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

Jiménez, Vicente G.; Santos, Fábio M. F.; Castro‐Fernández, Silvia; Cuerva, Juan M.; Góis, Pedro M. P.; Pischel, Uwe; Campaña, Araceli G.

doi:10.1021/acs.joc.8b01844

Cited by 29 publications

(14 citation statements)

References 60 publications

(95 reference statements)

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“…The conjugation of BAs with Schiff-base ligands enabled the construction of innovative boronic acid salicylidenehydrazone (BASHY) dyes with suitable structural and photophysical properties for live cell bioimaging applications that can be fine-tuned with simple structural modifications. [192][193][194][195][196] These dyes were employed by Gois, Bernardes and co-workers to site-selectively label Annexin V, an early marker of apoptosis, through maleimide technology for the detection of apoptotic cells. The BASHY dye maintained its photochemical and photophysical properties while attached to the biomolecules and the conjugate successfully targeted and detected the apoptotic cells, highlighting BASHY's utility as a promising fluorescent marker for biological imaging (Fig.…”

Section: Multivalent Boron Complexesmentioning

confidence: 99%

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

et al. 2019

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Section: Multivalent Boron Complexesmentioning

confidence: 99%

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

et al. 2019

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“…Hence, to demonstrate the feasibility of the azomethine structure as an acceptor in polymeric systems, we constructed a series of copolymers with fluorene and bithiophene donors and evaluated their electronic properties. Several researches based on complexation of azomethine and the boron atom were reported; however, to the best of our knowledge, there were no studies about an electron-accepting conjugated polymer scaffold. − …”

Section: Introductionmentioning

confidence: 99%

Construction of the Luminescent Donor–Acceptor Conjugated Systems Based on Boron-Fused Azomethine Acceptor

et al. 2019

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We report the boron-fused acceptor compound involving the azomethine structure prepared through the facile synthetic method. Additionally, we constructed the donor− acceptor (D−A) conjugated polymers which have the boronfused azomethine acceptors in the main chains. Cyclic voltammetry revealed that the electron-accepting ability was enhanced by boron coordination. Because of the strong D−A interaction, the conjugated polymers showed significant redshifts of optical bands both in the UV−vis absorption and PL spectra. Moreover, these polymers exhibited intense emission in both the solution and film states; meanwhile, the monomeric unit or non-boron-containing model polymers showed weak emission. It is suggested that these highly efficient emissive properties should be caused not only by the rigid skeleton but also by the strong D−A conjugated system originating from the boron-fused structure. This paper demonstrates that the combination of the azomethine structure and boron atom should be a promising strategy for obtaining an accepting monomeric unit, leading to luminescent conjugated polymer materials.

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“…So far, only a handful of configurationally stable tetracoordinate boron-stereogenic compounds have been reported, mainly as racemic mixtures. Methods to access enantioenriched boron-stereogenic compounds are restricted to resolution or a stoichiometric chiral substrate-induced diastereoselective approach (Scheme b). − To the best of our knowledge, catalytic asymmetric synthesis of enantioenriched boron-stereogenic compounds has remained unknown to date. Given their unique optoelectronic properties and versatile synthetic applications, expanding the chemical space of boron-stereogenic compounds and development of efficient asymmetric catalysis for the facile construction of boron-stereogenic centers are highly desirable.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective Construction of Chiroptical Boron-Stereogenic Compounds

Guo

2021

J. Am. Chem. Soc.

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The construction of main group heteroatom-stereogenic compounds is of great importance due to their intriguing chemical, physical, biological, and stereoelectronic properties. Despite that organoboron compounds are widely used in organic chemistry, the creation of a tetrahedral boron-stereogenic center in one enantiomeric form remains highly challenging. Given the labile nature of ligands attached to the tetracoordinate boron atom, only a handful of enantioenriched boron-stereogenic compounds have been reported via resolution or a chiral substrate-induced diastereoselective approach. To date catalytic asymmetric synthesis of boron-stereogenic compounds has remained unknown. Here, we demonstrate the first catalytic enantioselective construction of boron-stereogenic compounds via an asymmetric copper-catalyzed azide−alkyne cycloaddition (CuAAC) reaction. This enantioselective CuAAC reaction not only gives access to a wide range of novel highly functionalized boron-stereogenic heterocycles in high yields with good to excellent enantioselectivities but also produces optically active terminal alkyne and triazole moieties with various potential application prospects. Further transformation of the chiral tetracoordinate boron compounds delivers several complex heterocyclic entities bearing boron-stereogenic centers without the loss of enantiopurity. Moreover, the X-ray structure, the barrier to racemization, and the HOMO/LUMO gap of selected tetracoordinate boron compounds are investigated. Notably, these novel N,N π-conjugated boron-stereogenic compounds exhibit bright fluorescence. The optical properties, including circular dichroism, quantum yield, and circular polarized luminescence spectroscopies, are examined. These features expand the chemical space of the chiroptical boron-based dye platform, which could have great potential applications in chiral optoelectronic materials.

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

Cited by 29 publications

References 60 publications

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

Boronic acids as building blocks for the construction of therapeutically useful bioconjugates

Construction of the Luminescent Donor–Acceptor Conjugated Systems Based on Boron-Fused Azomethine Acceptor

Catalytic Enantioselective Construction of Chiroptical Boron-Stereogenic Compounds

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