Search Results (431)

Fused and spiro nitrogen-containing heterocycles play an important role as structural motifs in numerous biologically active natural products and pharmaceuticals. The review summarizes various approaches to the synthesis of three-, four-, five-, and six-membered fused and spiro heterocycles with one or two nitrogen atoms. The assembling of the titled compounds via cycloaddition, oxidative cyclization, intramolecular ring closure, and insertion of sextet intermediates—carbenes and nitrenes—is examined on a vast number of examples. Many of the reactions proceed with high regio-, stereo-, or diastereoselectivity and in excellent, up to quantitative, yield, which is of principal importance for the synthesis of chiral drug-like compounds. For most unusual and hardly predictable transformations, the mechanisms are given or referred to. Full article

In this article, an efficient and straightforward protocol for the construction of complex dispirocyclic skeletons via regioselective intramolecular Michael addition is presented. Diverse dispirocyclic compounds were synthesized under mild and transition-metal-free conditions with good to excellent yields. Most stereoisomers were conveniently separated by column chromatography, and their relative configurations were identified by single-crystal X-Ray diffraction of representative compounds. A scale-up experiment validated the practicality of this method. In an in vitro assay, some dispirocyclic compounds exhibited potent cytotoxicity with an IC₅₀ value of 10⁻⁶ mol/L. Full article

Perovskite solar cells (PSCs) leverage the exceptional photoelectric properties of perovskite materials, yet interfacial energy level mismatches limit carrier extraction efficiency. In this work, energy level alignment was exploited to reduce the charge transport barrier, which can be conducive to the transmission of photo-generated carriers and reduce the probability of electron–hole recombination. We designed a dual-transition perovskite solar cell (PSC) with the structure of FTO/TiO₂/Nb₂O₅/CH₃NH₃PbI₃/MoO₃/Spiro-OMeTAD/Au by finite element analysis methods. Compared with the pristine device (FTO/TiO₂/CH₃NH₃PbI₃/Spiro-OMeTAD/Au), the open-circuit voltage of the optimized cell increases from 0.98 V to 1.06 V. Furthermore, the design of a circular platform light-trapping structure makes up for the light loss caused by the transition at the interface. The short-circuit current density of the optimized device increases from 19.81 mA/cm² to 20.36 mA/cm², and the champion device’s power conversion efficiency (PCE) reaches 17.83%, which is an 18.47% improvement over the planar device. This model provides new insight for the optimization of perovskite devices. Full article

Mercury is a highly toxic heavy metal that poses serious threats to human health and environmental safety, highlighting the critical importance of accurate Hg²⁺ detection. In this study, a novel fluorescent probe AP was synthesized by conjugating fluorescein, serving as the luminescent group, with pyridine-2-carboxaldehyde to enable selective Hg²⁺ detection. Hg²⁺ binds to AP in a 1:2 stoichiometric ratio, inducing the opening of the spiro-lactam ring and resulting in a significant fluorescence enhancement. The probe exhibited excellent selectivity and sensitivity toward Hg²⁺. A strong linear correlation was observed between its fluorescence intensity and Hg²⁺ concentration (R² = 0.99952), with a detection limit of as low as 9.75 × 10⁻⁸ mol/L. The average recoveries of Hg²⁺ across various water matrices ranged from 95.23% to 103.40%, with relative standard deviations (RSDs) below 3.07%. These results indicate that the probe performs effectively in real water-sample testing. Full article

In this study, a UVC photodetector (PD) was fabricated by incorporating CsI into a conventional double-cation perovskite (FAMAPbI₃) to enhance its stability. The device utilized a methylammonium iodide post-treatment solution to fabricate CsFAMAPbI₃ perovskite thin films, which functioned as the primary light-absorbing layer in an NIP structure composed of n-type SnO₂ and p-type spiro-OMeTAD. Perovskite films were fabricated and analyzed as a function of the Cs concentration to optimize the Cs content. The results demonstrated that Cs doping improved the crystallinity and phase stability of the films, leading to their enhanced electron mobility and photodetection performance. The UVC PD with an optimum Cs concentration exhibited a responsivity of 58.2 mA/W and a detectivity of 3.52 × 10¹⁴ Jones, representing an approximately 7% improvement over conventional structures. Full article

