TY - JOUR
T1 - A diethylaminophenol functionalized Schiff base
T2 - crystallization-induced emission-enhancement, switchable fluorescence and application for security printing and data storage
AU - Han, Tianyu
AU - Feng, Xiao
AU - Chen, Didi
AU - Dong, Yuping
N1 - Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2015/7/28
Y1 - 2015/7/28
N2 - In this study, we report the synthesis and photoluminescence (PL) behaviour of a new luminogen, SBOH, a diethylaminophenol functionalized Schiff base. SBOH possesses electron donor (D) and acceptor (A) units, showing twisted intramolecular charge transfer (TICT) properties. Interestingly, SBOH is weakly emissive in the amorphous phase but becomes highly emissive upon crystallization as confirmed by spectroscopic methods and fluorescence microscopy; in other words, SBOH is crystallization-induced emission-enhancement (CIEE)-active. Similar to the typical CIEE luminogens, the emission of SBOH is also sensitive to molecular packing modes. The weak emission of amorphous SBOH can be switched on via a deprotonation process caused by strong alkali. Meanwhile, exposure to acetic acid vapour rapidly switches the emission to the "off" state through re-protonation. The protonation and deprotonation processes display good reversibility. This deprotonation process is further confirmed by 1H NMR analysis and UV-vis spectroscopy. By taking advantage of the stimuli responsive fluorescence, a convenient and efficient technology for security printing and data storage is designed.
AB - In this study, we report the synthesis and photoluminescence (PL) behaviour of a new luminogen, SBOH, a diethylaminophenol functionalized Schiff base. SBOH possesses electron donor (D) and acceptor (A) units, showing twisted intramolecular charge transfer (TICT) properties. Interestingly, SBOH is weakly emissive in the amorphous phase but becomes highly emissive upon crystallization as confirmed by spectroscopic methods and fluorescence microscopy; in other words, SBOH is crystallization-induced emission-enhancement (CIEE)-active. Similar to the typical CIEE luminogens, the emission of SBOH is also sensitive to molecular packing modes. The weak emission of amorphous SBOH can be switched on via a deprotonation process caused by strong alkali. Meanwhile, exposure to acetic acid vapour rapidly switches the emission to the "off" state through re-protonation. The protonation and deprotonation processes display good reversibility. This deprotonation process is further confirmed by 1H NMR analysis and UV-vis spectroscopy. By taking advantage of the stimuli responsive fluorescence, a convenient and efficient technology for security printing and data storage is designed.
UR - http://www.scopus.com/inward/record.url?scp=84938149104&partnerID=8YFLogxK
U2 - 10.1039/c5tc00891c
DO - 10.1039/c5tc00891c
M3 - Article
AN - SCOPUS:84938149104
SN - 2050-7526
VL - 3
SP - 7446
EP - 7454
JO - Journal of Materials Chemistry C
JF - Journal of Materials Chemistry C
IS - 28
ER -
