Agafontsev Aleksandr M, Shumilova Tatiana A, Panchenko Pavel A, Janz Sharon, Fedorova Olga A, Kataev Evgeny A
Institute of Chemistry, Technische Universität Chemnitz, 09107, Chemnitz, Germany), Fax: +49 (0) 371 531 839841.
Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia.
Chemistry. 2016 Oct 10;22(42):15069-15074. doi: 10.1002/chem.201602623. Epub 2016 Sep 5.
A receptor containing amidopyrrole binding subunits and free amino groups, conjugated to a naphthalimide dye, has been designed and synthesized. The intrinsic selectivity of the binding motif for phosphate present in DMSO completely disappears in 10 % DMSO aqueous buffer at pH 3.6, at which the receptor is protonated. The electrostatic interactions between the receptor and an anion start to dominate, thus leading to selectivity for sulfate. The ability of the HSO anion to transfer the proton to the amino group during the recognition event suppresses the photoinduced electron transfer (PET) on the dye, resulting in a selective turn-on fluorescent response. The choice of pH of the solution for sensing is dictated by the pK value of the dye.
一种含有氨基吡咯结合亚基和游离氨基的受体,与萘二甲酰亚胺染料共轭,已被设计并合成。在pH为3.6的10%二甲基亚砜水溶液缓冲液中,受体质子化,此时二甲基亚砜中存在的磷酸盐结合基序的固有选择性完全消失。受体与阴离子之间的静电相互作用开始起主导作用,从而导致对硫酸盐的选择性。在识别过程中,硫酸氢根阴离子将质子转移到氨基的能力抑制了染料上的光致电子转移(PET),从而产生选择性的开启荧光响应。用于传感的溶液pH值的选择由染料的pK值决定。