{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T18:52:09Z","timestamp":1740163929313,"version":"3.37.3"},"reference-count":101,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2022,11,10]],"date-time":"2022-11-10T00:00:00Z","timestamp":1668038400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2022,11,10]],"date-time":"2022-11-10T00:00:00Z","timestamp":1668038400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100005416","name":"Research Council of Norway","doi-asserted-by":"crossref","award":["324139"],"award-info":[{"award-number":["324139"]}],"id":[{"id":"10.13039\/501100005416","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/100007465","name":"UiT The Arctic University of Norway","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100007465","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Sci Rep"],"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Boron tribromide-mediated demethylation of rhenium-oxo and gold <jats:italic>meso<\/jats:italic>-tris(4-methoxyphenyl)corrole and <jats:italic>meso<\/jats:italic>-tris(3,5-dimethoxyphenylcorrole), M[T<jats:italic>p<\/jats:italic>OMePC] and M[T(3,5-OMe)PC] (M\u2009=\u2009ReO, Au), have yielded the corresponding phenol- and resorcinol-appended metallocorroles, M[T<jats:italic>p<\/jats:italic>OHPC] and M[T(3,5-OH)PC]<jats:bold>,<\/jats:bold> in good yields. The latter compounds proved insoluble in dichloromethane and chloroform but soluble in THF. The M[T(3,5-OH)PC] derivatives also proved moderately soluble in 0.05\u00a0M aqueous KOH. Unlike oxidation-prone aminophenyl-substituted corroles, the phenol- and resorcinol-appended metallocorroles could be readily handled in air without special precautions. The phenolic metallocorroles could be readily alkylated with 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl iodide (\u201cFtI\u201d) to afford the fluorous-tagged metallocorroles M[T<jats:italic>p<\/jats:italic>OFtPC] and M[T(3,5-OFt)PC] in\u2009&gt;\u200990% yields. The simplicity of the synthetic protocols promise a wide range of phenolic and fluorous-tagged porphyrin analogues with potential applications to diverse fields such as sensors, catalysis, and photodynamic therapy, among others.<\/jats:p>","DOI":"10.1038\/s41598-022-23889-0","type":"journal-article","created":{"date-parts":[[2022,11,10]],"date-time":"2022-11-10T20:06:24Z","timestamp":1668110784000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Phenol- and resorcinol-appended metallocorroles and their derivatization with fluorous tags"],"prefix":"10.1038","volume":"12","author":[{"given":"Abraham B.","family":"Alemayehu","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Abhik","family":"Ghosh","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2022,11,10]]},"reference":[{"key":"23889_CR1","doi-asserted-by":"crossref","unstructured":"Johnson, A. W., Kay, I. T. Corroles. I. Synthesis. J. Chem. Soc. 1620\u20131629 (1965).","DOI":"10.1039\/jr9650001620"},{"key":"23889_CR2","doi-asserted-by":"publisher","first-page":"731","DOI":"10.1002\/anie.199407311","volume":"33","author":"E Vogel","year":"1994","unstructured":"Vogel, E. et al. Metallocorroles with formally tetravalent iron. Angew. Chem. Int. Ed. 33, 731\u2013735 (1994).","journal-title":"Angew. Chem. Int. Ed."},{"key":"23889_CR3","doi-asserted-by":"publisher","first-page":"1427","DOI":"10.1002\/(SICI)1521-3773(19990517)38:10<1427::AID-ANIE1427>3.0.CO;2-1","volume":"38","author":"Z Gross","year":"1999","unstructured":"Gross, Z., Galili, N. & Saltsman, I. The first direct synthesis of corroles from Pyrrole. Angew. Chem. Int. Ed. 38, 1427\u20131429 (1999).","journal-title":"Angew. Chem. Int. Ed."},{"key":"23889_CR4","doi-asserted-by":"crossref","unstructured":"Paolesse, R. et. al. 5,10,15-Triphenylcorrole: a product from a modified Rothemund reaction. Chem. Comm. 1307\u20131308 (1999).","DOI":"10.1039\/a903247i"},{"key":"23889_CR5","unstructured":"Erben, C., Will, S., Kadish, K. M. Metallocorroles: Molecular structure, spectroscopy and electronic states. in The Porphyrin Handbook (eds. Kadish, K. M., Smith, K. M. & Guilard, R.) Vol. 2, Ch. 12, 303\u2013349 (Academic, San Diego, 2002)."},{"key":"23889_CR6","doi-asserted-by":"publisher","first-page":"3798","DOI":"10.1021\/acs.chemrev.6b00590","volume":"117","author":"A Ghosh","year":"2017","unstructured":"Ghosh, A. Electronic structure of corrole derivatives: Insights from molecular structures, spectroscopy, electrochemistry, and quantum chemical calculations. Chem. Rev. 117, 3798\u20133881 (2017).","journal-title":"Chem. Rev."},{"key":"23889_CR7","doi-asserted-by":"crossref","unstructured":"Natale, C. d., Gros, C. P. & Paolesse, R. Corroles at work: A small macrocycle for great applications. Chem. Soc. Rev. 51, 1277\u20131335 (2022).","DOI":"10.1039\/D1CS00662B"},{"key":"23889_CR8","doi-asserted-by":"publisher","first-page":"121","DOI":"10.1016\/j.ccr.2017.08.028","volume":"379","author":"A Mahammed","year":"2019","unstructured":"Mahammed, A. & Gross, Z. Corroles as triplet photosensitizers. Coord. Chem. Rev. 379, 121\u2013132 (2019).","journal-title":"Coord. Chem. Rev."