Search Results (10)

Indane-1,3-dione is a versatile building block used in numerous applications ranging from biosensing, bioactivity, bioimaging to electronics or photopolymerization. In this review, an overview of the different chemical reactions enabling access to this scaffold but also to the most common derivatives of indane-1,3-dione are presented. Parallel to this, the different applications in which indane-1,3-dione-based structures have been used are also presented, evidencing the versatility of this structure. Full article

An efficient, mild, and green method was developed for the synthesis of indeno[1,2-b]quinoxaline derivatives via o-phenylenediamine (OPD) and 2-indanone derivatives utilizing β-cyclodextrin (β-CD) as the supramolecular catalyst. The reaction can be carried out in water and in a solid state at room temperature. β-CD can also catalyze the reaction of indan-1,2-dione with OPD with a high degree of efficiency. Compared to the reported methods, this procedure is milder, simpler, and less toxic, making it an eco-friendly alternative. In addition, the β-CD can be recovered and reused without the loss of activity. Full article

2-Arylidene-indan-1,3-done derivatives have very different properties, thanks to which they find various applications in science, medicine, and industry. Selected derivatives show antiviral, antibacterial, and anti-inflammatory activity. This paper presents a procedure for the synthesis of a series of indan-1,3-dione derivatives that present antiproliferative activity. The aim of the work was to develop a method of simple synthesis and purification, evaluate the fulfillment of the Lipiński’s and Veber’s rule, and determine the potential scope of application of the obtained series of compounds. The structure of the synthesized compounds was confirmed, and their lipophilicity was determined using experimental and computational methods. Their antiproliferative activity against selected cell lines was tested in accordance with the MTT protocol; the ability to bind to albumin was tested, and the parameters related to the toxicity of substances in silico were determined. The selected compounds which showed antiproliferative activity were strongly bound to albumin and, in most cases, met the Lipiński’s and Veber’s rule. Thus, the obtained results suggest that 2-arylidene-indan-1,3-done derivatives appear to be good candidates for drugs with a potential leading structure for further development. Full article

A series of dopant-free D-π-A structural hole-transporting materials (HTMs), named as SGT-460, SGT-461, and SGT-462, incorporating a planner-type triazatruxene (TAT) core, thieno[3,2-b]indole (TI) π-bridge and three different acceptors, 3-ethylthiazolidine-2,4-dione (ED), 3-(dicyano methylidene)indan-1-one (DI), and malononitrile (MN), were designed and synthesized for application in perovskite solar cells (PrSCs). The effect of three acceptor units in star-shaped D-π-A structured dopant-free HTMs on the photophysical and electrochemical properties and the photovoltaic performance were investigated compared to the reference HTM of 2,2′,7,7′-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9′-spirobifluorene (spiro-OMeTAD). Their highest occupied molecular orbital (HOMO) energy levels were positioned for efficient hole extraction from a MAPbCl_3−xI_x layer (5.43 eV). The hole mobility values of the HTMs without dopants were determined to be 7.59 × 10⁻⁵ cm² V⁻¹ s⁻¹, 5.13 × 10⁻⁴ cm² V⁻¹ s⁻¹, and 7.61 × 10⁻⁴ cm² V⁻¹ s⁻¹ for SGT-460-, SGT-461-, and SGT-462-based films. The glass transition temperature of all HTMs showed higher than that of the spiro-OMeTAD. As a result, the molecular engineering of a planer donor core, π-bridge, and end-capped acceptor led to good hole mobility, yielding 11.76% efficiency from SGT-462-based PrSCs, and it provides a useful insight into the synthesis of the next-generation of HTMs for PrSC application. Full article

The design of photoinitiating systems with excellent photochemical reactivities at 405nm LED is one of the obstacles to efficiently promote free radical polymerization in mild conditions (e.g., low light intensity, under air). Here, our actual search for new multicomponent photoinitiating systems at 405nm LED prompts us to develop new dyes based on push–pull structures. In the present paper, we chose two series of new dyes which possess indane-1,3-dione and 1H-cyclopenta naphthalene-1,3-dione groups as the electron-withdrawing groups, since they have the great potential to behave as sensitive and remarkable photoinitiators in vat photopolymerization/3D printing. When incorporated with a tertiary amine (ethyl dimethylaminobenzoate EDB, used as electron/hydrogen donor) and an iodonium salt (used as electron acceptor) as the three-component photoinitiating systems (PISs), and among a series of 21 dyes, 10 of them could efficiently promote the free radical photopolymerization of acrylates. Interestingly, steady state photolysis experiments revealed different behaviors of the dyes. Fluorescence experiments and free energy change calculations for redox processes were also carried out to investigate the relevant chemical mechanisms. Additionally, the formation of radicals from the investigated PISs was clearly observed by electron spin resonance (ESR) spin-trapping experiments. Finally, stereoscopic 3D patterns were successfully fabricated by the laser writing technique. In this work, the use of push–pull dyes based on the naphthalene scaffold as photoinitiators of polymerization is reported for the first time in a systematic study aiming at investigating the structure–performance relationship for irradiation carried out at 405 nm. By carefully selecting the electron donors used in the two series of push–pull dyes, novel and high-performance photoinitiating systems operating at 405 nm are thus proposed. Full article

