular interaction between the NDI cores was observed by probing their photophysical properties in solution. In bulk, the discrete NDI oligomers preferentially ordered in lamellar morphologies, irrespective of whether a saturated or unsaturated spacer was employed. Moreover, both the molecular architecture as well as the crystallization conditions play a significant role in the nanoscale ordering. The long unsaturated alkyl chains lead preferably to folded-chain conformations while their saturated analogues form stretched arrangements. At the solution-solid interface, well-defined lamellar regions were observed. These results show that precision in chemical structure alone is not sufficient to reach well-defined structures of discrete oligomers, but that it must be combined with precision in processing conditions.

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http://dx.doi.org/10.1002/chem.202303107DOI Listing

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