This study reports an improved diastereoselective synthesis of substituted spiro[chromane-2,4′-pyrimidin]-2′(3′H)-ones via the acid-catalyzed condensation of 6-styryl-4-aryldihydropyrimidin-2-ones with resorcinol, 2-methylresorcinol, and pyrogallol. The optimized method allows for the isolation of diastereomerically pure products, with stereoselectivity controlled by varying acid catalysts (e.g., methanesulfonic acid vs. toluenesulfonic acid) and solvent conditions. The synthesized compounds were evaluated for antimicrobial and antioxidant activities. Notably, the (2S*,4R*,6′R*)-diastereomers exhibited significant antibacterial activity against both Gram-positive and Gram-negative bacterial strains with minimal inhibition concentration down to 2 µg/mL, while derivatives containing vicinal bisphenol moieties demonstrated potent antioxidant activity, with IC₅₀ values (12.5 µg/mL) comparable to ascorbic acid. Pharmacokinetic analysis of selected hit compounds revealed favorable drug-like properties, including high gastrointestinal absorption and blood-brain barrier permeability. These findings highlight the potential of spirochromane-pyrimidine hybrids as promising candidates for further development in the treatment of infectious diseases and oxidative stress-related pathologies. Full article

Perovskite solar cells (PSCs) have already been reported as a promising alternative to traditional energy sources due to their excellent power conversion efficiency, affordability, and versatility, which is particularly relevant considering the growing worldwide demand for energy and increasing scarcity of natural resources. However, operational concerns under environmental stresses hinder its economic feasibility. Through the addition of cesium (Cs), this study investigates how to optimize perovskite solar cells (PSCs) based on methylammonium lead-iodide (MAPbI₃) by creating mixed-cation compositions of MA_1−xCs_xPbI₃ (x = 0, 0.25, 0.5, 0.75, 1) for devices A to E, respectively. The impact of cesium content on the following factors, such as open-circuit voltage (V_oc), short-circuit current density (J_sc), fill factor (FF), and power conversion efficiency (PCE), was investigated using simulation software, with ITO/TiO₂/MA_1−xCs_xPbI₃/Spiro-OMeTAD/Au as a device architecture. Due to diminished defect density, the device with x = 0.5 (MA_0.5Cs_0.5PbI₃) attains a maximum power conversion efficiency of 18.53%, with a V_oc of 0.9238 V, J_sc of 24.22 mA/cm², and a fill factor of 82.81%. The optimal doping density of TiO₂ is approximately 10²⁰ cm⁻³, while the optimal thicknesses of the electron transport layer (TiO₂, 10–30 nm), the hole-transport layer (Spiro-OMeTAD, about 10–20 nm), and the perovskite absorber (750 nm) were identified to maximize efficiency. The inclusion of a small amount of Cs may improve photovoltaic responses; however, at elevated concentrations (x > 0.5), power conversion efficiency (PCE) diminished due to the presence of trap states. The results show that mixed-cation perovskite solar cells can be a great commercially viable option because they strike a good balance between efficiency and performance. Full article

Flexible perovskite solar cells (FPSCs) hold great promise for lightweight and wearable photovoltaics, but improving their efficiency and durability under mechanical stress remains a key challenge. In this work, we fabricate and characterize flexible planar FPSCs on a polyethylene terephthalate (PET). A phenethylammonium iodide (PEAI) surface passivation layer is introduced on the perovskite to form a two-dimensional capping layer, and its impact on device performance and stability is systematically studied. The champion PEAI-passivated flexible device achieves a power conversion efficiency (PCE) of ~16–17%, compared to ~14% for the control device without PEAI. The improvement is primarily due to an increased open-circuit voltage and fill factor, reflecting effective surface defect passivation and improved charge carrier dynamics. Importantly, mechanical bending tests demonstrate robust flexibility: the PEAI-passivated cells retain ~85–90% of their initial efficiency after 700 bending cycles (radius ~5 mm), significantly higher than the ~70% retention of unpassivated cells. This work showcases that integrating a PEAI surface treatment with optimized electron (SnO₂) and hole (spiro-OMeTAD) transport layers (ETL and HTL) can simultaneously enhance the efficiency and mechanical durability of FPSCs. These findings pave the way for more reliable and high-performance flexible solar cells for wearable and portable energy applications. Full article