},{"key":"23889_CR9","doi-asserted-by":"publisher","first-page":"1901","DOI":"10.1515\/pac-2020-0703","volume":"92","author":"CM Lemon","year":"2019","unstructured":"Lemon, C. M. Corrole photochemistry. Pure Appl. Chem. 92, 1901\u20131919 (2019).","journal-title":"Pure Appl. Chem."},{"key":"23889_CR10","doi-asserted-by":"publisher","first-page":"9230","DOI":"10.1021\/ja101647t","volume":"132","author":"JH Palmer","year":"2010","unstructured":"Palmer, J. H., Durrell, A. C., Gross, Z., Winkler, J. R. & Gray, H. B. Near-IR phosphorescence of Iridium(III) corroles at ambient temperature. J. Am. Chem. Soc. 132, 9230\u20139231 (2010).","journal-title":"J. Am. Chem. Soc."},{"key":"23889_CR11","doi-asserted-by":"publisher","first-page":"5822","DOI":"10.1039\/C6TC01126H","volume":"4","author":"SM Borisov","year":"2016","unstructured":"Borisov, S. M., Alemayehu, A. & Ghosh, A. Osmium-nitrido corroles as NIR indicators for oxygen sensors and triplet sensitizers for organic upconversion and singlet oxygen generation. J. Mater. Chem. C 4, 5822\u20135828 (2016).","journal-title":"J. Mater. Chem. C"},{"key":"23889_CR12","doi-asserted-by":"publisher","first-page":"10991","DOI":"10.1021\/acs.inorgchem.7b01302","volume":"56","author":"CM Lemon","year":"2017","unstructured":"Lemon, C. M., Powers, D. C., Brothers, P. J. & Nocera, D. G. Gold corroles as near-IR phosphors for oxygen sensing. Inorg. Chem. 56, 10991\u201310997 (2017).","journal-title":"Inorg. Chem."},{"key":"23889_CR13","doi-asserted-by":"publisher","first-page":"9360","DOI":"10.1021\/acsomega.8b01149","volume":"3","author":"AB Alemayehu","year":"2018","unstructured":"Alemayehu, A. B., McCormick, L. J., Gagnon, K. J., Borisov, S. M. & Ghosh, A. Stable Platinum(IV) corroles: Synthesis, molecular structure, and room-temperature near-IR phosphorescence. ACS Omega 3, 9360\u20139368 (2018).","journal-title":"ACS Omega"},{"key":"23889_CR14","doi-asserted-by":"publisher","first-page":"1166","DOI":"10.1039\/c8pp00473k","volume":"18","author":"SM Borisov","year":"2019","unstructured":"Borisov, S. M., Einrem, R. F., Alemayehu, A. B. & Ghosh, A. Ambient-temperature near-IR phosphorescence and potential applications of rhenium-oxo corroles. Photochem. Photobiol. Sci. 18, 1166\u20131170 (2019).","journal-title":"Photochem. Photobiol. Sci."},{"key":"23889_CR15","doi-asserted-by":"publisher","first-page":"7551","DOI":"10.1038\/s41598-020-64389-3","volume":"10","author":"IK Thomassen","year":"2020","unstructured":"Thomassen, I. K., McCormick-McPherson, L. J., Borisov, S. M. & Ghosh, A. Iridium corroles exhibit weak near-infrared phosphorescence but efficiently sensitize singlet oxygen formation. Sci. Rep. 10, 7551 (2020).","journal-title":"Sci. Rep."},{"key":"23889_CR16","doi-asserted-by":"crossref","unstructured":"Bonnett, R. Chemical Aspects of Photodynamic Therapy. 1\u2013324 (CRC, 2000).","DOI":"10.1201\/9781482296952"},{"key":"23889_CR17","doi-asserted-by":"publisher","first-page":"2711","DOI":"10.1021\/acs.chemrev.6b00400","volume":"117","author":"RD Teo","year":"2017","unstructured":"Teo, R. D., Hwang, J. Y., Termini, J., Gross, Z. & Gray, H. B. Fighting cancer with corroles. Chem. Rev. 117, 2711\u20132729 (2017).","journal-title":"Chem. Rev."},{"key":"23889_CR18","doi-asserted-by":"crossref","unstructured":"Pandey, R. K., Kessel, D. & Dougherty, T. J. (eds.) Handbook of photodynamic therapy : updates on recent applications of porphyrin-based compounds. 1\u2013564 (World Scientific, 2016).","DOI":"10.1142\/9774"},{"key":"23889_CR19","doi-asserted-by":"crossref","unstructured":"Lopes, S.M., Pineiro, M. & Pinho e Melo, T. M. Corroles and hexaphyrins: synthesis and application in cancer photodynamic therapy. Molecules 25, 3450 (2020).","DOI":"10.3390\/molecules25153450"},{"key":"23889_CR20","doi-asserted-by":"publisher","first-page":"4511","DOI":"10.1021\/ja00768a016","volume":"94","author":"RF Pasternack","year":"1972","unstructured":"Pasternack, R. F. et al. Aggregation of meso-substituted water-soluble porphyrins. J. Am. Chem. Soc. 94, 4511\u20134517 (1972).","journal-title":"J. Am. Chem. Soc."},{"key":"23889_CR21","unstructured":"Hambright, P. Chemistry of Water Soluble Porphyrins. in The Porphyrin Handbook (eds. Kadish, K. M., Smith, K. M. & Guilard, R.). Vol. 3, Ch. 18, 129\u2013210 (Academic, San Diego, 2000)."},{"key":"23889_CR22","doi-asserted-by":"publisher","first-page":"1364","DOI":"10.1021\/jm050893b","volume":"49","author":"M Sibrian-Vazquez","year":"2006","unstructured":"Sibrian-Vazquez, M., Jensen, T. J., Hammer, R. P. & Vicente, M. G. H. Peptide-mediated cell transport of water soluble porphyrin conjugates. J. Med. Chem. 49, 1364\u20131372 (2006).","journal-title":"J. Med. Chem."},{"key":"23889_CR23","doi-asserted-by":"publisher","first-page":"897","DOI":"10.1111\/j.1751-1097.2007.00073.x","volume":"83","author":"JM D\u0105browski","year":"2007","unstructured":"D\u0105browski, J. M. et al. Synthesis, photophysical studies and anticancer activity of a new halogenated water-soluble porphyrin. Photochem. Photobiol. 83, 897\u2013903 (2007).","journal-title":"Photochem. Photobiol."},{"key":"23889_CR24","doi-asserted-by":"publisher","first-page":"10261","DOI":"10.1021\/acs.chemrev.5b00244","volume":"115","author":"S Singh","year":"2015","unstructured":"Singh, S. et al. Glycosylated porphyrins, phthalocyanines, and other porphyrinoids for diagnostics and therapeutics. Chem. Rev. 115, 10261\u201310306 (2015).","journal-title":"Chem. Rev."},{"key":"23889_CR25","doi-asserted-by":"publisher","first-page":"980","DOI":"10.3390\/molecules22060980","volume":"22","author":"M Luciano","year":"2017","unstructured":"Luciano, M. & Br\u00fcckner, C. Modifications of porphyrins and hydroporphyrins for their solubilization in aqueous media. Molecules 22, 980 (2017).","journal-title":"Molecules"},{"key":"23889_CR26","doi-asserted-by":"publisher","first-page":"18935","DOI":"10.1021\/acsami.6b04269","volume":"8","author":"AB Alemayehu","year":"2016","unstructured":"Alemayehu, A. B. et al. Gold Tris(carboxyphenyl)corroles as multifunctional materials: Room temperature near-IR phosphorescence and applications to photodynamic therapy and dye-sensitized solar cells. ACS Appl. Mater. Interfaces 8, 18935\u201318942 (2016).","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"23889_CR27","doi-asserted-by":"publisher","first-page":"10596","DOI":"10.1021\/acsomega.0c01090","volume":"5","author":"RF Einrem","year":"2020","unstructured":"Einrem, R. F., Alemayehu, A. B., Borisov, S. M., Ghosh, A. & Gederaas, O. A. Amphiphilic rhenium-oxo corroles as a new class of sensitizers for photodynamic therapy. ACS Omega 5, 10596\u201310601 (2020).","journal-title":"ACS Omega"},{"key":"23889_CR28","doi-asserted-by":"publisher","first-page":"16683","DOI":"10.1021\/acsomega.1c02399","volume":"6","author":"IK Thomassen","year":"2021","unstructured":"Thomassen, I. K., Rasmussen, D., Einrem, R. F. & Ghosh, A. Simple, axial ligand-mediated route to water-soluble iridium corroles. ACS Omega 6, 16683\u201316687 (2021).","journal-title":"ACS Omega"},{"key":"23889_CR29","doi-asserted-by":"publisher","first-page":"72","DOI":"10.1126\/science.266.5182.72","volume":"266","author":"IT Horv\u00e1th","year":"1994","unstructured":"Horv\u00e1th, I. T. & R\u00e1bai, J. Facile catalyst separation without water: Fluorous biphase hydroformylation of olefins. Science 266, 72\u201375 (1994).","journal-title":"Science"},{"key":"23889_CR30","doi-asserted-by":"publisher","first-page":"1677","DOI":"10.1002\/(SICI)1521-3765(19990604)5:6<1677::AID-CHEM1677>3.0.CO;2-X","volume":"5","author":"RH Fish","year":"1999","unstructured":"Fish, R. H. Fluorous biphasic catalysis: A new paradigm for the separation of homogeneous catalysts from their reaction substrates and products. Chem. Eur. J. 5, 1677\u20131680 (1999).","journal-title":"Chem. Eur. J."},{"key":"23889_CR31","doi-asserted-by":"publisher","first-page":"587","DOI":"10.1016\/S0010-8545(99)00102-2","volume":"190","author":"LP Barthel-Rosa","year":"1999","unstructured":"Barthel-Rosa, L. P. & Gladysz, J. A. Chemistry in fluorous media: A user\u2019s guide to practical considerations in the application of fluorous catalysts and reagents. Coord. Chem. Rev. 190, 587\u2013605 (1999).","journal-title":"Coord. Chem. Rev."},{"key":"23889_CR32","doi-asserted-by":"publisher","first-page":"31","DOI":"10.1039\/C1CS15084G","volume":"41","author":"M Cametti","year":"2012","unstructured":"Cametti, M., Crousse, B., Metrangolo, P., Milani, R. & Resnati, G. The fluorous effect in biomolecular applications. Chem. Soc. Rev. 41, 31\u201342 (2012).","journal-title":"Chem. Soc. Rev."},{"key":"23889_CR33","doi-asserted-by":"publisher","first-page":"2169","DOI":"10.1021\/cr078380v","volume":"107","author":"IT Horvath","year":"2007","unstructured":"Horvath, I. T. & Anastas, P. T. Innovations and green chemistry. Chem. Rev. 107, 2169\u20132173 (2007).","journal-title":"Chem. Rev."},{"key":"23889_CR34","doi-asserted-by":"publisher","first-page":"13043","DOI":"10.1039\/C7CC07038A","volume":"53","author":"RA Day","year":"2017","unstructured":"Day, R. A., Estabrook, D. A., Logan, J. K. & Sletten, E. M. Fluorous photosensitizers enhance photodynamic therapy with perfluorocarbon nanoemulsions. Chem. Comm. 53, 13043\u201313046 (2017).","journal-title":"Chem. Comm."},{"key":"23889_CR35","doi-asserted-by":"publisher","first-page":"6850","DOI":"10.1021\/acs.orglett.8b02976","volume":"20","author":"MA Miller","year":"2018","unstructured":"Miller, M. A. & Sletten, E. M. A general approach to biocompatible branched fluorous tags for increased solubility in perfluorocarbon solvents. Org. Lett. 20, 6850\u20136854 (2018).","journal-title":"Org. Lett."},{"key":"23889_CR36","doi-asserted-by":"publisher","first-page":"738","DOI":"10.1021\/bc034179p","volume":"15","author":"A Mahammed","year":"2004","unstructured":"Mahammed, A., Gray, H. B., Weaver, J. J., Sorasaenee, K. & Gross, Z. Amphiphilic corroles bind tightly to human serum albumin. Bioconjug. Chem. 15, 738\u2013746 (2004).","journal-title":"Bioconjug. Chem."