Enhanced fluorescence of phthalimide compounds induced by the incorporation of electron-donating alicyclic amino groups

Physical Chemistry Chemical Physics : PCCP
Ryoji OritaShinji Ando

Abstract

Due to their high thermal and environmental stability, polyimides (PIs) are one of the most attractive candidates for novel highly fluorescent polymers, though photophysical studies of PIs are challenging owing to their poor solubility in common solvents. To overcome these problems, we have synthesized and examined a series of low molecular weight model imide compounds: substituted N-cyclohexylphthalimides with alicyclic amino groups at the 3 or 4-positions of the benzene rings (x-NHPIs). Their photophysical properties were systematically investigated by steady-state UV/Visible absorption, fluorescence, and time-resolved fluorescence techniques. In solution, unsubstituted N-cyclohexylphthalimide (NHPI) showed almost no emission, while x-NHPIs exhibited enhanced fluorescence emission depending on the solvent polarity. Analysis of the solvatochromism of the x-NHPIs via Lippert-Mataga plots indicated the generation of large dipole moments in the excited singlet states originating from the intramolecular charge-transfer (ICT) states. The significant difference in the fluorescence quantum yields (Φ) between the 3-substituted (3Pi and 3Pyr) and 4-substituted NHPIs (4Pi and 4Pyr) strongly suggests that the former form a twisted ICT (T...Continue Reading

References

Feb 12, 2004·Journal of the American Chemical Society·Klaas A ZachariasseReinhard Machinek
Jul 9, 2004·Journal of the American Chemical Society·Toshitada YoshiharaKlaas A Zachariasse
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Oct 28, 2009·The Journal of Physical Chemistry. B·Junji WakitaShinji Ando
Feb 6, 2010·European Journal of Medicinal Chemistry·Wei WangJun-Biao Chang
Oct 18, 2012·Chemical Society Reviews·Xiaoyong HuangXiaogang Liu
Nov 3, 2015·Physical Chemistry Chemical Physics : PCCP·Kenta Kanosue, Shinji Ando
Jun 3, 2016·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Mayu FujiiHideki Okamoto
Apr 8, 2014·Science and Technology of Advanced Materials·Yutaka WakayamaHoon-Seok Seo

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Citations

Aug 16, 2018·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Lei WangHideki Okamoto

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Methods Mentioned

BETA
X-ray
NMR
Fluorescence
XRD

Software Mentioned

SHELXL
Gaussian
PICT
CAM

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