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Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
Published on: August 20, 2018
Self-assembled thermally highly stable 1-dimensional proton arrays.
In-Chul Hwang1, Sung Woo Heo, N Jiten Singh
1Department of Chemistry, Center for Superfunctional Materials, Pohang University of Science and Technology, Pohang 790-784, Korea.
The Journal of Physical Chemistry. B
|May 8, 2010
Summary
Novel proton complexes of polyaromatic hydrocarbon aldehydes exhibit one-dimensional proton arrangement. These strong hydrogen-bonded structures, stabilized by pi-pi interactions, offer insights into intermolecular bonding.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Crystallography
Background:
- Polyaromatic hydrocarbons (PAHs) are hydrophobic compounds with diverse applications.
- Intermolecular hydrogen bonding plays a crucial role in molecular self-assembly and material properties.
- Proton complexes involving aldehydes of PAHs are underexplored.
Purpose of the Study:
- To synthesize and characterize novel proton complexes of polyaromatic hydrocarbon aldehydes.
- To investigate the nature and strength of intermolecular hydrogen bonding in these complexes.
- To elucidate the structural features and proton arrangement within the complexes.
Main Methods:
- Synthesis of proton complexes via reaction of 9-antraldehyde with HAuCl(4) under dry conditions.
- Single-crystal X-ray structure determination to analyze molecular arrangement and bonding.
- Infrared (IR) spectroscopy at varying temperatures to study hydrogen bond dynamics and characteristics.
- Analysis of electron density and chemical shifts to confirm strong hydrogen bonding.
Main Results:
- Formation of a novel proton complex: [(Ant-CHO)(2)H](+)[AuCl(4)](-).
- Observation of a one-dimensional proton arrangement within a Zundel-like cationic hydrogen bond (O-H(+)-O).
- Characterization of very strong, short hydrogen bonds with an O-H(+)-O distance of approximately 2.4 Å and a large downfield 1H NMR chemical shift (20.18 ppm).
- Stabilization of the layered structures by pi-pi intermolecular interactions between PAH ligands.
- Identification of characteristic IR spectral signatures for the Zundel-like proton bond.
Conclusions:
- The study successfully synthesized and characterized novel proton complexes of polyaromatic hydrocarbon aldehydes.
- These complexes exhibit strong, short intermolecular hydrogen bonds with a unique one-dimensional proton arrangement.
- The findings contribute to the understanding of supramolecular assembly driven by hydrogen bonding and pi-pi interactions in PAH derivatives.
