{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T03:18:02Z","timestamp":1792034282987,"version":"4.4.0"},"reference-count":91,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2024,11,5]],"date-time":"2024-11-05T00:00:00Z","timestamp":1730764800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>Icosahedral boron clusters-based BODIPY dyes represent a cutting-edge class of compounds that merge the unique properties of boron clusters with the exceptional fluorescence characteristics of BODIPY dyes. These kinds of molecules have garnered substantial interest due to their potential applications across various fields, mainly including optoelectronics, bioimaging, and potential use as boron carriers for Boron Neutron Capture Therapy (BNCT). Carborane clusters are known for their exceptional stability, rigid geometry, and 3D-aromaticity, while BODIPY dyes are renowned for their strong absorption, high fluorescence quantum yields, and photostability. The integration of carborane into BODIPY structures leverages the stability and versatility of carboranes while enhancing the photophysical properties of BODIPY-based fluorophores. This review explores the synthesis and structural diversity of boron clusters-based BODIPY dyes, highlighting how carborane incorporation can lead to significant changes in the electronic and optical properties of the dyes. We discuss the enhanced photophysical characteristics, such as red-shifted absorption and emission poperties, charge and electronic transfer effects, and improved cellular uptake, resulting from carborane substitution. The review also delves into the diverse applications of these compounds. In bioimaging, carborane-BODIPY dyes offer superior fluorescence properties and cellular internalization, making them ideal for cell tracking. In photodynamic therapy, (PDT) these dyes can act as potent photosensitizers capable of generating reactive oxygen species (ROS) for targeted cancer treatment making them excellent candidates for PDT. Additionally, their unique electronic properties make them suitable candidates for optoelectronic applications, including organic light-emitting diodes (OLEDs) and sensors. Overall, carborane-BODIPY dyes represent a versatile and promising class of materials with significant potential for innovation in scientific and technological applications. This review aims to provide a comprehensive overview of the current state of research on carborane-BODIPY dyes, highlighting their synthesis, properties, and broad application spectrum.<\/jats:p>","DOI":"10.3389\/fchem.2024.1485301","type":"journal-article","created":{"date-parts":[[2024,11,5]],"date-time":"2024-11-05T07:33:13Z","timestamp":1730791993000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":32,"title":["Carborane-based BODIPY dyes: synthesis, structural analysis, photophysics and applications"],"prefix":"10.3389","volume":"12","author":[{"given":"Javier","family":"Ord\u00f3\u00f1ez-Hern\u00e1ndez","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Giner","family":"Planas","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rosario","family":"N\u00fa\u00f1ez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2024,11,5]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"4944","DOI":"10.1039\/c2ra20219k","article-title":"The fluorine effect: photophysical properties of borondipyrromethene (Bodipy) dyes appended at the meso position with fluorinated aryl groups","volume":"2","author":"Alamiry","year":"2012","journal-title":"RSC Adv."},{"key":"B2","doi-asserted-by":"publisher","first-page":"177","DOI":"10.1080\/0144235X.2022.2096772","article-title":"Fundamental photophysical concepts and key structural factors for the design of BODIPY-based tunable lasers","volume":"41","author":"Avellanal-Zaballa","year":"2022","journal-title":"Int. Rev. Phys. Chem."