Organic nonvolatile transistor memories (ONVMs) using a hybrid spiro [fluorene-9,7′-dibenzo [c, h] acridine]-5′-one (SFDBAO)/polystyrene (PS) film as bulk-heterojunction-like tunneling and trapping elements were fabricated. From the characterization of the 10% SFDBAO/PS based on ONVM, a sterically hindered small-molecule SFDBAO with rigid orthogonal configuration and a donor–acceptor (D-A) structure as a molecular-scale charge storage element demonstrated significantly higher charge trapping ability than other small-molecule materials such as C₆₀ and Alq₃. The ONVM based on 10% SFDBAO/PS presents ambipolar memory behaviors with a wide memory window (146 V), a fast-switching speed (20 ms), an excellent retention time (over 5 × 10⁴ s), and stable reversibility (36 cycles without any noticeable decay). By applying different gate voltages, the above ONVM shows reliable four-level data storage characteristics. The investigation demonstrates that the strategical bulk-heterojunction-like tunneling and trapping elements composed of small-molecule materials and polymers exhibit promising potential for high-performance ambipolar ONVMs. Full article

This study presents colorless polyimides (PIs) suitable for use as plastic substrates in flexible displays, designed to be compatible with controlled soft adhesion and easy delamination (temporary adhesion) processes. For this purpose, we focused on a PI system derived from norbornane-2-spiro-α-cyclopentanone-α′-spiro-2″-norbornane-5,5″,6,6″-tetracarboxylic dianhydride (CpODA) and 2,2′-bis(trifluoromethyl)benzidine (TFMB). This system was selected with the aim of exhibiting excellent optical transparency and low linear coefficient of thermal expansion (CTE) properties. However, fabricating this PI film via the conventional two-step process was challenging because of crack formation. In contrast, modified one-pot polymerization at 200 °C using a combined catalyst resulted in a homogeneous solution of PI with an exceptionally high molecular weight, yielding a flexible cast film. The solubility of PI plays a crucial role in its success. This study delves into the mechanism behind the significant catalytic effect on enhancing molecular weight. The CpODA/TFMB PI cast film simultaneously achieved very high optical transparency, an extremely high glass transition temperature (T_g = 411 °C), a significantly low linear coefficient of thermal expansion (CTE = 16.7 ppm/K), and sufficient film toughness, despite the trade-off between low CTE and high film toughness. The CpODA/TFMB system was modified by copolymerization with minor contents of another cycloaliphatic tetracarboxylic dianhydride, 5,5′-(1,4-phenylene)-exo-bis(hexahydro-4,7-methanoisobenzofuran-cis-exo-1,3-dione) (BzDAxx). This approach was effective in improving the film toughness without sacrificing the low CTE and other target properties. The peel strengths (σ_peel) of laminates comprising surface-modified glass substrates and various colorless PI films were measured to evaluate the compatibility with the temporary adhesion process. Most colorless PI films studied were found to be incompatible. Additionally, no correlation between σ_peel and PI structure was observed, making it challenging to identify the structural factors influencing σ_peel control. Surprisingly, a strong correlation was observed between σ_peel and CTE of the PI films, suggesting that the observed solid–solid lamination is closely linked to the unexpectedly high surface mobility of the PI films. The laminate using CpODA(90);BzDAxx(10)/TFMB copolymer exhibited suitable adhesion strength for the temporary adhesion process, while meeting other target properties. The modified one-pot polymerization method significantly contributed to the development of colorless PIs suitable for plastic substrates. Full article

Target compound 3′H-spiro[dibenzo[c,h]xanthene-7,1′-isobenzofuran]-3′-one (1) has long been known to be a by-product obtained from the preparation of naphtholphthalein. The structure of compound 1 was elucidated in the early 20th century; however, this compound has not previously been fully characterized using modern techniques. In this report, ¹H NMR and ¹³C NMR spectra are provided. X-ray crystallography is also used to characterize the title compound for the first time. Full article

