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Kinetic analysis of tautomer forms of aromatic-urea compounds with acetate ions: solvent effect of excited state intermolecular proton transfer†
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2018-03-19 00:00:00 , DOI: 10.1039/c8pp00018b
Hisato Matsumoto 1, 2, 3, 4 , Satomi Ikedu 1, 2, 3, 4 , Takeyuki Tosaka 1, 2, 3, 4 , Yoshinobu Nishimura 1, 2, 3, 4 , Tatsuo Arai 1, 2, 3, 4
Affiliation  

In this paper, we report the solvent effect of excited state intermolecular proton transfer (ESIPT) reactions of urea compounds in the presence of tetrabutylammonium acetate (TBAAc). We prepared anthracene-urea compounds (9An and 2An), a pyrene-urea compound (Py) and an anthracene-diurea compound (9,10An), which have alkylsulfonyl groups to improve their solubility in various organic solvents. We investigated the solvent effects of the ESIPT reaction using absorption, fluorescence, and 1H NMR spectroscopy along with fluorescence decay measurements in dimethyl sulfoxide (DMSO), acetonitrile (MeCN), tetrahydrofuran (THF) and toluene. The tautomer fluorescence of 9An showed remarkable solvent dependence on the spectral red-shift compared with 2An, Py and 9,10An. As a result of the detailed spectroscopic investigations with regard to the solvent including kinetic analysis of the ESIPT for 9An⋯AcO, we revealed that the energy gap between the normal and tautomer forms in the excited state depended on the hydrogen bond acceptor basicity (β), which is one of the Kamlet–Taft solvent parameters. Finally, we discovered that the tautomer structures of aromatic-urea compounds were stabilized by hydrogen bond interactions.

中文翻译:

含乙酸根离子的芳香族脲化合物互变异构体形式的动力学分析:激发态分子间质子转移的溶剂效应

在本文中,我们报告了在乙酸四丁铵(TBAAc)存在下脲化合物的激发态分子间质子转移(ESIPT)反应的溶剂效应。我们制备了具有烷基磺酰基的蒽-脲化合物(9An2An),a-脲化合物(Py)和蒽-二脲化合物(9,10An),以提高它们在各种有机溶剂中的溶解度。我们使用吸收,荧光和1 H NMR光谱研究了ESIPT反应的溶剂效应,并在二甲基亚砜(DMSO),乙腈(MeCN),四氢呋喃(THF)和甲苯中进行了荧光衰减测量。9An的互变异构体荧光2AnPy9,10An相比,对光谱红移显示出显着的溶剂依赖性。如关于包括ESIPT用于动力学分析的溶剂的详细光谱研究的结果9AN ⋯ACO - ,我们发现,在激发态的正常和互变异构体形式之间的能隙依赖于氢键受体碱度(β),这是Kamlet-Taft溶剂参数之一。最后,我们发现芳香族脲化合物的互变异构体结构通过氢键相互作用得以稳定。
更新日期:2018-03-19
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