Related Experiment Video
Updated: Jul 3, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
Visualization of various supramolecular assemblies of oligo(para-phenylenevinylene)-melamine and perylene bisimide
Freek J M Hoeben1, Jian Zhang, Cameron C Lee
1Laboratory of Macromolecular and Organic Chemistry Eindhoven University of Technology, Eindhoven, The Netherlands.
Abstract:
A melamine derivative has been covalently equipped with two oligo(para-phenylenevinylene) (OPV) chromophores. This procedure yields a bifunctional molecule with two hydrogen-bonding arrays available for complementary binding to perylene bisimide derivatives. Depending on the solvent, hydrogen-bonded trimers, tetramers, and dimers on a graphite surface are observed for pure OPV-melamine by using scanning tunneling microscopy (STM). Upon the addition of perylene bisimide, linear tapes of perylene bisimide, 12-membered rosettes that consist of alternating hydrogen-bonded OPV-melamine and perylene bisimide moieties are visualized. These results provide direct evidence for the possible modes of hydrogen bonding within a supramolecular co-assembly in solution. Subsequently, the optical properties of pure OPV-melamine and co-assemblies with a perylene bisimide derivative were characterized in solution. In an apolar solvent, OPV-melamine self-assembles into chiral superstructures. Disassembly into molecularly dissolved species is reversibly controlled by concentration and temperature. Complementary hydrogen bonding to a perylene bisimide derivative in an apolar solvent yields multicomponent, pi-stacked dye assemblies of enhanced stability that are characterized by fluorescence quenching of the constituent chromophores. Titration experiments reveal that a mixture of hydrogen-bonded oligomers is present in solution, rather than a single discrete assembly. The solution experiments are consistent with the STM results, which revealed various supramolecular assemblies. Our system is likely not to be optimally programmed to obtain a discrete co-assembled structure in quantitative yield.
Related Concept Videos
Molecular Models
Newman Projections
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as conformers.
Characteristics and Nomenclature of Copolymers
Structure of Benzene: Molecular Orbital Model
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

