TY - JOUR
T1 - Hydroquinone-benzonitrile system
T2 - Intramolecular charge-transfer and computational studies
AU - Sung, Kuangsen
AU - Huang, Pin Mei
AU - Zhou, Chi Han
N1 - Funding Information:
Acknowledgments Financial support from the National Science Council of Taiwan (NSC 95-2113-M-006-008) is gratefully acknowledged. We thank National Center for High-Performance Computing of Taiwan for computer time.
PY - 2007/9
Y1 - 2007/9
N2 - A novel intramolecular donor-acceptor system of hydroquinone-benzonitrile was synthesized. Its photo-induced intramolecular charge-transfer (ICT) transition was confirmed by (1) shift of its emission maximum with increasing solvent polarity, (2) high dipole moment for the ICT excited state calculated from the Lippert equation, and (3) its HOMO and LUMO. According to the extent of separation between HOMO and LUMO, it is suggested that substituent position (ortho, meta, or para) in the donor-acceptor biphenyls is not a key point for the photo-induced intramolecular charge transfer and the donor with two alkoxy or hydroxy groups has more photo-induced charge transfer transitions than the one with one alkoxy or hydroxy group. In other words, the hydroquinone- benzonitrile system displays more photo-induced charge transfer transitions than 4COB (4-cyano-4'-butyloxybiphenyl).
AB - A novel intramolecular donor-acceptor system of hydroquinone-benzonitrile was synthesized. Its photo-induced intramolecular charge-transfer (ICT) transition was confirmed by (1) shift of its emission maximum with increasing solvent polarity, (2) high dipole moment for the ICT excited state calculated from the Lippert equation, and (3) its HOMO and LUMO. According to the extent of separation between HOMO and LUMO, it is suggested that substituent position (ortho, meta, or para) in the donor-acceptor biphenyls is not a key point for the photo-induced intramolecular charge transfer and the donor with two alkoxy or hydroxy groups has more photo-induced charge transfer transitions than the one with one alkoxy or hydroxy group. In other words, the hydroquinone- benzonitrile system displays more photo-induced charge transfer transitions than 4COB (4-cyano-4'-butyloxybiphenyl).
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U2 - 10.1007/s10895-007-0199-8
DO - 10.1007/s10895-007-0199-8
M3 - Article
C2 - 17629718
AN - SCOPUS:34548163397
SN - 1053-0509
VL - 17
SP - 492
EP - 499
JO - Journal of Fluorescence
JF - Journal of Fluorescence
IS - 5
ER -