},{"key":"23889_CR37","doi-asserted-by":"publisher","first-page":"1585","DOI":"10.1021\/acs.bioconjchem.9b00231","volume":"30","author":"X Xue","year":"2019","unstructured":"Xue, X., Lindstrom, A. & Li, Y. Porphyrin-based nanomedicines for cancer treatment. Bioconjug. Chem. 30, 1585\u20131603 (2019).","journal-title":"Bioconjug. Chem."},{"key":"23889_CR38","doi-asserted-by":"publisher","first-page":"4964","DOI":"10.3390\/molecules25214964","volume":"25","author":"S Gomez","year":"2020","unstructured":"Gomez, S., Tsung, A. & Hu, Z. Current targets and bioconjugation strategies in photodynamic diagnosis and therapy of cancer. Molecules 25, 4964 (2020).","journal-title":"Molecules"},{"key":"23889_CR39","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2021.764137","volume":"9","author":"P Pathak","year":"2021","unstructured":"Pathak, P., Zarandi, M. A., Zhou, X. & Jayawickramarajah, J. Synthesis and applications of porphyrin-biomacromolecule conjugates. Front. Chem. 9, 764137 (2021).","journal-title":"Front. Chem."},{"key":"23889_CR40","doi-asserted-by":"publisher","first-page":"3358","DOI":"10.3390\/ijms21093358","volume":"21","author":"H Montaseri","year":"2020","unstructured":"Montaseri, H., Kruger, C. A. & Abrahamse, H. Recent advances in porphyrin-based inorganic nanoparticles for cancer treatment. Int. J. Mol. Sci. 21, 3358 (2020).","journal-title":"Int. J. Mol. Sci."},{"key":"23889_CR41","doi-asserted-by":"publisher","first-page":"1705704","DOI":"10.1002\/adma.201705704","volume":"30","author":"A Wang","year":"2018","unstructured":"Wang, A., Ye, J., Humphrey, M. G. & Zhang, C. Graphene and carbon-nanotube nanohybrids covalently functionalized by porphyrins and phthalocyanines for optoelectronic properties. Adv. Mater. 30, 1705704 (2018).","journal-title":"Adv. Mater."},{"key":"23889_CR42","doi-asserted-by":"publisher","first-page":"997","DOI":"10.3390\/nano11040997","volume":"11","author":"G Magna","year":"2021","unstructured":"Magna, G. et al. Recent advances in chemical sensors using porphyrin-carbon nanostructure hybrid materials. Nanomaterials 11, 997 (2021).","journal-title":"Nanomaterials"},{"key":"23889_CR43","doi-asserted-by":"publisher","first-page":"72","DOI":"10.1016\/j.snb.2012.09.055","volume":"187","author":"L Tortora","year":"2013","unstructured":"Tortora, L. et al. Supramolecular sensing mechanism of corrole thin films. Sens. Actuators B Chem. 187, 72\u201377 (2013).","journal-title":"Sens. Actuators B Chem."},{"key":"23889_CR44","doi-asserted-by":"publisher","first-page":"717","DOI":"10.1038\/bjc.1986.232","volume":"54","author":"MC Berenbaum","year":"1986","unstructured":"Berenbaum, M. C. et al. meso-Tetra(hydroxyphenyl)porphyrins, a new class of potent tumour photosensitisers with favourable selectivity. Br. J. Cancer 54, 717\u2013725 (1986).","journal-title":"Br. J. Cancer"},{"key":"23889_CR45","doi-asserted-by":"publisher","first-page":"277","DOI":"10.1042\/bj2610277","volume":"261","author":"R Bonnett","year":"1989","unstructured":"Bonnett, R., White, R. D., Winfield, U. J. & Berenbaum, M. C. Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumour photosensitizers. Biochem. J. 261, 277\u2013280 (1989).","journal-title":"Biochem. J."},{"key":"23889_CR46","doi-asserted-by":"publisher","first-page":"441","DOI":"10.1111\/j.1751-1097.1994.tb05062.x","volume":"59","author":"DA James","year":"1994","unstructured":"James, D. A., Arnold, D. P. & Parsons, P. G. Potency and selective toxicity of tetra(hydroxyphenyl)- and tetrakis(dihydroxyphenyl)porphyrins in human melanoma cells, with and without exposure to red light. Photochem. Photobiol. 59, 441\u2013447 (1994).","journal-title":"Photochem. Photobiol."},{"key":"23889_CR47","doi-asserted-by":"publisher","first-page":"8492","DOI":"10.1021\/ja971093w","volume":"119","author":"P Bhyrappa","year":"1997","unstructured":"Bhyrappa, P., Wilson, S. R. & Suslick, K. S. Hydrogen-bonded porphyrinic solids: Supramolecular networks of octahydroxy porphyrins. J. Am. Chem. Soc. 119, 8492\u20138502 (1997).","journal-title":"J. Am. Chem. Soc."},{"key":"23889_CR48","doi-asserted-by":"publisher","first-page":"517","DOI":"10.1002\/chem.201504307","volume":"22","author":"RF Einrem","year":"2016","unstructured":"Einrem, R. F., Gagnon, K. J., Alemayehu, A. B. & Ghosh, A. Metal-ligand misfits: Facile access to rhenium-oxo corroles by oxidative metalation. Chem. Eur. J. 22, 517\u2013520 (2016).","journal-title":"Chem. Eur. J."},{"key":"23889_CR49","doi-asserted-by":"publisher","first-page":"18747","DOI":"10.1002\/chem.201605015","volume":"22","author":"RF Einrem","year":"2016","unstructured":"Einrem, R. F. et al. Synthesis and molecular structure of 99Tc Corroles. Chem. Eur. J. 22, 18747\u201318751 (2016).","journal-title":"Chem. Eur. J."},{"key":"23889_CR50","doi-asserted-by":"publisher","first-page":"6382","DOI":"10.1021\/acs.inorgchem.0c00477","volume":"59","author":"AB Alemayehu","year":"2020","unstructured":"Alemayehu, A. B., Teat, S. J., Borisov, S. M. & Ghosh, A. Rhenium-imido corroles. Inorg. Chem. 59, 6382\u20136389 (2020).","journal-title":"Inorg. Chem."