},{"key":"B3","doi-asserted-by":"publisher","first-page":"22","DOI":"10.1021\/ol102701v","article-title":"Near-infrared nitrofluorene substituted aza-Boron-dipyrromethenes dyes","volume":"13","author":"Bellier","year":"2011","journal-title":"Org. Lett."},{"key":"B4","doi-asserted-by":"publisher","first-page":"15622","DOI":"10.1002\/chem.201802901","article-title":"Carborane-BODIPY dyads: new photoluminescent materials through an efficient heck coupling","volume":"24","author":"Bellomo","year":"2018","journal-title":"Chem. - A Eur. J."},{"key":"B5","doi-asserted-by":"publisher","first-page":"109644","DOI":"10.1016\/j.dyepig.2021.109644","article-title":"Red light-emitting Carborane-BODIPY dyes: synthesis and properties of visible-light tuned fluorophores with enhanced boron content","volume":"194","author":"Bellomo","year":"2021","journal-title":"Dye. Pigment."},{"key":"B6","doi-asserted-by":"publisher","first-page":"200","DOI":"10.1039\/c7qi00608j","article-title":"Synthesis and photophysical properties of a porphyrin-BODIPY dyad and a porphyrin-: O -carborane-BODIPY triad","volume":"5","author":"Berksun","year":"2018","journal-title":"Inorg. Chem. Front."},{"key":"B7","doi-asserted-by":"publisher","first-page":"745","DOI":"10.1039\/d3sd00348e","article-title":"Aggregation-induced emission-active azines for chemosensing applications: a five-year update","volume":"3","author":"Bhosle","year":"2024","journal-title":"Sensors Diagnostics"},{"key":"B9","doi-asserted-by":"publisher","first-page":"215688","DOI":"10.1016\/j.ccr.2024.215688","article-title":"Review of advances in development of fluorescent BODIPY probes (chemosensors and chemodosimeters) for cation recognition","volume":"505","author":"Bumagina","year":"2024","journal-title":"Coord. Chem. Rev."},{"key":"B10","first-page":"7813","volume-title":"Dyes: synthesis, spectroscopic, electrochemical, and structural properties","author":"Burghart","year":"1999"},{"key":"B11","doi-asserted-by":"publisher","first-page":"4575","DOI":"10.1002\/ejic.201700453","article-title":"Tetrakis{[(p\u2010dodecacarboranyl)methyl]stilbenyl}ethylene: a Luminescent Tetraphenylethylene (TPE) Core System","volume":"2017","author":"Cabrera-Gonzalez","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"B12","doi-asserted-by":"publisher","first-page":"1210","DOI":"10.3390\/molecules25051210","article-title":"Blue emitting star-shaped and octasilsesquioxane-based polyanions bearing boron clusters. Photophysical and thermal properties","volume":"25","author":"Cabrera-Gonz\u00e1lez","year":"2020","journal-title":"Molecules"},{"key":"B13","doi-asserted-by":"publisher","first-page":"13588","DOI":"10.1002\/chem.201601177","article-title":"Photoluminescence in carborane-stilbene triads: a structural, spectroscopic, and computational study","volume":"22","author":"Cabrera-Gonzalez","year":"2016","journal-title":"Chem. Eur. J."},{"key":"B14","doi-asserted-by":"publisher","first-page":"1763","DOI":"10.1021\/acs.bioconjchem.8b00204","article-title":"Fluorescent BODIPY-anionic boron cluster conjugates as potential agents for cell tracking","volume":"29","author":"Chaari","year":"","journal-title":"Bioconjug. Chem."},{"key":"B15","doi-asserted-by":"publisher","first-page":"5324","DOI":"10.1039\/c9bm00903e","article-title":"Efficient blue light emitting materials based on: M -carborane-anthracene dyads. Structure, photophysics and bioimaging studies","volume":"7","author":"Chaari","year":"2019","journal-title":"Biomater. Sci."