Ortho-carborane-functionalized thiazole (o-CB-Tz) and its phenyl analogue (pH-Tz) were synthesized and systematically investigated to elucidate the influence of three-dimensional boron clusters on electronic structure and antibacterial performance. Spectroscopic and photophysical studies revealed pi-pi* transitions with slight redshifted absorption and pronounced fluorescence quenching in o-CB-Tz, attributed to photoinduced electron transfer and charge-transfer character. Density functional theory and time-dependent DFT calculations demonstrated uniform stabilization of frontier molecular orbitals and enhanced electrophilicity upon ortho-carborane incorporation. Molecular docking studies against Escherichia coli and Staphylococcus aureus DNA gyrase indicated significantly improved binding affinity and reduced inhibition constants for o-CB-Tz relative to Ph-Tz. In silico ADMET and toxicity assessments predicted favorable pharmacokinetic profiles, reduced cytochrome P450 inhibition, and improved drug-likeness for the carborane derivative. In vitro antibacterial assays further confirmed the enhanced potency of o-CB-Tz. Collectively, this integrated experimental and theoretical investigation establishes clear structure-property-activity relationships and highlights ortho-carborane-functionalized thiazoles as promising platforms for the development of next-generation organoboron-based antimicrobial agents.

The development of tumor-selective boron carriers is critical for advancing targeted cancer therapies. In this study, we report the design, synthesis, and characterization of four ortho-carborane-appended symmetrical trimers, Ph-6-CB, Ph-9-CB, Tz-6-CB, and Tz-9-CB, to systematically compare the influence of central-core electronics and peripheral carborane density on photophysical and biological properties. Photophysical studies revealed that all four conjugates exhibit strong π-π* absorption in the 328-335 nm region; the triazine-cored derivatives show a modest blue shift relative to their phenylene analogs. Phenylene derivatives retain higher fluorescence quantum yields than their triazine analogs. Qualitative DFT analysis displays smaller HOMO-LUMO separations and substantially higher computed electrophilicity indices for triazine analogs than the phenylene analogs. Preliminary in vitro cytotoxicity assays against MDA-MB-231 triple-negative breast cancer cells and NIH/3T3 mouse embryo fibroblasts revealed higher potency and greater cancer selectivity of triazine derivatives than their phenylene counterparts. Tz-9-CB emerged as the lead candidate, with an IC50 of 6 µM against MDA-MB-231 cells and a selectivity index of 13 relative to NIH/3T3 fibroblasts. Mechanistic studies, including Live/Dead fluorescence imaging and caspase-3 activation assays, confirmed that Tz-9-CB induces cell death primarily through apoptosis. These findings highlight the potential of triazine-cored, carborane-rich dendrimers as selective scaffolds for boron-based cancer therapeutics.

A novel ferrocene-triazole-BODIPY conjugate (Fc-Tz-BDP) and its non-ferrocenyl analogue (Ph-Tz-BDP) were designed and synthesized via the copper(I)-catalyzed azide-alkyne cycloaddition reaction. The newly synthesized conjugates were characterized using H-1 NMR, C-13 NMR, B-11 NMR, F-19 NMR, FT-IR, and mass spectral analysis. A detailed investigation into their photophysical, electrochemical, and theoretical properties was conducted to elucidate the electronic interactions between the ferrocene and BODIPY moieties. Photophysical studies revealed that the ferrocene unit acts as a quencher of the BODIPY fluorescence, with the quantum yield being more than four times lower than that of the reference Ph-Tz-BDP due to an efficient PET mechanism. Cyclic voltammetry experiments confirmed that the HOMO is localized on the electron-donating ferrocene unit, while the LUMO resides on the BODIPY core, providing the driving force for PET. These experimental results were supported by DFT and TD-DFT calculations.

