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Polyimide and Imide Compound Exhibiting Bright Red Fluorescence with Very Large Stokes Shifts via Excited-State Intramolecular Proton Transfer II. Ultrafast Proton Transfer Dynamics in the Excited State

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Department of Chemistry and Materials Science, Tokyo Institute of Technology, Ookayama 2-12-1-E4-5, Meguro-ku, Tokyo 152-8552, Japan
Center for Physical Sciences and Technology, Savanorių Ave. 231, Vilnius LT-02300, Lithuania
§ Institute of Materials Science, Kaunas University of Technology, K. Baršausko g. 59, Kaunas LT-51423, Lithuania
*E-mail [email protected] (S.A.).
*E-mail [email protected] (V.G.).
Cite this: Macromolecules 2016, 49, 5, 1848–1857
Publication Date (Web):February 22, 2016
https://doi.org/10.1021/acs.macromol.5b02224
Copyright © 2016 American Chemical Society

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    Abstract

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    A novel polyimide (PI) and imide compound emitting prominent reddish-orange fluorescence under excitation by UV light were prepared based on 3-hydroxypyromellitic dianhydride (PHDA), and their fluorescence properties were examined. The steady-state fluorescence spectrum of a PI film displayed an emission band at 590 nm with a very large Stokes shift (ν = 10 448 cm–1) via the excited-state intramolecular proton transfer (ESIPT), while the time-resolved fluorescence spectrum showed a rapid decay of the emission band of the enol form at around 400 nm within 15 ps. Transient absorption measurements showed an induced absorption and stimulated emission of the keto form with a time constant of ca. 3.0 ps, implying that ESIPT occurs on this time scale. Consequently, introduction of a hydroxy group into the pyromellitic moiety of PIs and imide compounds led to the long-wavelength ESIPT emission applicable to spectral converters having high thermal, mechanical, and environmental stabilities.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.macromol.5b02224.

    • Synthesis part and figures showing the calculated MOs of the enol and keto forms of 3H-MC (TD-DFT method at the ωB97X-D/6-311++G(d,p) level), the concentration-dependent absorption spectra of 3H-MC in CHCl3, TGA curve of the 3H-PI film, the steady-state emission spectra of the 3H-PI film at lower temperatures, and the transient absorption spectra of the 3H-PI film when the pump pulse wavelength was 455 nm (PDF)

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