TY - JOUR
TI - Building a Functionalizable, Potent Chemiluminescent Agent: A Rational Design Study on 6,8-Substituted Luminol Derivatives
AU - Mikroulis, T.
AU - Cuquerella, M.C.
AU - Giussani, A.
AU - Pantelia, A.
AU - Rodríguez-Muñiz, G.M.
AU - Rotas, G.
AU - Roca-Sanjuán, D.
AU - Miranda, M.A.
AU - Vougioukalakis, G.C.
JO - The Journal of Organic Chemistry
PY - 2021
VL - 86
TODO - 17
SP - 11388-11398
PB - American Chemical Society
SN - null
TODO - 10.1021/acs.joc.1c00890
TODO - Efficiency;  Photophysics;  Quantum chemistry, Aromatic rings;  Derivatizations;  Luminols;  pH value;  Quantum chemistry computations;  Rational design;  Substitution patterns;  Systematic study, Chemiluminescence
TODO - 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. © 2021 American Chemical Society.
ER -