},{"key":"23889_CR51","doi-asserted-by":"publisher","first-page":"19727","DOI":"10.1038\/s41598-020-76308-7","volume":"10","author":"AB Alemayehu","year":"2020","unstructured":"Alemayehu, A. B., Einrem, R. F., McCormick-McPherson, L. J., Settineri, N. S. & Ghosh, A. Synthesis and molecular structure of perhalogenated rhenium-oxo corroles. Sci. Rep. 10, 19727 (2020).","journal-title":"Sci. Rep."},{"key":"23889_CR52","doi-asserted-by":"publisher","first-page":"8315","DOI":"10.1021\/acs.inorgchem.1c00986","volume":"60","author":"AB Alemayehu","year":"2021","unstructured":"Alemayehu, A. B., McCormick-McPherson, L. J., Conradie, J. & Ghosh, A. Rhenium corrole dimers: electrochemical insights into the nature of the metal-metal quadruple bond. Inorg. Chem. 60, 8315\u20138321 (2021).","journal-title":"Inorg. Chem."},{"key":"23889_CR53","doi-asserted-by":"publisher","first-page":"34086","DOI":"10.1039\/D1RA05525A","volume":"11","author":"RF Einrem","year":"2021","unstructured":"Einrem, R. F. et al. Regioselective formylation of rhenium-oxo and gold corroles: Substituent effects on optical spectra and redox potentials. RSC Adv. 11, 34086\u201334094 (2021).","journal-title":"RSC Adv."},{"key":"23889_CR54","doi-asserted-by":"publisher","first-page":"106","DOI":"10.1142\/S1088424611003045","volume":"15","author":"AB Alemayehu","year":"2011","unstructured":"Alemayehu, A. B. & Ghosh, A. Gold corroles. J. Porphyr. Phthalocyanines 15, 106\u2013110 (2011).","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"23889_CR55","doi-asserted-by":"publisher","first-page":"12294","DOI":"10.1002\/chem.201102348","volume":"17","author":"E Rabinovitch","year":"2011","unstructured":"Rabinovitch, E., Goldberg, I. & Gross, Z. Gold(I) and Gold(III) corroles. Chem. Eur. J. 17, 12294\u201312301 (2011).","journal-title":"Chem. Eur. J."},{"key":"23889_CR56","doi-asserted-by":"publisher","first-page":"12844","DOI":"10.1021\/ic202023r","volume":"50","author":"KE Thomas","year":"2011","unstructured":"Thomas, K. E., Alemayehu, A. B., Conradie, J., Beavers, C. & Ghosh, A. Synthesis and molecular structure of gold triarylcorroles. Inorg. Chem. 50, 12844\u201312851 (2011).","journal-title":"Inorg. Chem."},{"key":"23889_CR57","doi-asserted-by":"publisher","first-page":"2439","DOI":"10.1080\/00268976.2012.695031","volume":"110","author":"KE Thomas","year":"2012","unstructured":"Thomas, K. E., Beavers, C. M. & Ghosh, A. Molecular structure of a gold \u03b2-Octakis(trifluoromethyl)-meso-triarylcorrole: An 85\u00b0 difference in saddling dihedral relative to copper. Mol. Phys. 110, 2439\u20132444 (2012).","journal-title":"Mol. Phys."},{"key":"23889_CR58","doi-asserted-by":"publisher","first-page":"16839","DOI":"10.1002\/chem.201502150","volume":"21","author":"KE Thomas","year":"2015","unstructured":"Thomas, K. E. et al. Ligand noninnocence in coinage metal corroles: A silver knife-edge. Chem. - Eur. J. 21, 16839\u201316847 (2015).","journal-title":"Chem. - Eur. J."},{"key":"23889_CR59","doi-asserted-by":"publisher","first-page":"146","DOI":"10.1016\/j.jinorgbio.2016.06.026","volume":"162","author":"J Capar","year":"2016","unstructured":"Capar, J. et al. Demetalation of copper undecaarylcorroles: molecular structures of a free-base undecaarylisocorrole and a gold undecaarylcorrole. J. Inorg. Biochem. 162, 146\u2013153 (2016).","journal-title":"J. Inorg. Biochem."},{"key":"23889_CR60","doi-asserted-by":"publisher","first-page":"221","DOI":"10.1002\/open.201600168","volume":"6","author":"HK Norheim","year":"2017","unstructured":"Norheim, H. K., Schneider, C., Gagnon, K. J. & Ghosh, A. One-Pot Synthesis of a bis-Pocket Corrole through a 14-fold Bromination Reaction. ChemistryOpen 6, 221\u2013225 (2017).","journal-title":"ChemistryOpen"},{"key":"23889_CR61","doi-asserted-by":"publisher","first-page":"596","DOI":"10.1142\/S1088424618500815","volume":"22","author":"KE Thomas","year":"2018","unstructured":"Thomas, K. E., Gagnon, K. J., McCormick, L. J. & Ghosh, A. Molecular structure of gold 2,3,7,8,12,13,17,18-octabromo-5,10,15-tris(4\u2032-pentafluorosulfanylphenyl)corrole: Potential insights into the insolubility of gold octabromocorroles. J. Porphyr. Phthalocyanines 22, 596\u2013601 (2018).","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"23889_CR62","doi-asserted-by":"publisher","first-page":"533","DOI":"10.1039\/C9RA09228E","volume":"10","author":"KE Thomas","year":"2020","unstructured":"Thomas, K. E. et al. Gold dipyrrin-bisphenolates: A combined experimental and DFT study of metal\u2013ligand interactions. RSC Adv. 10, 533\u2013540 (2020).","journal-title":"RSC Adv."},{"key":"23889_CR63","doi-asserted-by":"publisher","first-page":"13236","DOI":"10.1039\/D2DT01959K","volume":"51","author":"K Sahu","year":"2022","unstructured":"Sahu, K. et al. NIR-emissive, singlet-oxygen\u2013sensitizing gold tetra (thiocyano) corroles. Dalton Trans. 51, 13236\u201313245 (2022).","journal-title":"Dalton Trans."