当前位置: X-MOL 学术J. Org. Chem. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Building a Functionalizable, Potent Chemiluminescent Agent: A Rational Design Study on 6,8-Substituted Luminol Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-08-05 , DOI: 10.1021/acs.joc.1c00890
Theodoros Mikroulis 1 , M Consuelo Cuquerella 2 , Angelo Giussani 3 , Anna Pantelia 1 , Gemma M Rodríguez-Muñiz 2 , Georgios Rotas 1 , Daniel Roca-Sanjuán 3 , Miguel A Miranda 2 , Georgios C Vougioukalakis 1
Affiliation  

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.

中文翻译:

构建可功能化的有效化学发光剂:6,8-取代鲁米诺衍生物的合理设计研究

Luminol 是一种突出的化学发光 (CL) 试剂,在众多领域都有应用,包括法医学、免疫测定和成像。芳环上不同的取代模式可以提高或降低其 CL 效率。我们在此报告了对所有可能带有 H、Ph 和/或 Me 取代基的 6,8-二取代鲁米诺衍生物的合成和光物理学的系统研究。它们的 CL 响应在三个 pH 值(8、10 和 12)下进行监测,从而揭示了具有最佳 CL 效率的架构。最有效的模式用于合成强 CL 鲁米诺衍生物,带有用于进一步直接衍生化的官能团。该加合物在 pH = 12、pH = 10、与鲁米诺相比,尤其是在 pH = 8(更接近生物学相关条件)时。对发射物种的荧光以及量子化学计算的补充工作用于观察结果的合理化。
更新日期:2021-09-03
down
wechat
bug