A series of carborane-appended BODIPY derivatives (compounds 4–8) were synthesized and investigated to understand the influence of carborane substitution on molecular conformation, electronic structure, and fluorescence behavior. The compounds were prepared using established synthetic routes, including Sonogashira and Suzuki cross-coupling, followed by dipyrromethane-based BODIPY formation and carborane incorporation. Density functional theory (DFT) calculations at the B3LYP/6-31G(d, p) level with solvent effects modeled via CPCM revealed that ortho- and meta-carborane substitutions (compounds 5 and 6) led to nearly planar geometries and partial delocalization of the LUMO onto adjacent phenyl rings, yet showed lower fluorescence quantum yields due to efficient photoinduced electron transfer (PET). In contrast, control compound 4 and compound 8 exhibited larger dihedral angles that disrupted π-conjugation but retained higher quantum yields, attributed to reduced PET. UV-Vis absorption and fluorescence spectra showed minimal shifts across all derivatives, with similar HOMO-LUMO gaps (2.24–2.92 eV) and emission maxima in the 563–567 nm range. The findings underscore the delicate interplay between molecular conformation and excited-state processes in determining fluorescence efficiency. Notably, the integration of boron-rich carborane clusters with optically active BODIPY scaffolds presents a promising strategy for dual-functional cancer theranostics, including boron neutron capture therapy (BNCT) and photodynamic therapy (PDT), by combining boron delivery with fluorescent imaging capabilities. Carborane substitution alters molecular geometry and orbital distribution, affecting π-conjugation and enabling photoinduced electron transfer (PET) induced quenching. Fluorescence efficiency is governed more by dihedral angles and PET effects than by conjugation extent. BODIPY-carborane hybrids are promising for dual cancer therapies, including boron neutron capture therapy (BNCT) and photodynamic therapy (PDT).

Pollution from mercury ions (Hg2+) continues to pose a significant threat to the environment and public health because of its extreme toxicity and bioaccumulative nature. BODIPY-based compounds are emerging as strong candidates for creating selective and sensitive chemosensors for mercury ion detection. Their structural tunability facilitates the introduction of various functional groups, improving their binding affinity and specificity toward mercury ions. This review elucidates various sensing mechanisms and provides comprehensive insights into the performance of these sensors, particularly with regard to selectivity, sensitivity, and detection limits. The synthetic routes for synthesizing the chemosensors are mentioned in detail. Given their reliability and flexibility, BODIPY-based sensors are poised to make significant contributions in the fields of both sensors and analytical chemistry.

The integration of s-triazine and BODIPY scaffolds has emerged as a versatile strategy for developing multifunctional conjugates with tailored photophysical and biological properties. This review provides a detailed overview of the different design principles, synthetic strategies, and applications of s-triazine BODIPY conjugates in the last decade. Key photophysical parameters such as absorption maxima, fluorescence lifetimes, quantum yields, and singlet oxygen generation efficiencies are examined in the context of their structure-property relationships. The diverse applications of the conjugates are categorized into three primary domains such as biological application, including imaging and photodynamic therapy; sensing applications with discussions about mechanisms like PET, ICT, ESIPT and FRET; and advanced material applications, including their use as molecular rotors, liquid crystals, photocatalysts for CO2 reduction, and components in solar cells and optoelectronic devices. This work underscores the growing importance of s-triazine-BODIPY conjugates as a modular platform for future innovations across materials science, analytical chemistry, and biomedical fields.

Two triazine-cored BODIPY trimers (Compounds 6 and 12) were synthesized and well characterized using H-1 NMR, C-13 NMR, B-11 NMR, F-19 NMR, FT-IR, and high-resolution mass spectral analysis. The photophysical, computational, and in vitro anticancer studies of the synthesized compounds were comprehensively evaluated along with previously reported phenylene-BODIPY trimer (Compound 1). The photophysical studies indicated that the triazine-cored BODIPY trimers exhibited a slight bathochromic shift compared to the phenylene-cored trimer. Density functional theory (DFT) calculations suggest that the order of stability of the BODIPY trimers was 1 > 6 > 12. The anticancer efficacy of the BODIPY trimers was investigated against human breast adenocarcinomas cell line MDA-MB-231 and mouse embryo fibroblast cell line NIH/3T3 through in vitro cytotoxicity assay. All the BODIPY trimers exhibited elevated cytotoxicity towards cancer cells while displaying lesser cytotoxicity towards normal cells. Compound 6 showed the highest cell death potential with an IC50 value of 27.02 mu M, which is twice higher than that of the chemotherapeutic drug cisplatin. The triazine-cored BODIPY trimers demonstrated superior cytotoxicity against cancer cells in comparison to their phenylene-cored counterparts. The enhanced cytotoxicity of the triazine-cored trimers suggests that the triazine core plays a crucial role in enhancing their therapeutic efficacy. This result underscores the potential of triazine-cored BODIPY trimers as promising anticancer agents.

