Head-to-tail assemblies of dipolar, piperazine-linked chromophores: Synthesis, x-ray structure, and dielectric characterization
- AT T Bell Labs., Murray Hill, NJ (USA)
A dimer and a mixture of oligomers of acceptor-substituted anilines were prepared, either by Knoevenagel condensation of substituted cyanoacetylpiperazines with p-aminobenzaldehydes or by carbonyldiimidazole-promoted coupling of phenylpiperazines with p-aminocyanocinnamic acids. The resulting oligomeric amidopiperazines possess significantly additive molecular moments when in extended conformations and therefore are potentially valuable for the fabrication of polymer films containing electric field oriented chromophores, such as required for second-order nonlinear optics. The dimer is conformationally defined, and x-ray structural analysis of a model compound confirmed the stereochemistry and bond angles at the amide linkage. The enforced extended conformation of the dimer resulted in an enhanced dipole moment relative to the constituent monomers and raises the possibility of further enhancements in extended higher oligomers.
- OSTI ID:
- 6724226
- Journal Information:
- Journal of the American Chemical Society; (USA), Vol. 111:19; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
PIPERAZINES
CRYSTAL STRUCTURE
DIELECTRIC PROPERTIES
SYNTHESIS
CALCULATION METHODS
DATA ANALYSIS
DIMERS
EXPERIMENTAL DATA
MEASURING INSTRUMENTS
MEASURING METHODS
NONLINEAR OPTICS
PHOTOCHEMISTRY
AZINES
CHEMISTRY
DATA
ELECTRICAL PROPERTIES
HETEROCYCLIC COMPOUNDS
INFORMATION
NUMERICAL DATA
OPTICS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHYSICAL PROPERTIES
PYRAZINES
400500* - Photochemistry