10.1016/j.tet.2008.08.054
This research describes the synthesis, characterization, and self-assembly of supramolecular oligo-phenylene-ethynylene (OPE) wires, which are bridged bis-Hamilton receptors, and their interaction with a cyanuric acid-modified tetraphenylporphyrin (TPP). The purpose of the study was to investigate the electronic, photoluminescence, and electroluminescence properties of these π-conjugated systems, which are relevant for their potential use as nanowires between electrodes. The researchers synthesized new OPE bridged bis-Hamilton receptors and characterized their linear H-bonding behavior with the modified TPP. The resulting complexes were analyzed using 1H NMR, UV/vis, and fluorescence spectroscopies, and the association constants and cooperativity of binding were determined. The study concluded that the self-assembled structures formed 1:2 complexes with strong association constants, indicating a robust supramolecular interaction. No electronic communication was detected between the OPE wires and the porphyrin, suggesting that OPEs can serve as inactive bridges in supramolecular donor-acceptor arrays. Key chemicals used in the process included 5-iodo-xylene, KMnO4, thionyl chloride, aminopyridine derivatives, trimethylsilylacetylene, TBAF, and various catalysts and solvents for the coupling and deprotection reactions.
10.1021/ja010664o
The research focuses on the thermodynamic stabilities of different structural assemblies formed by the self-assembly of N,N-disubstituted melamines and N-substituted cyanuric acid or 5,5-disubstituted barbituric acid derivatives through hydrogen bond formation. The study employs a model that considers various stereoisomeric tape structures and a cyclic hexameric rosette structure, incorporating steric parameters to represent different types of steric interactions within the assemblies. The main content revolves around model calculations for these self-assemblies, taking into account all possible stereoisomeric tape structures consisting of two to eight components and one cyclic hexameric rosette structure. The model includes eight steric parameters to represent the steric interactions within the assemblies. The experiments involved the synthesis of various melamine and cyanuric acid derivatives, which were then allowed to self-assemble into different structures. The analysis included 1H NMR spectroscopy to monitor chemical shift changes, vapor pressure osmometry (VPO) to determine association constants, and various other analytical techniques such as mass spectrometry (MS) and elemental analysis to characterize the synthesized compounds and their assemblies. The research also utilized computer simulations to study the effect of changing melamine substituents on the shape and thermodynamic stability of the corresponding rosette and tapelike assemblies.
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