A ferrocene-BODIPY dyad (Fc-BDP), where ferrocene is attached to the meso position of the BODIPY, and ferrocene-o-carborane-BODIPY triad (Fc-o-CB-BDP), where both the BODIPY and ferrocene are covalently attached to the o-carborane, have been synthesized and well-characterized. A comprehensive investigation of the photophysical, electrochemical, spectroelectrochemical, and computational properties of these compounds was carried out to elucidate the influence of o-carborane on the BODIPY-ferrocene conjugates. Detailed photophysical studies revealed a quenching of the emission intensity along with a 50% reduction in relative quantum yield upon incorporation of o-carborane. The electrochemical analysis identified an additional reduction peak in the triad, attributed to the reduction of the o-carborane moiety, which was absent in the dyad. Spectroelectrochemical studies demonstrated distinct color changes upon application of specific external potentials in the case of both the dyad and triad. Finally, DFT studies indicated that the incorporation of o-carborane led to an increased HOMO-LUMO energy gap (Delta Eg), thereby enhancing the ground-state stability of the triad.

The reduction of ketones to secondary alcohols is an essential reaction in organic chemistry and various reagents are utilized for this purpose. Herein, we have reported the reduction of ketone using decaborane in conventional as well as microwave-assisted methods in aqueous solution. Different types of aromatic ketones containing distinct functional groups were analyzed. We observed that ketones having an electron-withdrawing group showed a faster reaction rate with higher yield as compared to the ketones with electron-donating groups. Additionally, a comparison between microwave-assisted and conventional synthesis was done by evaluating the total reaction time and percentage yield. The results indicate that microwave-assisted synthesis lead to higher yields within very short reaction times.

Two carborane-functionalized thiocarbohydrazone derivatives, TCH- m -CB and TCH- p -CB, were synthesized and well-characterized. The anticancer potential of these compounds was evaluated in vitro against the MCF-7 human breast cancer cell line and NIH/3T3 mouse embryo fibroblast cell line. The cytotoxicity study shows that the meta-carborane derivative, TCH- m -CB, shows higher cytotoxicity toward cancer cells with an IC50 value of 36.96 mu M. The caspase-3 activity assays confirmed that both compounds induce cell death through apoptosis. The computational DFT studies indicated a higher HOMO-LUMO energy gap for TCH- m -CB (3.870 eV) compared to TCH- p -CB (2.811 eV), indicating a higher stability of the meta-carborane derivative, TCH- m -CB, in the ground state. The molecular docking study shows that the thiocarbohydrazone derivatives of carboranes exhibit stronger binding affinities to key cancer-related protein targets (Er alpha, Topo II alpha, and PARP-1) than the reference drug, doxorubicin. The in silico analysis of the ADMET properties of thiocarbohydrazone derivatives of carboranes also exhibits highly promising drug-like properties as compared to the reference drug doxorubicin. Overall, the results indicate that the carborane-functionalized thiocarbohydrazone derivatives have the potential to be effective anticancer agents.

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AbstractTriazine‐based molecules have emerged as promising candidates for developing selective and sensitive chemosensors for metal ion detection. Their structural tunability facilitates the introduction of a variety of functional groups, improving their binding affinity and specificity toward a variety of metal ions. This review highlights various sensing mechanisms, including colorimetric and fluorometric methods, and provides insights into the performance of these sensors in terms of sensitivity, selectivity, and detection limits. The synthetic routes for synthesizing the chemosensors are mentioned in detail. Given their reliability and flexibility, triazine‐based sensors are poised to make significant contributions in the field of both sensor and analytical chemistry.

A series of four carboranyl-BODIPY conjugates (o-CB-10, m-CB-15, Me-o-CB-28, and Me-o-CB-35) and one phenylene-BODIPY conjugate (PB-20) were synthesized. The carboranyl-BODIPY conjugates incorporate boron clusters, specifically ortho- and meta-carboranes, covalently linked to BODIPY fluorophores while the phenylene-BODIPY conjugate features a phenylene ring covalently linked to BODIPY fluorophore. The newly synthesized conjugates were characterized by 1H NMR, 13C NMR, 11B NMR, 19F NMR, FT-IR, and high-resolution mass spectral analysis. In vitro cytotoxicity of the synthesized conjugates has been evaluated against the HeLa cervical cancer cell line. The study reveals that o-CB-10 shows a maximum cell death potential at lower concentrations (12.03 mu M) and inhibited cell proliferation and migration in cancer (HeLa) cells. Additionally, flow cytometry study reveals that o-CB-10 and Me-o-CB-28 arrest the cell cycle at the S phase. The results indicate that the carboranyl-BODIPY conjugates have the potential to be effective anticancer agents.

