Abstract In this work, we selected two benzofuranone derivatives, phthalide (PA) and coumaranone (Cmno), as the luminophores for electrochemiluminescence (ECL). During the experiments, we employed K₂S₂O₈ as the co‐reactant and observed that both compounds could generate ECL signals in K₂S₂O₈ solution. By analyzing their cyclic voltammetry curves, fluorescence spectra, and ECL spectra, among others, we speculated on the ECL mechanisms of these two systems. To further compare the differences in ECL signals between the two systems, we employed density functional theory (DFT) to calculate their molecular orbital energy levels. The results indicated that Cmno is more likely to form an excited state, producing a stronger ECL signal. This theoretical result is consistent with the results obtained from the ECL intensity–potential curves. Additionally, we discovered that 2‐dimethylaminoethanol (DMAEA) significantly quenches the ECL signal of Cmno, and this quenching depended on the concentration of DMAEA. Based on these findings, we developed a simple, sensitive, and highly selective method for detecting the concentration of DMAEA.

The carrier non-radiative recombination and instability of device caused by the inherent defects are main factors limiting development of perovskite solar cells (PSCs). During the fabrication process of a PSC device, perovskite films often produce Pb0 and I0 defects. This paper reports a strategy for synergistic optimization of perovskite films by defects passivation and surface modification. The doping of phthalide (PT) in the Pb-rich (CH(NH2 )2 )1-x (CH3 NH3 )x PbI3 film can passivate lead cation defects, and the modification of 1-iodooctadecane (1-IO) can reduce halogen anion defects and improve stability of PSCs owing to its hydrophobicity. The PT and 1-IO optimized device achieves a power conversion efficiency (PCE) of 22.27%. The optimized PSCs remain 93.2% of the initial PCE when placed in air environment (relative humidity of 10%, 25°C) more than 70 days. The PT and 1-IO synergistic optimization provides a novel strategy for improving the performance and stability of PSCs.

Abstract In general, the properties of organic molecules for persistent room‐temperature phosphorescence (p‐RTP) rely heavily on the molecular packing in aggregated state, and the molecular packing is highly related to the structure and electronic properties of molecules. Thus, through rational design of molecules, it is possible to control the packing and hence the properties of p‐RTP molecules. In this work, traditional CO is replaced by phthalide (PT) unit to achieve desired molecular packing with strong intermolecular interactions. Butterfly‐like molecules are successfully synthesized, which show bright mechanoluminescence (ML) as well as robust p‐RTP effect with phosphorescence lifetime (τp) up to 810 ms and efficiency (ΦP) of 5.1%. Compared to their contrastive carbonyl‐only molecules, two butterfly‐like molecules increase their τp from 12.1 to 810 ms and 1.3 to 396 ms, respectively. Herein, from elaborate molecular structure design to the expected packing, and then to excellent performance, new pure organic p‐RTP and ML molecules are shared for the better understanding of the molecular structure–packing–performance relationship.

A new phthalide, namely 7-methoxy-3-propylidenephthalide (1), along with two known compounds (2, 3) were isolated from the roots of the edible herb Levisticum officinale W.D.J. Koch, commonly known as lovage and well known in traditional medicine for its spasmolytic and diuretic effects. The structure of the new compound was established by HRMS and 1D & 2D NMR (1H 1H COSY, HMQC, and HMBC) spectroscopic analysis. All compounds are reported for the first time from L. officinale. Compounds 1-3 were tested against two Gram negative (Escherichia coli, Pseudomonas aeruginosa) and two Gram positive (Staphylococcus aureus and vancomycin-resistant Enterococcus [VRE] faecium) bacteria strains. Compound 3 was active against S. aureus, E. coli and vancomycin-resistant E. faecium with MIC values of 16, 64, and 128 μg/mL, respectively.

Fluorescence of Phthalide

Efficient conversion of dimethyl phthalate to phthalide over CuO in aqueous media

Ag(I)-Catalyzed Synthesis of Chiral C(3)-Functionalized Phthalides

This study was conducted to develop functional sources of herbal cosmetics for treatment of skin aging and inflammatory disorders using volatile flavor extracts of four different herbal medicinal prescriptions including Cnidium officinale Makino (COM), Angelica gigas Nakai (AGN), Mentha arvense L. (MAL), Artemisiae argyi Folium (AAF), Paeonia lactiflora Pall (PLP), Rehmanniae Radix Preparata (RRP), Scutellaria baicalensis Georgi (SBG), Panax ginseng C.A. Meyer (PGM), Glycyrrhiza uralensis Fisch (GUF). The volatile flavor extracts of four different herbal medicinal prescriptions (HH-1: COM, AGN, PLP, RRP, HH-2: COM, AGN, PLP, RRP, SBG, PGM, GUF, HH-3: COM, AGN, MAL, AAF, HH-4: COM, AGN, MAL, AAF, SBG, PGM, GUF) were extracted using SDE and their antioxidant and anti-inflammatory effects were measured by using DPPH radical and SLO, respectively. As a result, HH-2 showed moderate DPPH radical scavenging activity (68.24 %) and the strongest SLO inhibitory activity (83.96 %) at 100 μg/mL. Moreover, HH-2 of four different prescriptions significantly inhibited NO production on LPS-stimulated RAW 264.7 cells in a dose-dependent manner without considerable cell cytotoxicity at range of 2.0 ~ 50 μg/mL. Additionally, HH-2 also effectively suppressed the production of PGE2 and IL-6, which are responsible for promoting the inflammatory process. Major volatile components of HH-2 were identified as eugenol, paeonol, butyl phthalide, β-eudesmol and butylidene dihydrophthalide by GC-MS analysis. Thus, these results suggest that HH-2 may be useful as a potential source of anti-inflammatory agents in herbal medicinal cosmetics.

