Effect of protonation and hydrogen bonding on the fluorescent properties and exciplex formation of N-(4-pyridyl)-1,2-naphthalimide

Krisztina Sebok-Nagy, L. Biczók

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12 Citations (Scopus)

Abstract

The effects of fluorinated hydroxy compounds and naphthalene on the fluorescence of N-(4-pyridyl)-1,2-naphthalimide (PyNI) have been studied in toluene. The interaction of the pyridyl moiety of PyNI with hexafluoro-2-propanol (HFIP) gave rise to a hydrogen-bonded complex, whereas a more stable, hydrogen-bonded ion pair was formed with trifluoroacetic acid (TFA). Time-resolved fluorescence measurements demonstrate that hydrogen bonding with HFIP is a reversible process, even in the excited state, and revealed the rate constants of the various energy dissipation processes. The fluorescence yield enhancement of about one order of magnitude upon the 1 : 1 binding of PyNI to HFIP or TFA is primarily attributed to the deceleration of the internal conversion, and the fluorescence proved to be the dominant deactivation pathway of the singlet excited complexes. Both PyNI and its TFA complex produced fluorescent exciplexes with naphthalene. Protonation of PyNI markedly decreases the energy of the exciplex, leading to faster radiationless energy dissipation as well as to slow dissociation into an excited PyNI-TFA complex and ground-state naphthalene.

Original languageEnglish
Pages (from-to)389-395
Number of pages7
JournalPhotochemical and Photobiological Sciences
Volume3
Issue number4
DOIs
Publication statusPublished - Apr 2004

Fingerprint

Naphthalimides
Protonation
Hydrogen Bonding
Trifluoroacetic Acid
Hydrogen bonds
naphthalene
fluorescence
acids
hydrogen
Fluorescence
energy dissipation
Hydrogen
Energy dissipation
internal conversion
deceleration
deactivation
toluene
Deceleration
Toluene
dissociation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Cell Biology
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biophysics

Cite this

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title = "Effect of protonation and hydrogen bonding on the fluorescent properties and exciplex formation of N-(4-pyridyl)-1,2-naphthalimide",
abstract = "The effects of fluorinated hydroxy compounds and naphthalene on the fluorescence of N-(4-pyridyl)-1,2-naphthalimide (PyNI) have been studied in toluene. The interaction of the pyridyl moiety of PyNI with hexafluoro-2-propanol (HFIP) gave rise to a hydrogen-bonded complex, whereas a more stable, hydrogen-bonded ion pair was formed with trifluoroacetic acid (TFA). Time-resolved fluorescence measurements demonstrate that hydrogen bonding with HFIP is a reversible process, even in the excited state, and revealed the rate constants of the various energy dissipation processes. The fluorescence yield enhancement of about one order of magnitude upon the 1 : 1 binding of PyNI to HFIP or TFA is primarily attributed to the deceleration of the internal conversion, and the fluorescence proved to be the dominant deactivation pathway of the singlet excited complexes. Both PyNI and its TFA complex produced fluorescent exciplexes with naphthalene. Protonation of PyNI markedly decreases the energy of the exciplex, leading to faster radiationless energy dissipation as well as to slow dissociation into an excited PyNI-TFA complex and ground-state naphthalene.",
author = "Krisztina Sebok-Nagy and L. Bicz{\'o}k",
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N2 - The effects of fluorinated hydroxy compounds and naphthalene on the fluorescence of N-(4-pyridyl)-1,2-naphthalimide (PyNI) have been studied in toluene. The interaction of the pyridyl moiety of PyNI with hexafluoro-2-propanol (HFIP) gave rise to a hydrogen-bonded complex, whereas a more stable, hydrogen-bonded ion pair was formed with trifluoroacetic acid (TFA). Time-resolved fluorescence measurements demonstrate that hydrogen bonding with HFIP is a reversible process, even in the excited state, and revealed the rate constants of the various energy dissipation processes. The fluorescence yield enhancement of about one order of magnitude upon the 1 : 1 binding of PyNI to HFIP or TFA is primarily attributed to the deceleration of the internal conversion, and the fluorescence proved to be the dominant deactivation pathway of the singlet excited complexes. Both PyNI and its TFA complex produced fluorescent exciplexes with naphthalene. Protonation of PyNI markedly decreases the energy of the exciplex, leading to faster radiationless energy dissipation as well as to slow dissociation into an excited PyNI-TFA complex and ground-state naphthalene.

AB - The effects of fluorinated hydroxy compounds and naphthalene on the fluorescence of N-(4-pyridyl)-1,2-naphthalimide (PyNI) have been studied in toluene. The interaction of the pyridyl moiety of PyNI with hexafluoro-2-propanol (HFIP) gave rise to a hydrogen-bonded complex, whereas a more stable, hydrogen-bonded ion pair was formed with trifluoroacetic acid (TFA). Time-resolved fluorescence measurements demonstrate that hydrogen bonding with HFIP is a reversible process, even in the excited state, and revealed the rate constants of the various energy dissipation processes. The fluorescence yield enhancement of about one order of magnitude upon the 1 : 1 binding of PyNI to HFIP or TFA is primarily attributed to the deceleration of the internal conversion, and the fluorescence proved to be the dominant deactivation pathway of the singlet excited complexes. Both PyNI and its TFA complex produced fluorescent exciplexes with naphthalene. Protonation of PyNI markedly decreases the energy of the exciplex, leading to faster radiationless energy dissipation as well as to slow dissociation into an excited PyNI-TFA complex and ground-state naphthalene.

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