The aldol condensation of indane-1,3-dione (ID) to give ‘bindone’ in water is catalysed by an M₈L₁₂ cubic coordination cage (H^w). The absolute rate of reaction is slow under weakly acidic conditions (pH 3–4), but in the absence of a catalyst it is undetectable. In water, the binding constant of ID in the cavity of H^w is ca. 2.4 (±1.2) × 10³ M⁻¹, giving a ∆G for the binding of −19.3 (±1.2) kJ mol⁻¹. The crystal structure of the complex revealed the presence of two molecules of the guest ID stacked inside the cavity, giving a packing coefficient of 74% as well as another molecule hydrogen-bonded to the cage’s exterior surface. We suggest that the catalysis occurs due to the stabilisation of the enolate anion of ID by the 16+ surface of the cage, which also attracts molecules of neutral ID to the surface because of its hydrophobicity. The cage, therefore, brings together neutral ID and its enolate anion via two different interactions to catalyse the reaction, which—as the control experiments show—occurs at the exterior surface of the cage and not inside the cage cavity. Full article

A series of ten push-pull chromophores comprising 1H-cyclopenta[b]naphthalene-1,3(2H)-dione as the electron-withdrawing group have been designed, synthesized, and characterized by UV-visible absorption and fluorescence spectroscopy, cyclic voltammetry and theoretical calculations. The solvatochromic behavior of the different dyes has been examined in 23 solvents and a positive solvatochromism has been found for all dyes using the Kamlet-Taft solvatochromic relationship, demonstrating the polar form to be stabilized in polar solvents. To establish the interest of this polyaromatic electron acceptor only synthesizable in a multistep procedure, a comparison with the analog series based on the benchmark indane-1,3-dione (1H-indene-1,3(2H)-dione) has been done. A significant red-shift of the intramolecular charge transfer band has been found for all dyes, at a comparable electron-donating group. Parallel to the examination of the photophysical properties of the different chromophores, a major improvement of the synthetic procedure giving access to 1H-cyclopenta[b]naphthalene-1,3(2H)-dione has been achieved. Full article

We describe the synthesis of silver loaded on zirconia and its use as an efficient catalyst for a one-pot three-component reaction to synthesize 11 indenopyrimidine derivatives, of which 7 are new compounds. The procedure involves substituted benzaldehydes, indane-1,3-dione, and guanidinium hydrochloride, with ethanol as solvent. The proposed green protocol at room temperature is simple and efficient, giving excellent yields (90–96%) in short reaction times (<30 min). The protocol works well according to the green chemistry principles with respect to high atom economy, no need for column separation, and reusability of the catalyst, which are attractive features. XRD, TEM, SEM, and BET analysis were used to characterize the catalyst materials. Full article

The first step in determining whether a fluorescent dye can be used for antibody labeling consists in collecting data on its physical interaction with the latter. In the present study, the interaction between the 2-(2-hydroxy-5-nitrobenzylidene)-1,3-indanedione (HNBID) dye and the IgG1 monoclonal mouse antibody anti-human heart fatty acid binding protein (anti-hFABP) has been investigated by fluorescence and circular dichroism spectroscopies and complementary structural results were obtained by molecular modeling. We have determined the parameters characterizing this interaction, namely the quenching and binding constants, classes of binding sites, and excited state lifetimes, and we have predicted the localization of HNBID within the Fc region of anti-hFABP. The key glycosidic and amino acid residues in anti-hFABP interacting with HNBID have also been identified. A similar systematic study was undertaken for the well-known fluorescein isothiocyanate fluorophore, for comparison purposes. Our results recommend HNBID as a valuable alternative to fluorescein isothiocyanate for use as a fluorescent probe for IgG1 antibodies. Full article

The title compound 2-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]-indane-1,3-dione (3) was synthesized in high yield by reaction of 3,5-dimethyl-1-phenyl-pyrazole-4-carbaldehyde and indane-1,3-dione in ethanol in the presence of pyridine. The structure of this new compound was confirmed by elemental analysis, IR, ¹H NMR, ¹³C NMR and GC-MS spectral analysis. Full article