Synthesis and Photophysical Behavior of a Highly FluorescentFamily of Unsymmetrical Organoboron Complexes Containing5‑(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties

Authors
Garre Hernández, María SoledadUniversity of Alcalá Author; Losantos, Raúl; Gutiérrez Hernández, SaraUniversity of Alcalá Author; Sucunza Sáenz, DavidUniversity of Alcalá Author; García García, PatriciaUniversity of Alcalá Author; [et al.]
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/43764
DOI: 10.1021/acs.joc.9b02451
ISSN: 0022-3263
Date
2020-01-17
Embargo end date
2021-01-18
Affiliation
Universidad de Alcalá. Departamento de Química Orgánica y Química Inorgánica
Bibliographic citation
Journal of Organic Chemistry, 2020, v. 85, n. 2, p. 441-448
Keywords
organoboron complexes
fluorescence
BF2 bridge
water solubility
Project
CTQ2017-85263-R and CTQ2017-87372-P (Ministerio de Ciencia, Innovación y Universidades, AEI, FEDER); ISCIII RETIC REDINREN RD16/0009/0015 (Instituto de Salud Carlos III, FEDER)
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
© 2019 American Chemical Society
Access rights
info:eu-repo/semantics/openAccess
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Abstract
A new and highly fluorescent family of unsymmetrical organoboron complexes containing 5-(pyridin-2-ylmethylene)imidazolidine-2,4-dione moieties has been synthesized in three steps. These compounds show strong absorptions covering a wide range of the UV-Vis spectrum and are strongly emissive (ff of up to 0.92 in CH3CN). Moreover, two fluorophores that include an alkyne or an azide group at the end of the alkyl chain, and with potential utility in bioorthogonal chemistry, have been developed. One of these, in which the glycol substituent provides an enhanced water solubility without compromising the fluorescence (ff = 0.85 in water), may be of particular importance.
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