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Building a functionalizable, potent chemiluminescent agent: A rational design study on 6,8-substituted luminol derivatives

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Building a functionalizable, potent chemiluminescent agent: A rational design study on 6,8-substituted luminol derivatives
Theodoros Mikroulis, M. Consuelo Cuquerella, Angelo Giussani, Anna Pantelia, Gemma M. Rodríguez- Muñiz, Georgios Rotas, Daniel Roca-Sanjuán, Miguel A. Miranda, and Georgios C. Vougioukalakis
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. (EN)
preprint
Εργασία εν εξελίξει (Preprint) (EL)
Preprint (EN)
Θετικές Επιστήμες (EL)
Science (EN)
University of Athens
Pergamos Digital Library
Preprint
English
2021-01-01
uoadl:2959448
https://pergamos.lib.uoa.gr/uoa/dl/object/uoadl:2959448



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