AbstractAnion sensing plays a crucial role in areas ranging from medical diagnostics to environmental monitoring. Dipyrromethane‐based compounds offer a versatile platform for developing colorimetric and fluorescent chemosensors, owing to their structural tunability and favorable optical properties. This review provides a concise overview of current advancements in anion sensing using dipyrromethane molecular framework. We examined the diverse strategies employed in designing dipyrromethane‐based anion sensors. Emphasis is placed on the structure‐function relationships that dictate anion affinity and selectivity. Key sensing mechanisms, including visual detection, UV‐vis studies, NMR studies, and fluorescence modulation, are explored. Finally, the synthetic routes for the synthesis of chemosensors are mentioned in detail. Given the efficiency and flexibility of dipyrromethane‐based sensor, we believe that major developments are to be expected in the field of both sensor and analytical chemistry.

Fluoride ion is a vital trace element present in human body and a well-known very strong Lewis's base, its deficiency or overabundance creates severe hazards towards human health and environment. In this context, development of sensors for selective and sensitive detection of fluoride ion over other biologically competing anions is highly necessary. Coumarins, because of its unique properties like easy to derivatize, lower toxicity, high fluorescence quantum yield, large Stokes shift and excellent photo stability encouraged the researcher's worldwide for development of coumarin-based fluoride ion sensor. Herein, we described the development of coumarin based fluoride ion sensors since last two decades in an orderly manner. Most of the coumarin based receptors discussed here, selectively and sensitively detect fluoride ions based on the mechanism of fluoride ion induced hydrogen bonding/deprotonation/cleavage of any bulkier groups.

Boron-rich dendritic glycoconjugates of ortho-carborane clusters containing three to six peripheral hydrophilic glucose moieties have been found to be promising anticancer agents.

Carboranes and BODIPYs are the well known boron containing compounds. Both are relatively easy to functionalize, and small modification in their structures allow turning of their spectroscopic properties readily suggest the importance of carborane‐BODIPY conjugates. The combination of boron rich carborane and photosensitizers activatable BODIPYs have potentials for adequate boron delivery to the cancer tissues for successful cancer therapy. This review covers the most recent development of carborane‐BODIPY conjugates in space electronic energy transfer, photoinduced electron transfer, fluorescence emission and AIE behaviors, and as promising BNCT agents. Given the high potential and flexibility of this carborane‐BODIPY conjugates, we believe that major developments are to be expected in the field of both material and medicinal science.

o-Carborane-appended glycoconjugates containing multiple glucose and galactose moieties are found to be more cytotoxic towards cancer cells than normal cells.

A C-3-symmetrical star-shaped phenylene core based borondipyrromethene (BODIPY) has been synthesized and its toxicity and biocompatibility has been evaluated using a vertebrate model, zebrafish. The BODIPY has been found to absorb and emit in solution and solid state between 450 nm-700 nm. It has been found to be non toxic in adult zebrafish model up to concentration 100 mg/L. The neurobehavioral alterations and bioimaging properties of the BODIPY in zebrafish adults and embryos have also been investigated. The dose-response study of BODIPY6was carried out by light and dark preference test (LDPT) and novel tank diving test (NTDT) to observe behavioral alteration in adult zebrafish. The LDPT showed that time spent in light zone and number of transition to light zone rose up to administration of 6.8 mg/L BODIPY where as latency towards light zone remarkably decreased at concentration 6.8 mg/L. The NTDT test followed similar trend and the number of transitions and time spent in top zone increased in accordance to BODIPY treatment concentration where as latency towards top zone decreased gradually. The phenylene BODIPY was accumulated into and bound to different parts of zebrafish larvae. Our results indicate that the star shaped phenylene cored compound containing multiple BODIPY moieties exhibits no toxicity and also shows good biocompatibility and biodistribution in zebrafish and thus it may find promising biological applications.