},{"key":"B16","doi-asserted-by":"publisher","first-page":"2370","DOI":"10.1039\/D0QI00127A","article-title":"Anthracene\u2013styrene-substituted m-carborane derivatives: insights into the electronic and structural effects of substituents on photoluminescence","volume":"7","author":"Chaari","year":"2020","journal-title":"Inorg. Chem. Front."},{"key":"B17","doi-asserted-by":"publisher","first-page":"11336","DOI":"10.1039\/c8tc03741h","article-title":"Photoluminescence in: M -carborane-anthracene triads: a combined experimental and computational study","volume":"6","author":"Chaari","year":"","journal-title":"J. Mater. Chem. C"},{"key":"B18","doi-asserted-by":"publisher","first-page":"164710","DOI":"10.1063\/1.3118982","article-title":"Accurately determining single molecule trajectories of molecular motion on surfaces","volume":"130","author":"Claytor","year":"2009","journal-title":"J. Chem. Phys."},{"key":"B19","doi-asserted-by":"publisher","first-page":"1723","DOI":"10.3390\/biom13121723","article-title":"BODIPY-based molecules for biomedical applications","volume":"13","author":"Das","year":"2023","journal-title":"Biomolecules"},{"key":"B20","doi-asserted-by":"publisher","first-page":"3855","DOI":"10.1039\/d3qm00321c","article-title":"Versatile \u03c0-bridges in nonfullerene electron acceptors of organic solar cells","volume":"7","author":"Feng","year":"2023","journal-title":"Mater. Chem. Front."},{"key":"B21","doi-asserted-by":"publisher","first-page":"2091","DOI":"10.1039\/C6DT04003A","article-title":"Carborane-stilbene dyads: the influence of substituents and cluster isomers on photoluminescence properties","volume":"46","author":"Ferrer-Ugalde","year":"2017","journal-title":"Dalt. Trans."},{"key":"B22","doi-asserted-by":"publisher","first-page":"9940","DOI":"10.1002\/chem.201402396","article-title":"Fluorescence of new o-carborane compounds with different fluorophores: can it be tuned?","volume":"20","author":"Ferrer-Ugalde","year":"2014","journal-title":"Chem. - A Eur. J."},{"key":"B23","doi-asserted-by":"publisher","first-page":"544","DOI":"10.1002\/chem.201101881","article-title":"Synthesis and characterization of new fluorescent styrene-containing carborane derivatives: the singular quenching role of a phenyl substituent","volume":"18","author":"Ferrer-Ugalde","year":"2012","journal-title":"Chem. - A Eur. J."},{"key":"B25","doi-asserted-by":"publisher","first-page":"8262","DOI":"10.1021\/acs.chemrev.8b00551","article-title":"Nonclassical applications of closo-carborane anions: from main group chemistry and catalysis to energy storage","volume":"119","author":"Fisher","year":"2019","journal-title":"Chem. Rev."},{"key":"B26","doi-asserted-by":"publisher","first-page":"5770","DOI":"10.1016\/j.bmc.2013.07.017","article-title":"Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs","volume":"21","author":"Gibbs","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"B27","doi-asserted-by":"publisher","first-page":"209","DOI":"10.1016\/j.jorganchem.2015.05.009","article-title":"Synthesis and properties of a series of carboranyl-BODIPYs","volume":"798","author":"Gibbs","year":"2015","journal-title":"J. Organomet. Chem."},{"key":"B28","doi-asserted-by":"publisher","first-page":"1464","DOI":"10.1021\/ol100108r","article-title":"Synthesis of highly fluorescent BODIPY-based nanocars","volume":"12","author":"Godoy","year":"2010","journal-title":"Org. Lett."},{"key":"B29","volume-title":"Carboranes","author":"Grimes","year":"2016"},{"key":"B30","doi-asserted-by":"publisher","first-page":"1890","DOI":"10.1002\/chem.201103307","article-title":"Unsymmetrical p-carborane backbone as a linker for donor-acceptor dyads","volume":"18","author":"Hablot","year":"2012","journal-title":"Chem. - A Eur. J."