Journal
DYES AND PIGMENTS
Volume 91, Issue 3, Pages 269-278Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2011.05.004
Keywords
Diketo-pyrrolo-pyrrole; Fluorescence; Solvatochromism; Solid-state fluorescence; Twisted intramolecular charge transfer; Organic electronics
Funding
- Academy of Sciences of the Czech Republic [KAN401770651]
- Ministry of Industry and Trade of the Czech Republic [2A-1TP1/041]
- Czech Science Foundation [P205/10/2280]
- ERDF [CZ.1.05/2.1.00/01.0012]
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Six soluble derivatives of 3,6-diphenyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione N-alkylated on pyrrolinone ring with polar substituents in para positions of pendant phenyl rings were synthesized: five of them are reported for the first time. Absorption and fluorescence spectra were studied in solvents of different polarity. The compounds show small solvatochromism of absorption and a moderate positive solvatochromism of fluorescence, especially when substituted by strong electron-donating piperidino substituent. A significant decrease of fluorescence quantum yields and its biexponential decay for dipolar derivatives in polar solvents was tentatively ascribed to the formation of twisted intramolecular charge transfer (TICT) excited state. All six compounds show fluorescence in polycrystalline solid-state with the maxima covering a range over 200 nm in visible and near infrared region. (C) 2011 Elsevier Ltd. All rights reserved.
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