Lane Jakob D E, Jolliffe Katrina A
School of Chemistry, The University of Sydney, NSW, 2006, Australia.
Australian Research Council Centre of Excellence for Innovations in Peptide and Protein Science, The University of Sydney, 2006, NSW, Australia.
Org Biomol Chem. 2023 Apr 12;21(15):3226-3234. doi: 10.1039/d3ob00069a.
A series of fluorophore-containing squaramides were synthesised to investigate the fluorescent and colorimetric response to anions of squaramides containing large aromatic substituents. Squaramides in which the fluorophores were conjugated directed to the squaramide motif were found to have highly acidic NH protons, giving rise to complicated fluorescence behaviour and colour changes upon addition of anions. In contrast, squaramides incorporating a methylene spacer to electronically insulate the fluorophore from the squaramide gave a relatively simple fluorescence response upon addition of anions, which was attributed to a decrease in excimer emission relative to monomer emission intensity, likely due to a disaggregation mechanism. The ratio of excimer : monomer emission was used to provide a ratiometric fluorescent response to anions, with the most selective molecules demonstrating a preference for binding to sulfate over other anions.
合成了一系列含荧光团的方酰胺，以研究含大芳香取代基的方酰胺对阴离子的荧光和比色响应。发现荧光团与方酰胺基序共轭的方酰胺具有高酸性的NH质子，在加入阴离子后会产生复杂的荧光行为和颜色变化。相比之下，引入亚甲基间隔基以使荧光团与方酰胺在电子上绝缘的方酰胺在加入阴离子后给出相对简单的荧光响应，这归因于相对于单体发射强度，准分子发射的减少，这可能是由于解聚机制。准分子：单体发射的比率用于提供对方阴离子的比率荧光响应，最具选择性的分子表现出比对其他阴离子更倾向于与硫酸根结合。