},{"key":"B31","doi-asserted-by":"publisher","first-page":"444","DOI":"10.1039\/c2sc21505e","article-title":"Nanomechanical properties of molecular-scale bridges as visualised by intramolecular electronic energy transfer","volume":"4","author":"Hablot","year":"2013","journal-title":"Chem. Sci."},{"key":"B32","doi-asserted-by":"publisher","first-page":"6195","DOI":"10.1021\/cm701935n","article-title":"Syntheses and electropolymerization of carboranyl-functionalized pyrroles and thiophenes","volume":"19","author":"Hao","year":"2007","journal-title":"Chem. Mater."},{"key":"B33","doi-asserted-by":"publisher","first-page":"6611","DOI":"10.1002\/anie.201302081","article-title":"Through-space electronic energy transfer across proximal molecular dyads","volume":"52","author":"Harriman","year":"2013","journal-title":"Angew. Chem. - Int. Ed."},{"key":"B34","volume-title":"Boron: metallacarbaboranes","author":"Housecroft","year":"2011"},{"key":"B35","doi-asserted-by":"publisher","first-page":"319","DOI":"10.1142\/S1088424624300015","article-title":"Porphyrins as key components for photoinduced charge separation, solar cells, and optogenetics","volume":"28","author":"Imahori","year":"2024","journal-title":"J. Porphyr. Phthalocyanines 1088424624"},{"key":"B36","doi-asserted-by":"publisher","first-page":"5701","DOI":"10.1021\/cr2000866","article-title":"Boron in drug discovery: carboranes as unique pharmacophores in biologically active compounds","volume":"111","author":"Issa","year":"2011","journal-title":"Chem. Rev."},{"key":"B37","doi-asserted-by":"publisher","first-page":"819","DOI":"10.1135\/cccc19860819","article-title":"Chemistry of compounds with the 1-carba-closo-dodecaborane(12) framework","volume":"51","author":"Jel\u00ednek","year":"1986","journal-title":"Collect Czech Chem. Commun."},{"key":"B38","doi-asserted-by":"publisher","first-page":"765","DOI":"10.1126\/science.265.5173.765","article-title":"Excimers and exciplexes of conjugated polymers","volume":"265","author":"Jenekhe","year":"1994","journal-title":"Sci. (80-. )"},{"key":"B39","doi-asserted-by":"publisher","first-page":"9988","DOI":"10.1021\/jo201754m","article-title":"Regioselective stepwise bromination of boron dipyrromethene (BODIPY) dyes","volume":"76","author":"Jiao","year":"2011","journal-title":"J. Org. Chem."},{"key":"B40","doi-asserted-by":"publisher","first-page":"2780","DOI":"10.1039\/c4dt03123g","article-title":"BODIPY functionalized o-carborane dyads for low-energy photosensitization","volume":"44","author":"Jin","year":"2015","journal-title":"Dalt. Trans."},{"key":"B41","doi-asserted-by":"publisher","first-page":"286","DOI":"10.1016\/j.dyepig.2015.07.002","article-title":"The effect of heavy atom to two photon absorption properties and intersystem crossing mechanism in aza-boron-dipyrromethene compounds","volume":"122","author":"Karatay","year":"2015","journal-title":"Dye. Pigment."},{"key":"B42","doi-asserted-by":"publisher","first-page":"20433","DOI":"10.1021\/jp0525078","article-title":"Structural control of the photodynamics of boron-dipyrrin complexes","volume":"109","author":"Kee","year":"2005","journal-title":"J. Phys. Chem. B"},{"key":"B43","doi-asserted-by":"publisher","first-page":"351","DOI":"10.1021\/nn800798a","article-title":"Micrometer-scale translation and monitoring of individual nanocars on glass","volume":"3","author":"Khatua","year":"2009","journal-title":"Microm. Transl."},{"key":"B44","doi-asserted-by":"publisher","first-page":"3391","DOI":"10.1021\/acs.jpca.8b01539","article-title":"Photoinduced electron transfer in a BODIPY- ortho -carborane dyad investigated by time-resolved transient absorption spectroscopy","volume":"122","author":"Kim","year":"2018","journal-title":"J. Phys. Chem. A"},{"key":"B45","doi-asserted-by":"publisher","first-page":"e202300262","DOI":"10.1002\/tcr.202300262","article-title":"Design and photonics of merocyanine dyes","volume":"24","author":"Kulinich","year":"2024","journal-title":"Chem. Rec."