Effect of N-pyridyl substitution and hydrogen bonding on the deactivation of singlet excited 1,2-naphthalimide

Krisztina Nagy, L. Biczók

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Photophysical properties of 1,2-naphthalimide (1) and N-(4-pyridyl)-1,2-naphthalimide (2) as well as the effect of their hydrogen bonding with phenols have been studied in toluene. Fluorescence emission is the dominant energy dissipation pathway of the singlet excited 1. Introduction of the 4-pyridyl substituent into the imide moiety significantly accelerates the internal conversion due to the efficient vibronic coupling between close-lying S1 and S2 excited states, however, the rate of triplet formation exhibits negligible change. In contrast with the behavior of the corresponding substituted phenyl derivatives, 2 does not emit dual fluorescence because of the less extensive conjugation within the molecule. Fluorescence quenching with phenols takes place both in dynamic and static processes. Electron transfer is slower in the hydrogen bonded complex where phenols are linked to the pyridyl moiety due to the larger distance between the electron donor and acceptor components.

Original languageEnglish
Pages (from-to)837-846
Number of pages10
JournalResearch on Chemical Intermediates
Volume28
Issue number7-9
Publication statusPublished - 2002

Fingerprint

Naphthalimides
Phenols
Hydrogen bonds
Substitution reactions
Fluorescence
Imides
Electrons
Toluene
Excited states
Hydrogen
Quenching
Energy dissipation
Derivatives
Molecules

Keywords

  • Electron transfer
  • Fluorescence
  • Hydrogen bonding
  • Internal conversion

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Effect of N-pyridyl substitution and hydrogen bonding on the deactivation of singlet excited 1,2-naphthalimide. / Nagy, Krisztina; Biczók, L.

In: Research on Chemical Intermediates, Vol. 28, No. 7-9, 2002, p. 837-846.

Research output: Contribution to journalArticle

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