鲁米诺
化学
化学发光
衍生化
加合物
组合化学
荧光
光化学
有机化学
高效液相色谱法
量子力学
物理
作者
Theodoros Mikroulis,M. Consuelo Cuquerella,Angelo Giussani,Άννα Παντελιά,Gemma M. Rodríguez‐Muñiz,Georgios Rotas,Daniel Roca‐Sanjuán,Miguel A. Miranda,Georgios C. Vougioukalakis
标识
DOI:10.1021/acs.joc.1c00890
摘要
Luminol is a prominent chemiluminescent (CL) agent, finding applications across numerous fields, including forensics, immunoassays, and imaging. Different substitution patterns on the aromatic ring can enhance or decrease its CL efficiency. We herein report a systematic study on the synthesis and photophysics of all possible 6,8-disubstituted luminol derivatives bearing H, Ph, and/or Me substituents. Their CL responses are monitored at three pH values (8, 10, and 12), thus revealing the architecture with the optimum CL efficiency. The most efficient pattern is used for the synthesis of a strongly CL luminol derivative, bearing a functional group for further, straightforward derivatization. This adduct exhibits an unprecedented increase in chemiluminescence efficiency at pH = 12, pH = 10, and especially at pH = 8 (closer to the biologically relevant conditions) compared to luminol. Complementary work on the fluorescence of the emissive species as well as quantum chemistry computations are employed for the rationalization of the observed results.
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