Jump to main content
Jump to site search

Issue 32, 2015
Previous Article Next Article

Complexes of a naphthalimide photoacid with organic bases, and their excited-state dynamics in polar aprotic organic solvents

Author affiliations

Abstract

Complex formation and intermolecular excited-state proton transfer (ESPT) between a dihydroxy-1,8-naphthalimide photoacid and organic bases are investigated in polar aprotic solvents. First, quantum chemical calculations are used to explore the acid–base and spectroscopic properties and to identify energetically favorable complexes. The two hydroxyl groups of the photoacid enable stepwise formation of 1 : 1 and 1 : 2 complexes. Weak bases exhibit only hydrogen-bonding interactions whereas strong bases are able to deprotonate one of the hydroxyl groups resulting in strong negative cooperativity (K1 ≫ 4K2) in the formation of the 1 : 2 complex. Time-resolved fluorescence studies of the complexes provide strong indications of a three-step dissociation process. The species involved in the model are: a hydrogen-bonded complex, a hydrogen-bonded ion pair, a solvent separated ion pair, and a free ion pair.

Graphical abstract: Complexes of a naphthalimide photoacid with organic bases, and their excited-state dynamics in polar aprotic organic solvents

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 May 2015, accepted on 15 Jul 2015 and first published on 17 Jul 2015


Article type: Paper
DOI: 10.1039/C5CP02556G
Author version
available:
Download author version (PDF)
Citation: Phys. Chem. Chem. Phys., 2015,17, 20715-20724
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Complexes of a naphthalimide photoacid with organic bases, and their excited-state dynamics in polar aprotic organic solvents

    T. Kumpulainen, B. H. Bakker and A. M. Brouwer, Phys. Chem. Chem. Phys., 2015, 17, 20715
    DOI: 10.1039/C5CP02556G

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements