Comparison of the absorption, emission, and resonance Raman spectra of 7-hydroxyquinoline and 8-bromo-7-hydroxyquinoline caged acetate

Jiani Ma, Shun Cheung Cheng, Huiying An, Ming De Li, Chensheng Ma, Adam C. Rea, Yue Zhu, Jameil L. Nganga, Timothy M. Dore, David Lee Phillips

Research output: Contribution to journalArticlepeer-review

Abstract

To better understand the deprotection reaction of the new promising phototrigger compound BHQ-OAc (8-bromo-7-hydroxyquinoline acetate), we present a detailed comparison of the UV-vis absorption, resonance Raman, and fluorescence spectra of BHQ-OAc with its parent compound 7-hydroxyquinoline in different solvents. The steady-state absorption and resonance Raman spectra provide fundamental information about the structure, properties, and population distribution of the different prototropic forms present under the different solvent conditions examined. The species present in the excited states that emit strongly were detected by fluorescence spectra. It is shown that the ground-state tautomerization process of BHQ-OAc is disfavored compared with that of 7-HQ in aqueous solutions. The observation of the tautomeric form of BHQ-OAc in neutral aqueous solutions demonstrates the occurrence of the excited-state proton-transfer process, which would be a competing process for the deprotection reaction of BHQ-OAc in aqueous solutions.

Original languageEnglish (US)
Pages (from-to)11632-11640
Number of pages9
JournalJournal of Physical Chemistry A
Volume115
Issue number42
DOIs
StatePublished - Oct 27 2011

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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