},{"key":"23889_CR64","doi-asserted-by":"publisher","first-page":"1203","DOI":"10.1021\/ar200292d","volume":"45","author":"KE Thomas","year":"2012","unstructured":"Thomas, K. E., Alemayehu, A. B., Conradie, J., Beavers, C. M. & Ghosh, A. The structural chemistry of metallocorroles: Combined X-ray crystallography and quantum chemistry studies afford unique insights. Acc. Chem. Res. 45, 1203\u20131214 (2012).","journal-title":"Acc. Chem. Res."},{"key":"23889_CR65","doi-asserted-by":"publisher","first-page":"30","DOI":"10.1039\/C4DT02277G","volume":"44","author":"HL Buckley","year":"2015","unstructured":"Buckley, H. L. & Arnold, J. Recent developments in out-of-plane metallocorrole chemistry across the periodic table. Dalton Trans. 44, 30\u201336 (2015).","journal-title":"Dalton Trans."},{"key":"23889_CR66","doi-asserted-by":"publisher","first-page":"3095","DOI":"10.1021\/acs.accounts.1c00290","volume":"54","author":"AB Alemayehu","year":"2021","unstructured":"Alemayehu, A. B., Thomas, K. E., Einrem, R. F. & Ghosh, A. The story of 5d metallocorroles: From metal-ligand misfits to new building blocks for cancer phototherapeutics. Acc. Chem. Res. 54, 3095\u20133107 (2021).","journal-title":"Acc. Chem. Res."},{"key":"23889_CR67","doi-asserted-by":"publisher","first-page":"14411","DOI":"10.1002\/anie.201405890","volume":"53","author":"AB Alemayehu","year":"2014","unstructured":"Alemayehu, A. B., Gagnon, K. J., Terner, J. & Ghosh, A. Oxidative metalation as a route to size-mismatched macrocyclic complexes: Osmium corroles. Angew. Chem. Int. Ed. 53, 14411\u201314414 (2014).","journal-title":"Angew. Chem. Int. Ed."},{"key":"23889_CR68","doi-asserted-by":"publisher","first-page":"7786","DOI":"10.1021\/ja801049t","volume":"130","author":"JH Palmer","year":"2008","unstructured":"Palmer, J. H., Durrell, A. C., Gross, Z., Winkler, J. R. & Gray, H. B. Iridium corroles. J. Am. Chem. Soc. 130, 7786\u20137787 (2008).","journal-title":"J. Am. Chem. Soc."},{"key":"23889_CR69","doi-asserted-by":"publisher","first-page":"11093","DOI":"10.1039\/C4CC02548B","volume":"50","author":"AB Alemayehu","year":"2014","unstructured":"Alemayehu, A. B. et al. Platinum corroles. Chem. Comm. 50, 11093\u201311096 (2014).","journal-title":"Chem. Comm."},{"key":"23889_CR70","doi-asserted-by":"publisher","first-page":"2289","DOI":"10.1016\/0040-4020(68)88130-X","volume":"24","author":"JFW McOmie","year":"1968","unstructured":"McOmie, J. F. W., Watts, M. L. & West, D. E. Demethylation of aryl methyl ethers by boron tribromide. Tetrahedron 24, 2289\u20132292 (1968).","journal-title":"Tetrahedron"},{"key":"23889_CR71","doi-asserted-by":"crossref","unstructured":"Vickery, E.H., Pahler, L.F. & Eisenbraun, E.J. Selective O-demethylation of catechol ethers. Comparison of boron tribromide and iodotrimethylsilane. J. Org. Chem. 44, 4444\u20134446 (1979).","DOI":"10.1021\/jo01338a043"},{"key":"23889_CR72","doi-asserted-by":"publisher","first-page":"127","DOI":"10.1021\/cb3004622","volume":"8","author":"SC Karunakaran","year":"2013","unstructured":"Karunakaran, S. C. et al. In vitro demonstration of apoptosis mediated photodynamic activity and NIR nucleus imaging through a novel porphyrin. ACS Chem. Biol. 8, 127\u2013132 (2013).","journal-title":"ACS Chem. Biol."},{"key":"23889_CR73","doi-asserted-by":"publisher","first-page":"5009","DOI":"10.1021\/acs.jmedchem.8b00460","volume":"61","author":"B Marydasan","year":"2018","unstructured":"Marydasan, B. et al. In vitro and in vivo demonstration of human-ovarian-cancer necrosis through a water-soluble and near-infrared-absorbing chlorin. J. Med. Chem. 61, 5009\u20135019 (2018).","journal-title":"J. Med. Chem."},{"key":"23889_CR74","doi-asserted-by":"publisher","first-page":"1051","DOI":"10.1016\/0584-8539(94)00163-6","volume":"51","author":"BK Manna","year":"1995","unstructured":"Manna, B. K., Bera, S. C. & Rohatgi-Mukherjee, K. K. Effect of solvent and pH on the spectral characteristics of meso-tetrakis(p-hydroxyphenyl)porphyrin in dimethylformamide and dimethylformamide + water mixed solvents. Spectrochim. Acta A Mol. Biomol. Spectrosc. 51, 1051\u20131060 (1995).","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"23889_CR75","doi-asserted-by":"publisher","first-page":"10185","DOI":"10.1021\/jp048981f","volume":"108","author":"H Guo","year":"2004","unstructured":"Guo, H. et al. UV-vis spectrophotometric titrations and vibrational spectroscopic characterization of meso-(p-Hydroxyphenyl)porphyrins. J. Phys. Chem. B 108, 10185\u201310191 (2004).","journal-title":"J. Phys. Chem. B"},{"key":"23889_CR76","doi-asserted-by":"publisher","first-page":"587","DOI":"10.1021\/jp0523827","volume":"110","author":"H Guo","year":"2006","unstructured":"Guo, H. et al. Sequential Deprotonation of meso-(p-Hydroxyphenyl)porphyrins in DMF: From Hyperporphyrins to Sodium Porphyrin Complexes. J. Phys. Chem. B 110, 587\u2013594 (2006).","journal-title":"J. Phys. Chem. B"},{"key":"23889_CR77","doi-asserted-by":"publisher","first-page":"3613","DOI":"10.1021\/jp014417i","volume":"107","author":"IH