羰基扭曲的 6-酰基-2-二烷基氨基萘作为溶剂酸度传感器。
Carbonyl-twisted 6-acyl-2-dialkylaminonaphthalenes as solvent acidity sensors.
机构信息
Department of Chemistry, College of William and Mary, Williamsburg, Virginia 23187-8795, United States.
出版信息
J Org Chem. 2013 Mar 1;78(5):1784-9. doi: 10.1021/jo301263g. Epub 2012 Aug 21.
Abstract
Derivatives of 2-propionyl-6-dimethylaminonaphthalene (PRODAN) with twisted carbonyl groups were investigated as highly responsive sensors of H-bond donating ability. The PRODAN derivative bearing a pivaloyl group (4) was prepared. The torsion angle between the carbonyl and naphthalene is 26° in the crystal. It shows solvatochromism that is similar to five other PRODAN derivatives (1-3, 5, 6). Twisted-carbonyl derivatives 3, 4, and 6 show strong fluorescence quenching in protic solvents. The order of magnitude of the quenching is linearly related to the H-bond donating ability of the solvent (SA) but not to other solvent properties. Binary mixtures of protic solvents show specific interaction effects with respect to quenching and solvatochromism. Aggregation in water is an issue with the pivaloyl derivatives.
摘要
研究了具有扭曲羰基的 2-丙酰基-6-二甲基氨基萘（PRODAN）衍生物作为对氢键供体能力高度敏感的传感器。制备了带有特戊酰基的 PRODAN 衍生物（4）。在晶体中，羰基和萘之间的扭转角为 26°。它表现出类似于其他五个 PRODAN 衍生物（1-3、5、6）的溶剂致变色。扭曲羰基衍生物 3、4 和 6 在质子溶剂中显示出强烈的荧光猝灭。猝灭的数量级与溶剂的氢键供体能力（SA）呈线性相关，但与其他溶剂性质无关。质子溶剂的二元混合物在猝灭和溶剂致变色方面表现出特定的相互作用效应。特戊酰衍生物在水中存在聚集问题。
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本文引用的文献
1
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J Fluoresc. 1991 Dec;1(4):215-23. doi: 10.1007/BF00865246.
2
Polarity-sensitive fluorescent probes in lipid bilayers: bridging spectroscopic behavior and microenvironment properties.脂质双层中对极性敏感的荧光探针：连接光谱行为和微环境特性。
J Phys Chem B. 2011 Aug 25;115(33):9980-9. doi: 10.1021/jp205163w. Epub 2011 Aug 4.
3
What is solvatochromism?什么是溶剂变色现象？
J Phys Chem B. 2010 Dec 30;114(51):17128-35. doi: 10.1021/jp1097487. Epub 2010 Dec 3.
4
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J Phys Chem A. 2010 Apr 15;114(14):4946-50. doi: 10.1021/jp1002808.
5
Solvation dynamics of the fluorescent probe PRODAN in heterogeneous environments: contributions from the locally excited and charge-transferred states.荧光探针PRODAN在非均相环境中的溶剂化动力学：来自局域激发态和电荷转移态的贡献。
J Phys Chem B. 2009 Sep 3;113(35):11999-2004. doi: 10.1021/jp905139n.
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Toward a generalized treatment of the solvent effect based on four empirical scales: dipolarity (SdP, a new scale), polarizability (SP), acidity (SA), and basicity (SB) of the medium.基于四个经验标度：介质的偶极性（SdP，一个新标度）、极化率（SP）、酸度（SA）和碱度（SB），对溶剂效应进行广义处理。
J Phys Chem B. 2009 Apr 30;113(17):5951-60. doi: 10.1021/jp8095727.
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