Photochemical Formation of Anthracene Quinone Methide Derivatives

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dc.contributor.authorSkalamera, Dani
dc.contributor.authorMlinaric-Majerski, Kata
dc.contributor.authorMartin Kleiner, Irena
dc.contributor.authorKralj, Marijeta
dc.contributor.authorOake, Jessy
dc.contributor.authorWan, Peter
dc.contributor.authorBohne, Cornelia
dc.contributor.authorBasaric, Nikola
dc.date.accessioned2020-08-21T23:54:02Z
dc.date.available2020-08-21T23:54:02Z
dc.date.copyright2017en_US
dc.date.issued2017
dc.description.abstractAnthrols 2–7 were synthesized and their photochemical reactivity investigated by irradiations in aq CH3OH. Upon excitation with visible light (λ > 400 nm) in methanolic solutions, they undergo photodehydration or photodeamination and deliver methyl ethers, most probably via quinone methides (QMs), with methanolysis quantum efficiencies ΦR = 0.02–0.3. Photophysical properties of 2–7 were determined by steady-state fluorescence and time-correlated single photon counting. Generally, anthrols 2–7 are highly fluorescent in aprotic solvents (ΦF = 0.5–0.9), whereas in aqueous solutions the fluorescence is quenched due to excited-state proton transfer (ESPT) to solvent. The exception is amine 4 that undergoes excited-state intramolecular proton transfer (ESIPT) in neat CH3CN where photodeamination is probably coupled to ESIPT. Photodehydration may take place via ESIPT (or ESPT) that is coupled to dehydration or via a hitherto undisclosed pathway that involves photoionization and deprotonation of radical cation, followed by homolytic cleavage of the alcohol OH group from the phenoxyl radical. QMs were detected by laser flash photolysis and their reactivity with nucleophiles investigated. Biological investigation of 2–5 on human cancer cell lines showed enhancement of antiproliferative effect upon exposure of cells to irradiation by visible light, probably due to formation of electrophilic species such as QMs.en_US
dc.description.reviewstatusRevieweden_US
dc.description.scholarlevelFacultyen_US
dc.description.sponsorshipThese materials are based on work financed by the Croatian Foundation for Science (HRZZ IP-2014-09-6312 and IP-11-2013-5660), the Natural Sciences and Engineering Research Council of Canada (NSERC- RGPIN-121389-2012), and the University of Victoria (UVIC).en_US
dc.identifier.citationSkalamera, D., Mlinaric-Majerski, K., Martin Kleiner, I., Kralj, M., Oake, J., Wan, P., Bohne, C., & Basaric, N. (2017). Photochemical Formation of Anthracene Quinone Methide Derivatives. Journal of Organic Chemistry, 82(12), 6006-6021. https://doi.org/10.1021/acs.joc.6b02735.en_US
dc.identifier.urihttps://doi.org/10.1021/acs.joc.6b02735
dc.identifier.urihttp://hdl.handle.net/1828/12012
dc.language.isoenen_US
dc.publisherJournal of Organic Chemistryen_US
dc.subjectHydrocarbons
dc.subjectAromatic compounds
dc.subjectSolution chemistry
dc.subjectFluorescence
dc.subjectIrradiation
dc.subject.departmentDepartment of Chemistry
dc.titlePhotochemical Formation of Anthracene Quinone Methide Derivativesen_US
dc.typePostprinten_US

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