Thermally Stable Intermolecular Proton Bonds in Polyaromatic Aldehyde Crystals
SCIE
SCOPUS
- Title
- Thermally Stable Intermolecular Proton Bonds in Polyaromatic Aldehyde Crystals
- Authors
- Heo, SW; In Chul Hwnag; Chun, Y; Jung Woo Lee; n. Jiten Singh; Kim, SB; Kim, KS
- Date Issued
- 2011-08-01
- Publisher
- WILEY-BLACKWELL
- Abstract
- We have synthesized self-assembled red-colored proton complexes of the aldehyde derivatives of polyaromatic hydrocarbon with strong intermolecular hydrogen bonding. These intermolecularly proton-bonded polyaromatic aldehydes formed as 1-pyrene-carbaldehyde (Py-CHO) reacted with HAuCl4 to produce [(Py-CHO)(2)H]-[AuCl4] under dry conditions. The formation of [(Py-CHO)(2)H][AuCl4] was confirmed by single-crystal structure determination and IR spectral analysis at various temperatures. The compounds are distinctively hydrophobic in nature and are soluble only in a few organic polar solvents. The proton bonds are clearly observed from both the electron density in X-ray analysis and the characteristic IR frequency signature. The proton complex units have an O-H+-O distance of the typical Zundel-like cationic hydrogen bond (in which two O atoms share a proton-like H in the midpoint of the short O-O distance of approximate to 2.4 angstrom). The proton bonds are thermally stable, even over 100 degrees C, because the complexes are stabilized in layered structures with pi-pi intermolecular interactions of the polyaromatic hydrocarbon ligands. The IR signatures at around 900, 1200, and 1700 cm(-1) for the Zundel-like proton bond are clearly characterized.
- Keywords
- crystal engineering; density functional calculations; hydrogen bonds; IR spectroscopy; proton bonds; STRONG HYDROGEN-BONDS; WATER CLUSTERS; AB-INITIO; VIBRATIONAL FREQUENCIES; AROMATIC-HYDROCARBONS; MOLECULAR RECOGNITION; BINDING-ENERGIES; PI-INTERACTION; SPECTRA; BENZENE
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/17104
- DOI
- 10.1002/ASIA.201100130
- ISSN
- 1861-4728
- Article Type
- Article
- Citation
- CHEMISTRY-AN ASIAN JOURNAL, vol. 6, no. 8, page. 2054 - 2060, 2011-08-01
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