A conformational analysis of mono and dialkyl ethers of 2,2′‐dihydroxy‐1,1′‐binaphthalene by circular dichroism spectroscopy and cholesteric induction in nematic liquid crystals
Authors:
Abstract
The coupling of the analysis of the absorption and circular dichroism (CD) spectra with that of the cholesteric mesophases induced in nematic liquid crystals indicated some interesting conformational features of bridged and nonbridged mono‐ and dialkylethers of optically active 2,2′‐dihydroxy‐1,1′‐binaphthalene. Bridged derivatives are characterized by relatively small dihedral angles. Simple monoalkyl ethers are characterized by larger dihedral angles but they all assume an s‐cis conformation, owing to the existence of intramolecular hydrogen bonds. Nonbridged dialkylethers prefer even larger dihedral angles and, depending on the bulkiness of the alkyl groups, the s‐trans conformation can be found. Interestingly, the conformation of dialkylethers is strongly dependent on the structure of the liquid crystal solvent, because the intramolecular hydrogen bond is not possible there.Keywords
This publication has 20 references indexed in Scilit:
- Chirochromism-Photochromism by Epimerization: Search for a Liquid Crystal PhototriggerJournal of the American Chemical Society, 1994
- Solution conformation of two C2-symmetric amino derivatives of 1,1'-binaphthalene by circular dichroism and liquid crystal techniqueThe Journal of Organic Chemistry, 1992
- Photoracemization of optically active 1,1'-binaphthyl derivatives: light-initiated conversion of cholesteric to compensated nematic liquid crystalsThe Journal of Physical Chemistry, 1992
- A study of the conformation of some chiral binaphthyl and bithienyl derivatives in the solid state and in solution. An approach by X-ray diffraction, circular dichroism spectroscopy and induced cholesteric mesophase analysisJournal of the Chemical Society, Perkin Transactions 2, 1992
- Direct chirality determination of secondary carbinol by chirality recognition ability of C2 symmetry 1,1'-binaphthyl-2,2'-diyl phosphoryl chlorideJournal of the American Chemical Society, 1990
- Centenary Lecture. Chemical multiplication of chirality: science and applicationsChemical Society Reviews, 1989
- Induced Cholesteric Mesophases as a Probe for the Stereochemistry of Chiral BiphenylsBulletin of the Chemical Society of Japan, 1986
- Angular dependence of the u.v. absorption maximum wavelength in exciton coupling systemsJournal of the Chemical Society, Chemical Communications, 1982
- Optical rotatory power of 2,2'-dihydroxy-1,1'-binaphthyl and related compoundsJournal of the American Chemical Society, 1972
- Configuratio, Conformation and Rotatory Dispersion of Optically Active BiarylsJournal of the American Chemical Society, 1962