Fulvenes and Thermochromic Ethylenes. Part 52 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their NMR and Infrared Spectra

Agranat, Israel; Loewenstein, Ruth M. J.; Bergmann, Ernst D.

doi:10.1002/ijch.196900013

Cited by 12 publications

(2 citation statements)

References 7 publications

(5 reference statements)

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“…Compounds 1a, 1d, and 1e are synthesized in analogy to the known procedure and are purified by column chromatography on silica gel and subsequent crystallization. Dichloromethane and chloroform are of analytical grade (Frutarom).…”

Section: Methodsmentioning

confidence: 99%

Langmuir and Langmuir−Blodgett Films of NLO Active 2-(p-N-Alkyl-N-methylamino)benzylidene-1,3-indandioneπ/A Curves, UV−Vis Spectra, and SHG Behavior

et al. 2001

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We study 2-(p-N-hexadecyl-N-methylamino)benzylidene-1,3-indandione (1a) as a model compound for the preparation of nonlinear optically (NLO) active Langmuir-Blodgett (LB) layers. The pressure-area (π-A) isotherm of (1a) at the air-water interface is investigated. A limiting area of 0.60 ( 0.02 nm 2 per molecule is found. The alternate-layer LB deposition of compound (1a) and an inert spacer, cadmium stearate, at different surface pressures is performed. The effects of temperature and delay time between spreading of the Langmuir film and the deposition of the LB films are studied. An increase of collapse pressure from 20 to 30 mN/m is observed as the delay time increases. UV-vis spectra indicate a uniform transfer of (1a) and show compressioninduced changes as a function of the deposition conditions. A split of the absorption maximum is observed for LB films deposited at higher pressures and lower temperatures. The two bands can result from two different molecular electronic transitions, affected by the aligning influence of the surface, and the different environments in the film compared to solution. Alternatively, these two bands can be associated with (at least) two different conformers. The orientation of the transition moments is evaluated on the basis of polarized UV-vis spectra at different angles of incidence, and found to be 40-44°. Significant second harmonic (SH) generation by the LB films is observed. Analysis of the SH response gives a tilt angle of 44°, in agreement with the finding from UV absorbance.

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Section: Methodsmentioning

confidence: 99%

Langmuir and Langmuir−Blodgett Films of NLO Active 2-(p-N-Alkyl-N-methylamino)benzylidene-1,3-indandioneπ/A Curves, UV−Vis Spectra, and SHG Behavior

et al. 2001

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“…Other known preparation procedures employ refluxing the components in acetic acid containing small amount of sulfuric acid affording the product with the melting point 204 °C (ref. 21) and heating in acetic anhydride at 60 °C, 12 the melting point 218–220 °C (from acetic anhydride). The addition of a base as a catalyst gives rise to the formation of several by-products including bindone 11 (Chart 3).…”

Section: Resultsmentioning

confidence: 99%

Conjugated donor–acceptor substituted systems involving the 1,3-indandione-derived electron accepting moieties

et al. 2022

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Fulvenes and Thermochromic Ethylenes, Part 53 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their Dipole Moments and Electronic Spectra

Weiler‐Feilchenfeld

Loewenstein

Agranat

et al. 1969

Israel Journal of Chemistry

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The molar refractions (polarizabilities) and dipole moments of fourteen 2‐arylmethylene‐1,3‐indandiones (I) and the electronic absorption spectra of twenty‐one representatives of this series have been measured. From these data certain features of the fine structure of the compounds have been deduced; inter alia, the carbonyl groups in I are bent away from the benzene ring of the indane moiety, and the 4‐dimethylaminophenyl compound II exists to a significant extent in the zwitterionic form IIA.

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Fulvenes and Thermochromic Ethylenes. Part 52 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their NMR and Infrared Spectra

Abstract: A large number of 2‐arylmethylene‐1,3‐indandiones have been prepared and their nuclear magnetic resonance and infrared spectra have been measured. The measurements have been used to elucidate some details of the fine structure of these compounds.

Cited by 12 publications

References 7 publications

Langmuir and Langmuir−Blodgett Films of NLO Active 2-(p-N-Alkyl-N-methylamino)benzylidene-1,3-indandioneπ/A Curves, UV−Vis Spectra, and SHG Behavior

Langmuir and Langmuir−Blodgett Films of NLO Active 2-(p-N-Alkyl-N-methylamino)benzylidene-1,3-indandioneπ/A Curves, UV−Vis Spectra, and SHG Behavior

Conjugated donor–acceptor substituted systems involving the 1,3-indandione-derived electron accepting moieties

Fulvenes and Thermochromic Ethylenes, Part 53 The Fine Structure of 2‐Arylmethylene‐1,3‐Indandiones; their Dipole Moments and Electronic Spectra

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