RT Journal Article
T1 Azaborahelicene fluorophores derived from four-coordinate N,C-boron chelates: synthesis, photophysical and chiroptical properties
A1 Vázquez Domínguez, Pablo
A1 Rizo, José Francisco
A1 Fernández Arteaga, Jesús
A1 Jacquemin, Denis
A1 Favereau, Ludovic
A1 Ros, Abel
A1 Pischel, Uwe
AB A series of six azaborahelicenes with varying electron-donor substitution at the 4-position of the aryl residue (i.e., naphthyl) or with variable π-extension of the aryl residue (thianthrenyl, anthryl, pyrenyl) was prepared with an efficient and flexible synthetic protocol. These different types of functionalization afforded notably pronounced intramolecular charge-transfer (ICT) character for the dyes with the strongest electron donor substitution (NMe2) or easiest to oxidize aryl residues, as evidenced by photophysical investigations. These effects also impact the corresponding chiroptical properties of the separated M- and P-enantiomers, which notably display circularly polarized luminescence (CPL) with dissymmetry factors in the order of magnitude of 10−4 to 10−3. Theoretical calculations confirm the optical spectroscopy data and are in agreement with the proposed involvement of ICT processes.
PB Royal Society of Chemistry (RSC)
SN 2052-4129 (electrónico)
YR 2024
FD 2024-01
LK https://hdl.handle.net/10272/23277
UL https://hdl.handle.net/10272/23277
LA eng
NO Vázquez-Domínguez, P., Rizo, J. F., Arteaga, J. F., Jacquemin, D., Favereau, L., Ros, A., & Pischel, U. (2024). Azaborahelicene fluorophores derived from four-coordinate N,C-boron chelates: synthesis, photophysical and chiroptical properties. In Organic Chemistry Frontiers (Vol. 11, Issue 3, pp. 843–853). Royal Society of Chemistry (RSC). https://doi.org/10.1039/d3qo01762a
NO We thank the Spanish Ministerio de Ciencia e Innovación for financial support (grant PID2020-119992GB-I00 for U. P., PID2019-106358GB-C21 for A. R., and doctoral fellowship PRE2020-092646 for P. V.-D.). Further, U. P. received funding from the University of Huelva/European Research and Development Fund (ERDF); project UHU-202070. A. R. is grateful to the Consejo Superior de Investigaciones Científicas (CSIC, grant 202080I005). D. J. is indebted to the CCIPL/Glicid computational center installed in Nantes for generous allocation of computational resources. This project is co-funded by the European Union (ERC), SHIFUMI, 101041516 (L. F.). Views and opinions expressed are however those of the author(s) only and do not necessarily reflect those of the European Union or the European Research Council. Neither the European Union nor the granting authority can be held responsible for them. We also thank Dr F. J. Fernández de Córdova (Institute for Chemical Research – CSIC, Seville) for the X-ray structure analysis.
DS Repositorio Institucional de la Universidad de Huelva
RD 31 may 2026