223 Poly(arylene ether ketone)s (PAEKs) due to a combination of excellent mechanical and thermal properties [1, 2] are widely used in industry as high strength heat resistant and thermally and chemically stable structural thermoplastics. Among them, phtha lide containing PAEKs stand out by enhanced heat resistance and unique impact elasticity [3]. Further more, such PAEKs show unusual properties promising for electronics, including the electronic switching effect under external action (for example, pressure, electric fields, etc.) [4], previously revealed for poly(diphenylenephthalide) [5]. By the example of phthalide containing PAEKs, it was shown that the structure inhomogeneity of copolymers and block copolymers of this class provides a sharp amplification of these new unusual electrophysical properties [6] typical for phthalide containing homo PAEKs. For that reason, it was expedient to develop such an approach and increase the extent of inhomogeneity of phthalide containing block copolymers by combining the blocks of polymers of different classes. Therefore, the aim of this work is to search for ways to produce phthalide containing block copolymers combining the blocks of polymers of different classes, especially polyarylates (PAr) and PAEKs.

Evaluation of the Antitoxic Effect of Phthalides from Apium graveolens in Acrylamide Intoxication I. Evolution of the Hepatic Cytolysis and Proteosynthetic Parameters in Acrylamide Intoxication on the Background of Phthalide Protection

Abstract Mixtures of the diglycidylether of bisphenol A (DGEBA) and phthalide (PT) or 3,3′‐diphthalide (DPT) were cured using ytterbium or lanthanum triflate as catalyst. The curing was studied by differential scanning calorimetry (DSC) and Fourier transform infrared in attenuated‐total‐reflection mode (FTIR/ATR). FTIR/ATR was used to monitor the competitive reactive processes and quantify the evolution of the epoxide and lactone groups. The Tg of the crosslinked materials increased when the proportion of lactone in the curing mixture decreased. The kinetics was studied with DSC experiments and isoconversional procedures. The differences in the reactivity of the systems were related to the Lewis acidity of the lanthanide salt used as initiator. The increase in the proportion of lactone leads to an increase in the reaction rate. The shrinkage was determined from the densities before and after curing and its evolution was studied by thermomechanical analysis. The materials obtained were characterized by thermogravimetry and dynamic mechanical thermal analysis. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 1711–1721, 2006

Four C-2 unsubstituted naphtho[2,3-b]furan-4,9-quinones were prepared via the corresponding phthalides obtained by directed ortho-metalation-based route.

Regiospecific 4,6-Functionalization of Pyranosides via Dimethylboron Bromide-Mediated Cleavage of Phthalide Orthoesters

Pulmonary toxicity of 2-isopropylnaphthalene (2-IPN) and its photoproducts was studied in mice. Twenty-four h after the intraperitoneal injection of 2-IPN or its photoproducts, 2-isopropenylnaphthalene (2-IPeN) (1000 mg/kg), 2-acetonaphthone (2-AN) (700 mg/kg), β-naphthol (BN) (50 mg/kg), phthalide (PH) (500 mg/kg) and phthalic acid (PA) (100 mg/kg) produced pulmonary damage, but 2-IPN (3000 mg/kg) and 2-(2-naphthyl)-2-propanol (2-NP) (1000 mg/kg) did not produce pulmonary damage. The maximum levels of 2-IPN in the lung, liver and kidney were observed 6 h after the administration, and then the levels decreased with time. The concentrations of 2-IPeN, 2-NP, 2-AN, BN, PH and PA in the tissues reached the maximum levels within 1 or 2 h, and then rapidly decreased with time. The binding of both 2-AN and BN to lung slices was greater than that of other compounds. The injections of 2-IPN, 2-IPeN, BN and PH caused considerable depletion of pulmonary GSH (reduced glutathione) at 12 h after the administration of the compounds. These results suggested that their reactive metabolites such as "epoxides" were produced and interacted with GSH. While the injection of 2-NP, 2-AN and PA did not cause depletion of pulmonary GSH. Treatment with 2-IPN and its photoproducts did not affect lipid peroxidation and phospholipid in the lung.

We describe the isolation of a new phthalide, 3-(3-hydroxypropyl)-phthalide from flowers of gentiana pedicellata Wall. (gentianaceae)

Abstract The dimethoxybenzaldehyde dimethyl acetal (I), derived from vanillin, is selectively lithiated in 2‐position and then cyclized with the aldehydes (II), producing the methoxydihydrobenzoisofurans (III).

Benz-fused Lactones. I. Synthesis of 3-Methyl-1(3H)-isobenzofuranones [Phthalides

Abstract The phthalides (I) react with p‐dimethylaminobenzaldehyde (II) to produce the indanediones (III).

Effect of water on the polymerization of methylidene phthalide

A new compound obtained from extracts of Penicilliumgladioli has been shown to be 3-ethoxy-4-hydroxymethyl-7-methoxy-6-methyl phthalide, an artifact formed from dihydrogladiolic acid during isolation.