title: Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements.
abstract: A series of amino-2,3-naphthalimide derivatives having the amino functionality at 1-, 5- and 6-positions (, and , 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 s efficiently fluoresced in solution, and the emission spectra appreciably shifted depending on the solvent polarity. displayed only a slight fluorescence red-shift upon increasing the solvent polarity. In contrast, and showed marked positive solvatofluorochromism with large Stokes shifts displaying multicolour fluorescence; the fluorescence colours of and varied from violet-blue in hexane to orange-red in methanol. and , thus, serve as micro-environment responding fluorophores. In methanol, the intensity of the fluorescence emission band of and 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 s 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.
authors.affiliation: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University, Okayama 700-8350, Japan. hokamoto@okayama-u.ac.jp.
authors.forename: Mayu
authors.initials: M
authors.lastname: Fujii
authors.affiliation: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University, Okayama 700-8350, Japan. hokamoto@okayama-u.ac.jp.
authors.forename: Misa
authors.initials: M
authors.lastname: Namba
authors.affiliation: Division of Molecular Science, Graduate School of Science and Engineering, Gunma University, Kiryu, Gunma 376-8515, Japan.
authors.forename: Minoru
authors.initials: M
authors.lastname: Yamaji
authors.affiliation: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University, Okayama 700-8350, Japan. hokamoto@okayama-u.ac.jp.
authors.forename: Hideki
authors.initials: H
authors.lastname: Okamoto
mesh_terms: D000432:Methanol / Q000737:chemistry; D053644:Naphthalimides / Q000737:chemistry*; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D053644:Naphthalimides; D012997:Solvents; D000432:Methanol