TY - JOUR
T1 - Synthesis and photochemical behavior of donor-acceptor systems obtained from chloro-1,4-naphthoquinone attached to trans-aminostilbenes
AU - Sutovsky, Y.
AU - Likhtenshtein, G. I.
AU - Bittner, S.
N1 - Funding Information:
This research was supported by the Israel Science Foundation founded by the Academy of Science and Humanities and German-Israel James Frank Program on Laser-Matter Interaction. We wish to thank Ms Ethel Solomon for skilled technical help and A. Novoselsky for his advice on NMR spectroscopy. We greatly appreciate Dr S. Kolusheva for obtaining the fluorescence lifetime data and helpful discussions.
PY - 2003/4/14
Y1 - 2003/4/14
N2 - 2-Chloro-1,4-naphthoquinone was covalently attached to six differently substituted and positional isomers of trans-aminostilbene, forming a novel donor-acceptor system (QST), in which a good fluorophore is bonded via an NH group to an active redox quencher. The new systems were characterized by FT-IR, 1H NMR, HR-MS, UV-Vis and fluorescence spectroscopy. The redox state of the system QST/QH2ST controls its photochemical properties. While the QST's behave as an 'auto-quenching system' and are non-fluorescent, the reduced hydroquinonic system (QH2ST) affects appreciably the emission properties of the molecule.
AB - 2-Chloro-1,4-naphthoquinone was covalently attached to six differently substituted and positional isomers of trans-aminostilbene, forming a novel donor-acceptor system (QST), in which a good fluorophore is bonded via an NH group to an active redox quencher. The new systems were characterized by FT-IR, 1H NMR, HR-MS, UV-Vis and fluorescence spectroscopy. The redox state of the system QST/QH2ST controls its photochemical properties. While the QST's behave as an 'auto-quenching system' and are non-fluorescent, the reduced hydroquinonic system (QH2ST) affects appreciably the emission properties of the molecule.
KW - Aminostilbene
KW - Fluorescence quenching
KW - Hydroquinone
KW - Molecular switching system
KW - Quinone
UR - http://www.scopus.com/inward/record.url?scp=0037437113&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(03)00213-8
DO - 10.1016/S0040-4020(03)00213-8
M3 - Article
AN - SCOPUS:0037437113
SN - 0040-4020
VL - 59
SP - 2939
EP - 2945
JO - Tetrahedron
JF - Tetrahedron
IS - 16
ER -