Journal
DYES AND PIGMENTS
Volume 104, Issue -, Pages 97-101Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2013.12.031
Keywords
1,4-Diketo-pyrrolo[3,4-c]pyrrole derivative; Suzuki coupling reaction; Fluorescence chemosensor; Fluoride anion; Two-photon absorption; Two-photon excitation fluorescence
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A fully aromatic D-pi-A-pi D-type molecule 3,6-bis[4-(4-(diphenylamino)-phenyl)phenyl]-N-octyl-1,4-diketo-pyrrolo13,4-c]pyrrole (TDP) was synthesized, and the one- and two-photon absorption and emission properties in the absence or presence of fluoride anion were investigated. The results show that TDP not only exhibits large two-photon absorption (2PA) cross section (delta) up to 1030 GM and strong red two-photon excitation fluorescence, but also could operate as one- and two-photon chemosensor selectively for fluoride anion. Interestingly, it is observed that both the detection sensitivity of TDP to fluoride anion and the ratiometric change in emission spectra upon two-photon induced by fluoride anion are higher than one-photon excitation, implying that TDP could serve better as two-photon fluorescence sensor for fluoride anion. The large delta and red-shifted 2PA band promoted by triphenyl-amine end-group enable TDP to sense fluoride anion under longer excitation wavelength and lower input laser power. (C) 2014 Elsevier Ltd. All rights reserved.
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