Wasbotten","year":"2003","unstructured":"Wasbotten, I. H., Conradie, J. & Ghosh, A. Electronic absorption and resonance Raman signatures of hyperporphyrins and nonplanar porphyrins. J. Phys. Chem. B 107, 3613\u20133623 (2003).","journal-title":"J. Phys. Chem. B"},{"key":"23889_CR78","doi-asserted-by":"publisher","first-page":"1543","DOI":"10.1021\/jacsau.2c00255","volume":"2","author":"CC Wamser","year":"2022","unstructured":"Wamser, C. C. & Ghosh, A. The hyperporphyrin concept: A contemporary perspective. JACS Au 2, 1543\u20131560 (2022).","journal-title":"JACS Au"},{"key":"23889_CR79","doi-asserted-by":"publisher","first-page":"1009","DOI":"10.1021\/ic00254a011","volume":"26","author":"A Bettelheim","year":"1987","unstructured":"Bettelheim, A., White, B. A., Raybuck, S. A. & Murray, R. W. Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins. Inorg. Chem. 26, 1009\u20131017 (1987).","journal-title":"Inorg. Chem."},{"key":"23889_CR80","doi-asserted-by":"publisher","first-page":"7563","DOI":"10.1021\/jp910016h","volume":"114","author":"MG Walter","year":"2010","unstructured":"Walter, M. G. & Wamser, C. C. Synthesis and characterization of electropolymerized nanostructured aminophenylporphyrin films. J. Phys. Chem. C 114, 7563\u20137574 (2010).","journal-title":"J. Phys. Chem. C"},{"key":"23889_CR81","doi-asserted-by":"publisher","first-page":"6040","DOI":"10.1021\/jo400742f","volume":"78","author":"AB Rudine","year":"2013","unstructured":"Rudine, A. B., DelFatti, B. D. & Wamser, C. C. Spectroscopy of protonated tetraphenylporphyrins with amino\/carbomethoxy substituents: Hyperporphyrin effects and evidence for a monoprotonated porphyrin. J. Org. Chem. 78, 6040\u20136049 (2013).","journal-title":"J. Org. Chem."},{"key":"23889_CR82","doi-asserted-by":"publisher","first-page":"9953","DOI":"10.1021\/acs.jpca.1c06621","volume":"125","author":"J Conradie","year":"2021","unstructured":"Conradie, J., Wamser, C. C. & Ghosh, A. Understanding hyperporphyrin spectra: TDDFT calculations on diprotonated tetrakis(p-aminophenyl)porphyrin. J. Phys. Chem A 125, 9953\u20139961 (2021).","journal-title":"J. Phys. Chem A"},{"key":"23889_CR83","doi-asserted-by":"publisher","first-page":"5024","DOI":"10.1021\/acscatal.8b00876","volume":"8","author":"A Friedman","year":"2018","unstructured":"Friedman, A., Landau, L., Gonen, S., Gross, Z. & Elbaz, L. Efficient bio-inspired oxygen reduction electrocatalysis with electropolymerized cobalt corroles. ACS Catal. 8, 5024\u20135031 (2018).","journal-title":"ACS Catal."},{"key":"23889_CR84","doi-asserted-by":"publisher","first-page":"4354","DOI":"10.1002\/anie.201915569","volume":"59","author":"Y Zhao","year":"2020","unstructured":"Zhao, Y. et al. A corrole-based covalent organic framework featuring desymmetrized topology. Angew. Chem. Int. Ed. 59, 4354\u20134359 (2020).","journal-title":"Angew. Chem. Int. Ed."},{"issue":"6","key":"23889_CR85","doi-asserted-by":"publisher","first-page":"975","DOI":"10.1021\/ol048185s","volume":"7","author":"JP Collman","year":"2005","unstructured":"Collman, J. P. & Decr\u00e9au, R. A. 5, 10, 15-Tris (o-aminophenyl) corrole (TAPC) as a versatile synthon for the preparation of corrole-based hemoprotein analogs. Org. Lett. 7(6), 975\u2013978 (2005).","journal-title":"Org. Lett."},{"key":"23889_CR86","doi-asserted-by":"publisher","first-page":"9023","DOI":"10.1021\/acsomega.0c01068","volume":"5","author":"IK Thomassen","year":"2020","unstructured":"Thomassen, I. K. & Ghosh, A. Protonation-Induced Hyperporphyrin Spectra of meso-Aminophenylcorroles. ACS Omega 5, 9023\u20139030 (2020).","journal-title":"ACS Omega"},{"key":"23889_CR87","doi-asserted-by":"publisher","first-page":"1220","DOI":"10.1002\/marc.201200107","volume":"33","author":"A Aggarwal","year":"2012","unstructured":"Aggarwal, A., Singh, S., Samson, J. & Drain, C. M. Adaptive organic nanoparticles of a teflon-coated iron (III) porphyrin catalytically activate dioxygen for cyclohexene oxidation. Macromol. Rapid Commun. 33, 1220\u20131226 (2012).","journal-title":"Macromol. Rapid Commun."},{"key":"23889_CR88","doi-asserted-by":"publisher","first-page":"584","DOI":"10.1016\/j.ccr.2018.11.004","volume":"380","author":"JM Vincent","year":"2019","unstructured":"Vincent, J. M., Contel, M., Pozzi, G. & Fish, R. H. How the Horv\u00e1th paradigm, Fluorous biphasic catalysis, affected oxidation chemistry: Successes, challenges, and a sustainable future. Coord. Chem. Rev. 380, 584\u2013599 (2019).","journal-title":"Coord. Chem. Rev."},{"key":"23889_CR89","doi-asserted-by":"crossref","first-page":"1241","DOI":"10.1111\/php.13499","volume":"97","author":"An Update","year":"2021","unstructured":"Update, An. Aggarwal, A., Bhupathiraju, N. D. K., Farley, C. & Singh, S. Applications of Fluorous Porphyrinoids. Photochem. Photobiol. 97, 1241\u20131265 (2021).","journal-title":"Photochem. Photobiol."