Department of Chemistry, College of William and Mary, Williamsburg, Virginia 23185, USA.
J Phys Chem B. 2013 Mar 28;117(12):3323-7. doi: 10.1021/jp400765x. Epub 2013 Mar 20.
The local solvent acidities (SA scale) of six 6-carbonyl-2-aminonaphthalene derivatives as β-cyclodextrin complexes in water are determined through fluorescence quenching. The local polarities (E(T)(N) scale) are determined through the shift of the emission center-of-mass. The apparent SA values reflect the solvent structure surrounding the guest’s carbonyl group, whereas the apparent E(T)(N) values reveal the net polarity of the entire guest molecule. Comparison of these values affords greater insight into the structures of the host–guest complexes. Derivatives 1 and 5 show unusually large acidities, indicative of highly exposed carbonyl groups. The remaining compounds give emission intensities pointing to shielded carbonyl groups. In this study, PRODAN and its derivatives are functioning as dual channel sensors of their local environment.
通过荧光猝灭法测定了六种 6-羰基-2-氨基萘衍生物作为β-环糊精配合物在水中的局部溶剂酸度（SA 标度）。通过发射质心的移动来测定局部极性（E(T)(N)标度）。表观 SA 值反映了客体羰基基团周围的溶剂结构，而表观 E(T)(N)值揭示了整个客体分子的净极性。比较这些值可以更深入地了解主体-客体配合物的结构。衍生物 1 和 5 表现出异常大的酸度，表明羰基基团高度暴露。其余化合物的发射强度表明羰基基团受到屏蔽。在这项研究中，PRODAN 及其衍生物作为其局部环境的双通道传感器发挥作用。
