Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements

Mayu Fujii, Misa Namba, Minoru Yamaji, Hideki Okamoto

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A series of amino-2,3-naphthalimide derivatives having the amino functionality at 1-, 5- and 6-positions (1ANI, 5ANI and 6ANI, respectively) were prepared, and their photophysical properties were systematically investigated based on the measurements of steady-state absorption and fluorescence spectra, fluorescence lifetimes as well as transient absorption spectra. The ANIs efficiently fluoresced in solution, and the emission spectra appreciably shifted depending on the solvent polarity. 1ANI displayed only a slight fluorescence red-shift upon increasing the solvent polarity. In contrast, 5ANI and 6ANI showed marked positive solvatofluorochromism with large Stokes shifts displaying multicolour fluorescence; the fluorescence colours of 5ANI and 6ANI varied from violet-blue in hexane to orange-red in methanol. 5ANI and 6ANI, thus, serve as micro-environment responding fluorophores. In methanol, the intensity of the fluorescence emission band of 5ANI and 6ANI significantly reduced. Based on the fluorescence quantum yields and lifetimes, and transient absorption measurements, it has been revealed that internal conversion from the S1 state of ANIs to the ground state was accelerated by the protic medium, resulting in a reduction in their fluorescence efficiency, while intersystem crossing from the S1 state to a triplet state was not responsible for the decrease of fluorescence intensity.

Original languageEnglish
Pages (from-to)842-850
Number of pages9
JournalPhotochemical and Photobiological Sciences
Volume15
Issue number7
DOIs
Publication statusPublished - 2016

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Naphthalimides
Fluorescence
fluorescence
Methanol
polarity
methyl alcohol
absorption spectra
life (durability)
Fluorophores
internal conversion
Hexanes
Quantum yield
red shift
Ground state
atomic energy levels
Absorption spectra
emission spectra

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements. / Fujii, Mayu; Namba, Misa; Yamaji, Minoru; Okamoto, Hideki.

In: Photochemical and Photobiological Sciences, Vol. 15, No. 7, 2016, p. 842-850.

Research output: Contribution to journalArticle

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