Hydroxybenzo[b]quinolizinium Ions: Water-Soluble and Solvatochromic Photoacids

dc.contributor.authorSchäfer, Katy
dc.contributor.authorIhmels, Heiko
dc.contributor.authorBohne, Cornelia
dc.contributor.authorPapera Valente, Karolina
dc.contributor.authorGranzhan, Anton
dc.date.accessioned2017-07-18T16:21:38Z
dc.date.copyright2016en_US
dc.date.issued2016
dc.description.abstractIt is shown by photometric and fluorimetric analysis, along with supporting theoretical calculations, that hydroxy-substituted benzo[b]quinolizinium derivatives display the characteristic features of organic photoacids. Specifically, the experimental and theoretical results confirm the strong acidity of these compounds in the excited state (pKa* < 0). The combination of the prototropic properties of 8- and 9-hydroxybenzo[b]quinolizinium with the particular solvent–solute interactions of the excited acid and its conjugate base leads to a pronounced fluorosolvatochromism, hence the emission maxima shift from 468 nm (8-hydroxybenzo[b]quinolizinium) or 460 nm (9-hydroxybenzo[b]quinolizinium) in CH3CN to 507 and 553 nm in DMF, respectively. This novel type of photoacid represents several features that may be used for applications as water-soluble fluorescent probes or as a source for the photoinduced supply of acidity.en_US
dc.description.embargo2017-10-18
dc.description.reviewstatusRevieweden_US
dc.description.scholarlevelFacultyen_US
dc.description.sponsorshipThis work was generously financed by the Deutsche Forschungsgemeinschaft (IH24/10- 1). The authors at the University of Victoria thank the Natural Science and Engineering Research Council Canada for financial support (RGPIN-121389-2012).en_US
dc.identifier.citationSchafer, K. et al., (2016). Hydroxybenzo[b]quinolizinium Ions: Water-Soluble and Solvatochromic Photoacids. The Journal of Organic Chemistry, 81, 10942-10954. doi: 10.1021/acs.joc.6b0199en_US
dc.identifier.urihttp://dx.doi.org/10.1021/acs.joc.6b01991
dc.identifier.urihttp://hdl.handle.net/1828/8352
dc.language.isoenen_US
dc.publisherThe Journal of Organic Chemistryen_US
dc.titleHydroxybenzo[b]quinolizinium Ions: Water-Soluble and Solvatochromic Photoacidsen_US
dc.typeArticleen_US

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