},{"key":"23889_CR90","doi-asserted-by":"crossref","unstructured":"Gryko, D.T. & Jadach, K. A Simple and versatile one-pot synthesis of meso-substituted trans-A2B-Corroles. J. Org. Chem. 66, 4267\u20134275.","DOI":"10.1021\/jo010146w"},{"key":"23889_CR91","doi-asserted-by":"publisher","first-page":"695","DOI":"10.1142\/S108842461250085X","volume":"16","author":"A Alemayehu","year":"2012","unstructured":"Alemayehu, A., Conradie, M. M. & Ghosh, A. Electronic absorption spectra of copper corroles: Unexpected substituent effects in trans-meso-A2B-triarylcorrole complexes. J. Porphyr. Phthalocyanines. 16, 695\u2013704 (2012).","journal-title":"J. Porphyr. Phthalocyanines."},{"key":"23889_CR92","doi-asserted-by":"publisher","first-page":"3589","DOI":"10.1039\/b713244c","volume":"5","author":"CS Reid","year":"2007","unstructured":"Reid, C. S., Zhang, Y. & Li, C. J. Fluorous tagging: an enabling isolation technique for indium-mediated allylation reactions in water. Org. Biomol. Chem. 5, 3589\u20133591 (2007).","journal-title":"Org. Biomol. Chem."},{"key":"23889_CR93","doi-asserted-by":"publisher","first-page":"911","DOI":"10.1039\/b820740b","volume":"11","author":"W Zhang","year":"2009","unstructured":"Zhang, W. Green chemistry aspects of fluorous techniques\u2014opportunities and challenges for small-scale organic synthesis. Green Chem. 11, 911\u2013920 (2009).","journal-title":"Green Chem."},{"key":"23889_CR94","doi-asserted-by":"publisher","first-page":"4701","DOI":"10.1039\/C5GC01345C","volume":"17","author":"AS Lo","year":"2015","unstructured":"Lo, A. S. & Horv\u00e1th, I. T. Fluorous ethers. Green Chem. 17, 4701\u20134714 (2015).","journal-title":"Green Chem."},{"key":"23889_CR95","doi-asserted-by":"publisher","first-page":"1048","DOI":"10.1039\/C6QO00115G","volume":"3","author":"CKE Law","year":"2016","unstructured":"Law, C. K. E. & Horv\u00e1th, I. T. Synthesis and applications of fluorous phosphines. Org. Chem. Front. 3, 1048\u20131062 (2016).","journal-title":"Org. Chem. Front."},{"key":"23889_CR96","doi-asserted-by":"publisher","first-page":"2517","DOI":"10.1021\/acs.chemrev.6b00361","volume":"117","author":"R Paolesse","year":"2017","unstructured":"Paolesse, R., Nardis, S., Monti, D., Stefanelli, M. & di Natale, C. Porphyrinoids for chemical sensor applications. Chem. Rev. 117, 2517\u20132583 (2017).","journal-title":"Chem. Rev."},{"key":"23889_CR97","doi-asserted-by":"publisher","DOI":"10.1016\/j.pdpdt.2020.101782","volume":"30","author":"A Qidwai","year":"2020","unstructured":"Qidwai, A. et al. Role of nanocarriers in photodynamic therapy. Photodiagnosis Photodyn. Ther. 30, 101782 (2020).","journal-title":"Photodiagnosis Photodyn. Ther."},{"key":"23889_CR98","doi-asserted-by":"publisher","DOI":"10.1016\/j.cocis.2021.101454","volume":"54","author":"RA Day","year":"2021","unstructured":"Day, R. A. & Sletten, E. M. Perfluorocarbon nanomaterials for photodynamic therapy. Curr. Opin. Colloid Interface Sci. 54, 101454 (2021).","journal-title":"Curr. Opin. Colloid Interface Sci."},{"key":"23889_CR99","doi-asserted-by":"crossref","unstructured":"Kobayashi, Y. et al. Unprecedented Asymmetric Epoxidation of Isolated Carbon\u2013Carbon Double Bonds by a Chiral Fluorous Fe (III) Salen Complex: Exploiting Fluorophilic Effect for Catalyst Design. Eur. J. Org. Chem. 2401\u20132408 (2019).","DOI":"10.1002\/ejoc.201900146"},{"key":"23889_CR100","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2020.151657","volume":"61","author":"K Ishihara","year":"2020","unstructured":"Ishihara, K. et al. A recyclable and highly stereoselective multi-fluorous proline catalyst for asymmetric aldol reactions. Tetrahedron Lett. 61, 151657 (2020).","journal-title":"Tetrahedron Lett."},{"key":"23889_CR101","doi-asserted-by":"crossref","unstructured":"Mika, L. T. & Horv\u00e1th, I. T. Fluorous Catalysis. in Green Techniques for Organic Synthesis and Medicinal Chemistry (eds. Zhang, W. & Cue, B. W., Jr.) 137\u2013184 (Wiley, New York, 2012).","DOI":"10.1002\/9780470711828.ch6"}],"container-title":["Scientific Reports"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-23889-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-23889-0","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-23889-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,11,12]],"date-time":"2022-11-12T18:07:23Z","timestamp":1668276443000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/s41598-022-23889-0"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,10]]},"references-count":101,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2022,12]]}},"alternative-id":["23889"],"URL":"https:\/\/doi.org\/10.1038\/s41598-022-23889-0","relation":{},"ISSN":["2045-2322"],"issn-type":[{"type":"electronic","value":"2045-2322"}],"subject":[],"published":{"date-parts":[[2022,11,10]]},"assertion":[{"value":"19 August 2022","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"7 November 2022","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"10 November 2022","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"The authors declare no competing interests.","order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"19256"}}