Efficient fluorophores based on pyridyl-enolato and enamido difluoroboron complexes: Simple alternatives to boron-dipyrromethene (bodipy) dyes

Kopacka, Holger; Wurst, Klaus; Ruetz, Markus; Kreutz, Christoph; Müller, Thomas; Hirtenlehner, Christa; Monkowius, Uwe; Knör, Günther; Bildstein, Benno

doi:10.1016/j.ica.2013.05.034

Cited by 17 publications

(11 citation statements)

References 16 publications

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“…Furthermore, it was implied that the nitrogen atom could contribute to suppressing ACQ by partially disordering π‐stacking at the boron complex moiety. Based on these results, we designed ketoiminate complexes by employing fused structures in order to realize constant emission efficiencies in the solid state, such as the amorphous and crystal forms, as well as in solution. By introducing the fused structure at the nitrogen atom in the ketoiminate ligand, molecular motions should be effectively suppressed.…”

Section: Resultsmentioning

confidence: 99%

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

2017

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Mechanochromic luminescent molecules often suffer from critical loss of luminescence intensity during phase transitions in the solid state. In this study, we present mechanochromic luminescent molecules that can provide clear color changes with constant emission intensity during phase transitions. It was reported that the class of aggregation‐induced emission (AIE)‐active boron complexes can present intense emission by freezing intramolecular motions. According to this mechanism, we designed a complex with a fused ligand to preserve the enhanced emission in the aggregated state in the AIE during phase transitions between the solution, amorphous, and crystalline states. From optical measurements, it was shown that the synthesized boron complexes present bright emission in various phases. In particular, as we expected, the luminescence color was clearly altered during phase transition, whereas the emission intensity changed only slightly. Finally, we also found that diverse luminescence colors were obtained from each polymorph and for various substituents as induced by the substituent effect. The results in the series of mechanistic studies show that electronic interactions and π–π interactions can modulate the electronic conjugation system of the complexes without causing loss of emission efficiency.

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Section: Resultsmentioning

confidence: 99%

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

2017

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“…Chemicals were obtained commercially and used as received. Spectroscopic characterization was performed as recently published 14a,14b. Cobaltocenium carboxylic acid hexafluorophosphate ( 1 ) was synthesized by our recently published method 2…”

Section: Methodsmentioning

confidence: 99%

Cobaltocenium Carboxylate Transition Metal Complexes: Synthesis, Structure, Reactivity, and Cytotoxicity

Vanicek

Kopacka

Wurst

et al. 2015

Zeitschrift anorg allge chemie

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Cobaltocenium carboxylate is an unusual betaine that functions as a formally neutral carboxylate ligand with late transition metal centers comprising Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, and Rh+. Structurally, a rich coordination chemistry is observed – from simple monomeric homoleptic complexes to heteroleptic dimeric, trimeric, and polymeric compounds, as shown by X‐ray diffraction of 11 compounds. Chemically, thermal decarboxylation was investigated aiming at the formation of cobaltocenium‐carbene transition metal complexes, in analogy to such chemistry of imidazolium carboxylate betaines. Cytotoxicity studies of cobaltocenium carboxylate transition metal complexes were performed to evaluate the medicinal bioorganometallic potential of these compounds. While cobaltocenium carboxylate was inactive, its complexes with Ag+, Cd2+, and Hg2+ triggered significant cytotoxic effects.

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“…A similar process allows obtaining boranil derivatives (Figure b). , However, in that event the proton of an OH group is substituted in the last step of the synthetic route leading to a N–B–O type linkage. Yet another class of compounds with BF 2 moiety are diketonates (Figure c) that also constitute an increasingly popular family, − whereas diiminates − (with BF 2 bonded to two nitrogen atoms) (Figure d) as well as ketoiminates − (Figure e) with unsymmetrically bonded BF 2 moiety have also been studied. Globally, the BF 2 -carrying molecules are the most popular organic fluorophores to date and, as Ziessel pointed out, they constitute an “El Dorado for fluorescence tools” .…”

Section: Introductionmentioning

confidence: 99%

Photophysical Properties of Phenacylphenantridine Difluoroboranyls: Effect of Substituent and Double Benzannulation

et al. 2017

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In this study we present a new series of phenantridine-based substituted difluoroboranyls. The effects of substitution and double benzannulation on their photophysical properties were examined with experimental techniques and compared with the results obtained for previously reported quinoline and isoquinoline derivatives. The experimental characterizations are supported by state-of-the-art quantum-chemical calculations. In particular, the theoretical calculations were performed to gain insights into the complex nature of the relevant excited-states. These calculations reveal that both the nature of the substituent and its position on the phenyl ring significantly impact the magnitude of the electronic charge transferred upon excitation. Additionally, vibrationally resolved spectra were determined allowing for the analysis of the key vibrations playing a role in the band shapes.

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Efficient fluorophores based on pyridyl-enolato and enamido difluoroboron complexes: Simple alternatives to boron-dipyrromethene (bodipy) dyes

Cited by 17 publications

References 16 publications

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

Cobaltocenium Carboxylate Transition Metal Complexes: Synthesis, Structure, Reactivity, and Cytotoxicity

Photophysical Properties of Phenacylphenantridine Difluoroboranyls: Effect of Substituent and Double Benzannulation

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