RT Journal Article
T1 Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence
A1 Felicidade, João
A1 F. Santos, Fabio M.
A1 Fernández Arteaga, Jesús
A1 Remón Ruiz, Patricia
A1 Campos-González, René
A1 Nguyen, Ha-Chi
A1 Nájera, Francisco
A1 Boscá, Francisco
A1 Ng, David Y. W.
A1 P. Gois, Pedro M.
A1 Pischel, Uwe
AB A set of nine boronic-acid-derived salicylidenehydrazone (BASHY) complexes has been synthesized in good to very good chemical yields in a versatile three-component reaction. In an extension to previous reports on this dye platform, the focus was put on the electronic modification of the “vertical” positions of the salicylidenehydrazone backbone. This enabled the observation of fluorescence quenching by photoinduced electron transfer (PeT), which can be reverted by the addition of acid in organic solvent (OFF-ON fluorescence switching). The resulting emission is observed in the green-to-orange spectral region (maxima at 520–590 nm). In contrast, under physiological pH conditions in water, the PeT process is inherently decativated, thereby enabling theobservation of fluorescence in the red-to-NIR region (maxima at 650–680 nm) with appreciable quantum yields and lifetimes. The latter characteristic supported the application of the dyes in fluorescence lifetime imaging (FLIM) of live A549 cells.
PB Wiley
SN 0947-6539
SN 1521-3765 (electrónico)
YR 2023
FD 2023
LK https://hdl.handle.net/10272/22934
UL https://hdl.handle.net/10272/22934
LA eng
NO Felicidade, J., Santos, F. M. F., Arteaga, J. F., Remón, P., Campos‐González, R., Nguyen, H., Nájera, F., Boscá, F., Ng, D. Y. W., Gois, P. M. P., & Pischel, U. (2023). Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence. In Chemistry – A European Journal (Vol. 29, Issue 31). Wiley. https://doi.org/10.1002/chem.202300579
NO This work was generously supported by the Portuguese FundaçãoparaaCiênciaeTecnologia [grantsPTDC/QUI-OUT/ 3989/2021 (P.G.); institutional grants UIDB/04138/2020 and UIDP/04138/2020 (iMed)], theSpanishMinisteriodeCienciae Innovación [grants CTQ2017-89832-P, PID2020-119992GB-I00 (bothtoU.P.),andPID2019-104293GB-I00(F.N.)], theConsejería deUniversidad, Investigacióne Innovación/JuntadeAndalucía [grantP18-FR-4080(U.P.)],andtheUniversidaddeHuelva/Junta deAndalucía [UHU202070 (U.P.)]. TheNMRspectrometersare partofthePortugueseNationalNMRNetwork(PTNMR)andare partially supportedby Infrastructure Project No. 022161 (cofinancedbyFEDER throughCOMPETE2020, POCI, PORL, and FCTthroughPIDDAC).WealsoacknowledgetheSupercomputingandBioinformaticsCentre(SCBI)oftheUniversityofMálaga forprovidingthecomputer resourcesusedfor thetheoretical calculations.
DS Repositorio Institucional de la Universidad de Huelva
RD 31 may 2026