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

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Department of Chemistry
Building a functionalizable, potent chemiluminescent agent: A rational design study on 6,8-substituted luminol derivatives
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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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Theodoros Mikroulis, M. Consuelo Cuquerella, Angelo Giussani, Anna Pantelia, Gemma M. Rodríguez-
Muñiz, Georgios Rotas, Daniel Roca-Sanjuán, Miguel A. Miranda, and Georgios C.
Chemiluminescence, Luminescence, Luminol, Quantum chemistry computations, Imaging Agents
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This project was financially supported by the European Union’s Horizon 2020 framework program for research and innovation under grant agreement no. 712921. T.M. and A.P. would like to thank the State Scholarships Foundation (IKY) for financial support through PhD fellowships through the “Strengthening of Human Resources through Doctoral Research” program of the Operational Program “Human Resource Development, Education and Lifelong Learning” 2014-2020, co-financed by the Eu-ropean Union (European Social Fund ESF) and Greek national funds. M.A.M. and G.M.R.-M. thank the Generalitat Valenciana (Prometeo Pro-gram/2017/075) for financial support. A.G. and D.R.-S. acknowledge Spanish “Ministerio de Ciencia e Innovación (MICINN)” (Project Ref. CTQ2017-87054-C2-2-P). A. G. is also thankful to the MICINN for a “Juan de la Cierva” grant (Ref. IJC2018-035123-I). D.R.-S. is also thankful to the MICINN for a “Ramón y Cajal” grant (Ref. RYC-2015-19234) and to the BBVA Foundation for a 2019 Leonardo Grant for Researchers and Cultural Creators.
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