},{"key":"B46","doi-asserted-by":"publisher","first-page":"16530","DOI":"10.1002\/chem.202002600","article-title":"Tuning the cell uptake and subcellular distribution in BODIPY\u2013carboranyl dyads: an experimental and theoretical study","volume":"26","author":"Labra-V\u00e1zquez","year":"2020","journal-title":"Chem. - A Eur. J."},{"key":"B47","doi-asserted-by":"publisher","first-page":"7738","DOI":"10.1021\/acs.jmedchem.5b01932","article-title":"Challenges and opportunities for the application of boron clusters in drug design","volume":"59","author":"Le\u015bnikowski","year":"2016","journal-title":"J. Med. Chem."},{"key":"B48","doi-asserted-by":"publisher","first-page":"5770","DOI":"10.1039\/d4cc01412j","article-title":"BODIPY-based photocages: rational design and their biomedical application","volume":"60","author":"Li","year":"2024","journal-title":"Chem. Commun."},{"key":"B49","doi-asserted-by":"publisher","first-page":"6989","DOI":"10.1021\/ja010988c","article-title":"A versatile catalyst for heck reactions of aryl chlorides and aryl bromides under mild conditions","volume":"123","author":"Littke","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"B50","doi-asserted-by":"publisher","first-page":"4891","DOI":"10.1021\/cr078381n","article-title":"BODIPY dyes and their derivatives: syntheses and spectroscopic properties","volume":"107","author":"Loudet","year":"2007","journal-title":"Chem. Rev."},{"key":"B51","doi-asserted-by":"publisher","first-page":"9481","DOI":"10.1021\/jo701400t","article-title":"Synthetic routes toward carborane-wheeled nanocars","volume":"72","author":"Morin","year":"2007","journal-title":"J. Org. Chem."},{"key":"B52","doi-asserted-by":"publisher","first-page":"1070","DOI":"10.1039\/c5cc08213g","article-title":"Boron clusters in luminescent materials","volume":"52","author":"Mukherjee","year":"2016","journal-title":"Chem. Commun."},{"key":"B53","doi-asserted-by":"publisher","first-page":"254","DOI":"10.1002\/anie.201609656","article-title":"Solid-state emission of the anthracene-o-carborane dyad from the twisted-intramolecular charge transfer in the crystalline state","volume":"56","author":"Naito","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"B54","doi-asserted-by":"publisher","first-page":"4471","DOI":"10.1039\/C9NJ00177H","article-title":"BODIPY-ortho-carborane-tetraphenylethylene triad: synthesis, characterization, and properties","volume":"43","author":"Nar","year":"2019","journal-title":"New J. Chem."},{"key":"B56","doi-asserted-by":"publisher","first-page":"1270","DOI":"10.1002\/anie.200503007","article-title":"A discrete PIIP assembly: the large influence of weak interactions on the 31P NMR spectra of phosphane\u2013diiodine complexes","volume":"45","author":"N\u00fa\u00f1ez","year":"2006","journal-title":"Angew. Chem. - Int. Ed."},{"key":"B57","doi-asserted-by":"publisher","first-page":"5147","DOI":"10.1039\/c6cs00159a","article-title":"Icosahedral boron clusters: a perfect tool for the enhancement of polymer features","volume":"45","author":"N\u00fa\u00f1ez","year":"","journal-title":"Chem. Soc. Rev."},{"key":"B58","doi-asserted-by":"publisher","first-page":"14307","DOI":"10.1021\/acs.chemrev.6b00198","article-title":"Electrochemistry and photoluminescence of icosahedral carboranes, boranes, metallacarboranes, and their derivatives","volume":"116","author":"N\u00fa\u00f1ez","year":"","journal-title":"Chem. Rev."