Citation: Tzu-Chien Fang, Hsing-Yang Tsai, Ming-Hui Luo, Che-Wei Chang, Kew-Yu Chen. Excited-state charge coupled proton transfer reaction via the dipolar functionality of salicylideneaniline[J]. Chinese Chemical Letters, ;2013, 24(2): 145-148. shu

Excited-state charge coupled proton transfer reaction via the dipolar functionality of salicylideneaniline

1.
Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan

Corresponding author: Kew-Yu Chen,
Received Date: 27 September 2012
Available Online: 14 December 2012
Fund Project: We thank the National Science Council (No. NSC 101-2113-M-035-001-MY2) for the financial support. (No. NSC 101-2113-M-035-001-MY2)

Based on design and synthesis of salicylideneaniline derivatives (1a-1d), we demonstrate a prototypical system to investigate the excited-state intramolecular charge transfer (ESICT) coupled excited-state intramolecular proton transfer (ESIPT) reaction via the dipolar functionality of the molecular framework. In solid and aprotic solvents 1a-1d exist mainly as E conformers that possess an intramolecular sixmembered-ring hydrogen bond. Compounds 1a-1c exhibit a unique proton-transfer tautomer emission, while compound 1d exhibits remarkable dual emission due to the different solvent-polarity environment between ESICT and ESIPT states. Time-dependent density functional theory (TDDFT) calculations are reported on these Schiff bases in order to rationalize their electronic structure and absorption spectra.
- ESIPT,
- ESICT,
- Dipolar functionality,
- Salicylideneaniline derivatives
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