A Three‐Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes)

Abstract

How did the collaborationo nt his project start?As in many cases, it started with ameeting of the two corresponding authors at ac onference;i nt his particular case at the National Meeting of the Portuguese Society of Chemistry in Aveiro in the summer of 2013. The first discussions were driven by curiosity for each other's research and relatively fast it crystallized that there was am utual interest in fluorescent probes with potential applications in chemical biology.F rom there, it was short step to identifying the useful complementarities of the involved research groups. Geographical closeness, the common concerns of researchers that pursue their careers in the south of Europe, and personal sympathies helped to set up the collaboration with al ot of human quality (despite the support of rival football teams).

Photoswitchable Boronic Acid Derived Salicylidenehydrazone Enabled by Photochromic Spirooxazine and Fulgide Moieties: Multiple Responses of Optical Absorption, Fluorescence Emission, and Quadratic Nonlinear Optics

“…34 These enable them to achieve tailored physicochemical features without compromising functional diversity and thus play a vital role in biological imaging. 26,35 Our attention was drawn to the fluorescence fine-tuning groups at both ends of the π-conjugated backbone in BASHY dyes, which exhibits typical D−π−A architecture, and hence emission properties can be readily tailored to meet specific requirements (Figure 1, panel A). Such a standard paradigm also probably promotes NLO performance on which very few researches into BASHY dyes have been focused yet, to the best of our knowledge.…”

Fluorescence Quenching in BODIPY Dyes: The Role of Intramolecular Interactions and Charge Transfer

“…, was only reported in 2009), followed by an extensive synthetic efforts to functionalize the dye core and tune the chemical and photophysical properties . Alternatively, the success of BODIPY derivatives inspired the design of various similar compounds such as aza‐BODIPY, PODIPY, BODIHY, BOPHY, BOIMPY and others …”

Circularly Polarized Luminescence of Boronic Acid-Derived Salicylidenehydrazone Complexes Containing Chiral Boron as Stereogenic Unit

“…49−51 These dyes are part of the larger family of heterocyclic boronate complexes with a tetracoordinated (stereogenic) boron center. 52−57 Following our recently published work, 49,50 it can be affirmed that these fluorophores are strong light absorbers (∼50000−60000 M −1 cm −1 for the long-wavelength absorption band at ∼470 nm), emit with maxima between 500 and 600 nm, and have high quantum yields (Φ fluo ≈ 0.5−0.6) in nonpolar solvents. These complexes contain a single asymmetric boron center, and given the fact that we had focused so far on the racemic dyes, we became interested in separating the enantiomers and testing them as SOM-CPL systems.…”

“…For this purpose, we selected dyes 1−5 from a recently prepared and photophysically characterized larger pool of BASHY dyes; 50 see Figure 1. This selection was motivated by the previous observation 49,50 that the varying push−pull character of 1−4 allows for fine-tuning the emission wavelength of the racemic dyes and thus, would also provide a means to control the spectral position of the CPL signal. Dye 5 was chosen for being a BASHY dimer with two chiral boron centers, embracing the additional challenge of also separating the chiroptically inactive meso diastereoisomer.…”