},{"key":"B59","doi-asserted-by":"publisher","first-page":"9841","DOI":"10.1002\/anie.201916666","article-title":"Recent progress in the development of solid-state luminescent o-carboranes with stimuli responsivity","volume":"59","author":"Ochi","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"B60","doi-asserted-by":"publisher","first-page":"13538","DOI":"10.1021\/ja052091b","article-title":"Strikingly long C\u00b7\u00b7\u00b7C distances in 1,2-disubstitutedortho-carboranes and their dianions","volume":"127","author":"Oliva","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"B61","doi-asserted-by":"publisher","first-page":"270","DOI":"10.1002\/chem.202002419","article-title":"Reversibly switchable fluorescent molecular systems based on metallacarborane\u2013perylenediimide conjugates","volume":"27","author":"Parejo","year":"2021","journal-title":"Chem. - A Eur. J."},{"key":"B62","doi-asserted-by":"publisher","first-page":"884","DOI":"10.1039\/C6OB02602H","article-title":"Heck functionalization of an asymmetric aza-BODIPY core: synthesis of far-red infrared probes for bioimaging applications","volume":"15","author":"Parisotto","year":"2017","journal-title":"Org. Biomol. Chem."},{"key":"B63","doi-asserted-by":"publisher","first-page":"1332","DOI":"10.1135\/cccc19781332","article-title":"Chemistry of 9-mercapto-1,7-dicarba-closo-dodecaborane","volume":"43","author":"Plesek","year":"1978","journal-title":"Collect Czech Chem. Commun."},{"key":"B64","doi-asserted-by":"publisher","first-page":"12191","DOI":"10.1002\/anie.201407359","article-title":"\u03c0 aromaticity and three-dimensional aromaticity: two sides of the same coin","volume":"53","author":"Poater","year":"2014","journal-title":"Angew. Chem. - Int. Ed."},{"key":"B65","doi-asserted-by":"publisher","first-page":"9396","DOI":"10.1021\/jacs.0c02228","article-title":"Too persistent to give up: aromaticity in boron clusters survives radical structural changes","volume":"142","author":"Poater","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"B66","doi-asserted-by":"publisher","first-page":"765","DOI":"10.1039\/d3tc03449f","article-title":"Efficiency boost in non-doped blue organic light-emitting diodes: harnessing aggregation-induced emission - a comprehensive review","volume":"12","author":"Rana","year":"2023","journal-title":"J. Mater. Chem. C"},{"key":"B67","doi-asserted-by":"publisher","first-page":"7035","DOI":"10.1021\/cr200038x","article-title":"Carbaboranes as pharmacophores: properties, synthesis, and application strategies","volume":"111","author":"Scholz","year":"2011","journal-title":"Chem. Rev."},{"key":"B68","doi-asserted-by":"publisher","first-page":"2422","DOI":"10.1002\/asia.201402389","article-title":"Aliphatic amine discrimination by pentafluorophenyl dibromo BODIPY","volume":"9","author":"Sekhar","year":"2014","journal-title":"Chem. - Asian J."},{"key":"B69","doi-asserted-by":"publisher","first-page":"234","DOI":"10.1016\/j.jorganchem.2015.04.035","article-title":"Synthesis, characterization, and preliminary fluorescence study of a mixed-ligand bis(dicarbollyl)nickel complex bearing a tryptophan-BODIPY FRET couple","volume":"798","author":"Shlyakhtina","year":"2015","journal-title":"J. Organomet. Chem."},{"key":"B70","first-page":"147","article-title":"Borane, carborane and metallacarborane anions for stabilization of transient and highly reactive intermediates","volume-title":"Boron in organometallic chemistry","author":"Sivaev","year":"2019"},{"key":"B71","doi-asserted-by":"publisher","first-page":"1433","DOI":"10.1002\/ejic.200900003","article-title":"Polyhedral boranes for medical applications: current status and perspectives","volume":"2009","author":"Sivaev","year":"2009","journal-title":"Eur. J. Inorg. Chem."