Journal
DYES AND PIGMENTS
Volume 99, Issue 2, Pages 456-464Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2013.05.033
Keywords
Asymmetric perylene bisimides; Intramolecular charge transfer; Solvatochromism; Solvatofluorism; Lippert-Mataga equation; 1-Cyano-7-piperidinylperylene bisimide
Funding
- National Science Council of the Republic of China [NSC 101-2113-M-035-001-MY2]
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Two asymmetric perylene bisimide dyes, 1-cyano-7-piperidinylperylene bisimide (1) and 1-bromo-7-piperidinylperylene bisimide (2), were synthesized and fully characterized. These molecules undergo an excited-state intramolecular electron transfer reaction, resulting in a unique charge transfer emission, of which the peak wavelength exhibits strong solvatochromism. They show both larger ground-state and excited-state dipole moments than those of the symmetric perylene bisimide 3; the dipole moments of these compounds have been estimated using density functional theory calculations and the Lippert-Mataga equation. Furthermore, these dyes (1-3) display good thermal stability as well as good optical stability and reversible redox properties. Their spectroscopic properties in various conditions and complementary time-dependent density functional theory calculations are reported. (C) 2013 Elsevier Ltd. All rights reserved.
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