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

Simple item page
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

Files

Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
Schafer_Katy_JOC_2016.pdf
Size:
3.22 MB
Format:
Adobe Portable Document Format
Description:
Download
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.74 KB
Format:
Item-specific license agreed upon to submission
Description:
Download

Collections

Faculty Publications (BioMed Central & Faculty of Science)
 
University of Victoria Libraries

We acknowledge and respect the Lək̓ʷəŋən (Songhees and Esquimalt) Peoples on whose territory the university stands, and the Lək̓ʷəŋən and W̱SÁNEĆ Peoples whose historical relationships with the land continue to this day.