},{"key":"B72","doi-asserted-by":"publisher","first-page":"3497","DOI":"10.1039\/c9cs00197b","article-title":"New keys for old locks: carborane-containing drugs as platforms for mechanism-based therapies","volume":"48","author":"Stockmann","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"B73","doi-asserted-by":"publisher","first-page":"2432","DOI":"10.1039\/d3ee00461a","article-title":"A perspective on photoelectrochemical storage materials for coupled solar batteries","volume":"16","author":"Tan","year":"2023","journal-title":"Energy Environ. Sci."},{"key":"B74","doi-asserted-by":"publisher","first-page":"4290","DOI":"10.1002\/1521-3773(20001201)39:23<4290::AID-ANIE4290>3.0.CO;2-3","article-title":"The distinct effect of the o-carboranyl fragment: its influence on the I-I distance in R3PI2 complexes","volume":"39","author":"Teixidor","year":"2000","journal-title":"Angew. Chem. - Int. Ed."},{"key":"B75","doi-asserted-by":"publisher","first-page":"1357","DOI":"10.1002\/marc.201300368","article-title":"Luminescent polymer consisting of 9,12-linked o-carborane","volume":"34","author":"Tominaga","year":"2013","journal-title":"Macromol. Rapid Commun."},{"key":"B76","doi-asserted-by":"publisher","first-page":"624","DOI":"10.1002\/ajoc.201300280","article-title":"Control of the emission behaviors of trifunctional o-carborane dyes","volume":"3","author":"Tominaga","year":"2014","journal-title":"Asian J. Org. Chem."},{"key":"B77","doi-asserted-by":"publisher","first-page":"4589","DOI":"10.1002\/ejic.201700535","article-title":"Crystalline inclusion compounds of a palladacyclic tetraol host featuring o-carborane units","volume":"2017","author":"Tsang","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"B78","doi-asserted-by":"publisher","first-page":"9129","DOI":"10.1002\/anie.201903920","article-title":"Boron-cluster-enhanced ultralong organic phosphorescence","volume":"58","author":"Tu","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"B79","doi-asserted-by":"publisher","first-page":"2070","DOI":"10.1021\/jo035825g","article-title":"Convenient and efficient synthesis of functionalized oligopyridine ligands bearing accessory pyrromethene-BF2 fluorophores","volume":"69","author":"Ulrich","year":"2004","journal-title":"J. Org. Chem."},{"key":"B80","doi-asserted-by":"publisher","first-page":"173","DOI":"10.1016\/S0010-8545(02)00087-5","article-title":"The medicinal chemistry of carboranes","volume":"232","author":"Valliant","year":"2002","journal-title":"Coord. Chem. Rev."},{"key":"B81","doi-asserted-by":"publisher","first-page":"617","DOI":"10.4155\/fmc.13.41","article-title":"No TitleThe uniqueness of boron as a novel challenging element for drugs in pharmacology, medicine and for smart biomaterials","volume":"5","author":"Vinas","year":"2013","journal-title":"Futur. Med. Chem."},{"key":"B82","doi-asserted-by":"publisher","first-page":"473","DOI":"10.1021\/ar8002317","article-title":"Synthesis of single-molecule nanocars","volume":"42","author":"Vives","year":"2009","journal-title":"Acc. Chem. Res."},{"key":"B83","doi-asserted-by":"publisher","first-page":"5064","DOI":"10.1002\/chem.201304310","article-title":"Synthesis and transformations of 5-chloro-2,2\u2032-dipyrrins and their boron complexes, 8-chloro-BODIPYs","volume":"20","author":"Wang","year":"2014","journal-title":"Chem. - A Eur. J."},{"key":"B84","doi-asserted-by":"publisher","first-page":"3162","DOI":"10.1002\/anie.201900283","article-title":"Aggregation-induced electrochemiluminescence of carboranyl carbazoles in aqueous media","volume":"58","author":"Wei","year":"2019","journal-title":"Angew. Chem. - Int. Ed."