Chlorella vulgaris, a unicellular microalga with broad industrial applications, is a valuable source of bioactive compounds, including proteins, pigments, and lipids. However, optimizing its growth and metabolite production remains a challenge. This study investigates the potential of angular 6/6/5/6-annelated pyrrolidine-2,3-diones—structurally complex small molecules resembling alkaloids and 13(14 → 8)abeo-steroids—as novel growth stimulants for C. vulgaris. A series of these compounds (20 structurally diverse derivatives, including 7 previously unreported ones) were synthesized and screened for their ability to enhance microalgal growth. Primary screening identified one compound as a promising candidate, significantly increasing algae cell concentration in microplate cultures. Subsequent validation in flask-scale experiments revealed that this candidate induced a 19% increase in protein content at 1 μmol/L, suggesting potential for protein enrichment in algal biomass. Stability studies of the candidate compound revealed its significant hydrolytic degradation in aqueous media. These findings highlight the potential of angular 6/6/5/6-annelated pyrrolidine-2,3-diones as modulators of microalgal metabolism, offering a new avenue for enhancing C. vulgaris biomass quality, particularly for protein-rich applications in the food and feed industries. Full article

Barium stannate (BaSnO₃) has emerged as a promising alternative electron transport material owing to its superior electron mobility, resistance to UV degradation, and energy bandgap tunability, yet BaSnO₃-based perovskite solar cells have not reached the efficiency levels of TiO₂-based designs. This theoretical study presents a design-driven evaluation of BaSnO₃-based perovskite solar cell architectures, incorporating MAPbI₃ or FAMAPbI₃ perovskite materials, Spiro-OMeTAD, or Cu₂O hole transport materials as well as hole-free configurations, under varying light intensity. Using a systematic device modelling approach, we explore the influence of key design variables—such as layer thickness, donor density, and interface defect concentration—of BaSnO₃ and operating temperature on the power conversion efficiency (PCE). Among the proposed designs, the FTO/BaSnO₃/FAMAPbI₃/Cu₂O/Au heterostructure exhibits an exceptionally effective arrangement with PCE of 38.2% under concentrated light (10,000 W/m², or 10 Sun). The structure also demonstrates strong thermal robustness up to 400 K, with a low temperature coefficient of −0.078% K⁻¹. These results underscore the importance of material and structural optimisation in PSC design and highlight the role of high-mobility, thermally stable inorganic transport layers—BaSnO₃ as the electron transport material (ETM) and Cu₂O as the hole transport material (HTM)—in enabling efficient and stable photovoltaic performance under high irradiance. The study contributes valuable insights into the rational design of high-performance PSCs for emerging solar technologies. Full article

Photodetectors are critical components in modern optoelectronic systems due to their extensive applications in information conversion and image storage. Selenium (Se), an element with a low melting point, a broad spectral response, and rapid response speed, exhibits a disadvantage of high optical reflectivity, which leads to a reduction in response. Spiro-MeOTAD, featuring controllable energy bands and facile processing, has its practical application limited by inadequate thermal and environmental stability. In this study, Spiro-MeOTAD-1 with enhanced stability was prepared through the optimization of dopants (Zn(TFSI)₂ and CNT:TiO₂) within Spiro-MeOTAD, to create a Se-F/Spiro-MeOTAD-1 heterojunction photodetector by subsequently compositing with selenium foam (Se-F). The self-powered device demonstrates exceptional photovoltaic performance within the wavelength range of 350–800 nm at 0 V bias, exhibiting a maximum responsivity of 108 mA W⁻¹, a switching ratio of 5 × 10³, a specific detectivity of 2.96 × 10¹² Jones, and a response time of 20 ms/50 ms. The device also demonstrates elevated environmental stability pretreatment at 140 °C following a one-month period. The photodetection stability of the Se-F/Spiro-MeOTAD-1 flexible PD was demonstrated by its capacity to retain 76.3% of its initial light current when subjected to 70 bending cycles at 30°. This finding further substantiates the photodetection stability of the material under various bending conditions. Further verification of the applicability of Spiro-MeOTAD-1 in Se-based devices establishes a novel paradigm for designing photodetectors with enhanced performance and stability. Full article

Five boron-centered spiro compounds with imidazo[1,5-a]pyridin-3-yl phenols as ligands were synthesized and thoroughly characterized through ¹H-NMR, ¹³C-NMR, infrared spectroscopy, and X-ray single crystal analysis. The fluorescence properties of these compounds in solution and in the solid state were investigated, revealing blue emission with wavelengths maxima dependent on the electronic properties of the substituents on the ligands in solution, and an orange-red emission in the solid state. Time-Dependent Density Functional Theory (TD-DFT) calculations were performed to describe the nature of the transitions Full article