Studies of Langmuir and Langmuir–Blodgett films of NLO-active amphiphilic 1,3-indanedione derivatives

Mechanical Manipulation of Archimedean Spirals of an Achiral Pyrazinacene for Chiral Assemblies

“…The surface pressure (π) versus area per molecule (A) isotherm shows a 2D liquid-expanded phase at low surface pressure followed by a liquid-condensed to solid phase transition, which collapses slightly above 60 mN m -1 (Figure 1b). [23] An inflection point is observed at 18 mN m -1 during the liquid-condensed to solid phase transition indicating that molecular orientation is likely to be surface pressure dependent. A lower limiting molecular area of 73 Å 2 compared to the geometric area of a single PA2 (≈511 Å 2 ) in energy minimized conformation (Figure S3, Supporting Information) suggests formation of aggregates at the air-water interface [24] and that molecules are positioned roughly perpendicularly at the interface.…”

Keto–Enol Tautomerism of Phenindione and Its Derivatives: An NMR and Density Functional Theory (DFT) Reinvestigation

“…As mentioned above, in DMSO the p-nitro-substituted compound 6 consists solely of the enol component. Moreover, its spectrum in the mixture of solvents does not reveal any changes with temperature, and no OH signal appears, even at 180 K. The observed dynamic process that is related to the symmetry of the 1 H and 13 C NMR spectra in DMSO-d 6 may be explained by interconversion of two equivalent enol forms due to proton exchange between the carbonyl oxygen atoms O-1 and O-3. The rate of exchange depends strongly on the ring substituents, being the highest in 6.…”

“…Reports concerning keto−enol equilibrium in 1,3-indandiones are based on the use of infrared and ultraviolet spectroscopy methods, and very little work has been done using NMR spectroscopy. Among the few studies that have been performed, a 13 C NMR study of phenindione showed that 95% of the molecules exist as diketones in chloroform, whereas 75− 80% of the molecules are enolized in DMSO. 17 In that study, 1 H NMR spectral patterns were not discussed, except for mentioning that the signals were "broad and poorly resolved".…”

“…Within this class, a major subclass comprises derivatives containing aromatic rings, such as 1,3-indandiones ( 1 ). These derivatives 1 (Scheme ) have been known for more than a century and found numerous applications as drugs (anticoagulants, analgesics, anti-inflammatory medicines), reagents in analytical and forensic chemistry (ninhydrins), dyes (including near-infrared dyes) and pigments, − semiconductors and photosemiconductors, and components of advanced materials. − Overall, about 3000 relevant papers have been published since Hantzsch proposed, in 1913, the enol 1a to be the predominant form of phenindione (2-phenyl-1,3-indandione 1 , R = Ph) in polar solvents . On the other hand, the correct structures of the products of the simplest reaction of 1 (R = H)self-condensationwere established just recently .…”

Crystal structure determination of rac-11′-(1-acetyl-1H-indazol-3-yl)-11′,11a′-dihydro-10′H,17′H-spiro[indene-2,18′-[5a,16b]methanotriindeno[1,2-b:1′,2′-d:2′′,1′′-g]oxocine]-1,3,10′,12′,17′(10a′H)-pentaone acetonitrile 1.5-solvate

“…1,3-Indandione derivatives have been known for more than a century and have found numerous applications as drugs (anticoagulants, analgesics, anti-inflammatory medicines; Eriks et al,1979), reagents in analytical and forensic chemistry (ninhydrins; Hansen & Joullié, 2005), dyes and pigments (Manukian & Mangini, 1970;Schelz, 1975;Bello et al, 1987), semiconductors and photo semiconductors (Silinsh & Taure, 1969), and components of advanced materials (Gvishi et al, 2003;Acharya et al, 2005;Lokshin et al, 2017). One of the important features of 1,3-indandione as well as its dimer bindone [2-(2,3-dihydro-3-oxo-1H-inden-1-ylidene)-1Hindene-1, 3(2H)-dione] is the ease of their self-condensation, often with the formation of complex cyclic structures (Jacob et al, 2000).…”