},{"key":"B85","doi-asserted-by":"publisher","first-page":"e4621","DOI":"10.1002\/bio.4621","article-title":"Recent advances in aggregation-induced emission\u2013active type I photosensitizers with near-infrared fluorescence: from materials design to therapeutic platform fabrication","volume":"39","author":"Xie","year":"2024","journal-title":"Luminescence"},{"key":"B86","doi-asserted-by":"publisher","first-page":"2109","DOI":"10.1021\/acs.jmedchem.5b01783","article-title":"Synthesis and in vitro studies of a series of carborane-containing boron dipyrromethenes (BODIPYs)","volume":"59","author":"Xuan","year":"2016","journal-title":"J. Med. Chem."},{"key":"B87","doi-asserted-by":"publisher","first-page":"8688","DOI":"10.1039\/d3tc00171g","article-title":"Design, synthesis and functionalization of BODIPY dyes: applications in dye-sensitized solar cells (DSSCs) and photodynamic therapy (PDT)","volume":"11","author":"Yadav","year":"2023","journal-title":"J. Mater. Chem. C"},{"key":"B88","doi-asserted-by":"publisher","first-page":"116771","DOI":"10.1016\/j.trac.2022.116771","article-title":"Explorations into the meso-substituted BODIPY-based fluorescent probes for biomedical sensing and imaging","volume":"157","author":"Yan","year":"2022","journal-title":"Trac. - Trends Anal. Chem."},{"key":"B89","doi-asserted-by":"publisher","first-page":"1482","DOI":"10.1002\/anie.202012105","article-title":"Electrochemical B\u2212H nitrogenation: access to amino acid and BODIPY-labeled nido-carboranes","volume":"60","author":"Yang","year":"2021","journal-title":"Angew. Chem. - Int. Ed."},{"key":"B90","doi-asserted-by":"publisher","first-page":"4084","DOI":"10.1039\/D3OB00255A","article-title":"BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies","volume":"21","author":"Zaitsev","year":"2023","journal-title":"Org. Biomol. Chem."},{"key":"B91","doi-asserted-by":"publisher","first-page":"110711","DOI":"10.1016\/j.dyepig.2022.110711","article-title":"A straightforward approach to carborane-substituted BODIPY derivatives via nucleophilic aromatic substitution: synthesis and photodynamic properties","volume":"207","author":"Zaitsev","year":"","journal-title":"Dye. Pigment."},{"key":"B92","doi-asserted-by":"publisher","first-page":"741","DOI":"10.1142\/S1088424622500596","article-title":"Maleimide-functionalized BODIPY dyes: synthesis, structural determination and conjugation with carborane thiols","volume":"26","author":"Zaitsev","year":"","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"B93","doi-asserted-by":"publisher","first-page":"6181","DOI":"10.1002\/chem.201406550","article-title":"Synthesis of 3,8-Dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY from an asymmetric dipyrroketone and reactivity studies at the 3,5,8-positions","volume":"21","author":"Zhao","year":"2015","journal-title":"Chem. - A Eur. J."},{"key":"B94","doi-asserted-by":"publisher","first-page":"7978","DOI":"10.1039\/c0cc02656e","article-title":"Carborane-Bodipy scaffolds for through space energy transfer","volume":"46","author":"Ziessel","year":"2010","journal-title":"Chem. Commun."}],"container-title":["Frontiers in Chemistry"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2024.1485301\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,11,5]],"date-time":"2024-11-05T07:33:18Z","timestamp":1730791998000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2024.1485301\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,5]]},"references-count":91,"alternative-id":["10.3389\/fchem.2024.1485301"],"URL":"https:\/\/doi.org\/10.3389\/fchem.2024.1485301","relation":{},"ISSN":["2296-2646"],"issn-type":[{"value":"2296-2646","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,11,5]]},"article-number":"1485301"}}