CuII-selective bispidine–dye conjugates

Brox, Dominik; Comba, Peter; Herten, Dirk‐Peter; Kimmle, Esther; Morgen, Michael; Rühl, Carmen L.; Rybina, Arina; Stephan, Holger; Storch, Golo; Wadepohl, Hubert

doi:10.1016/j.jinorgbio.2015.05.009

Cited by 11 publications

(6 citation statements)

References 22 publications

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“…1 Based on the possibility to enforce specific coordination geometries and therefore stabilize complexes with specific properties, 2,3 the bispidine transition metal coordination chemistry has developed into a particularly broad field, with applications in catalytic aziridination, [4][5][6] sulfoxidation [7][8][9] and C-H-activation processes, [10][11][12] molecular magnetism, [13][14][15][16] the development of new ionophores, 17 radiotracers for positron emission tomography (PET), [18][19][20] and copper sensors. 21,22 Typical bispidine ligands and the main structural features of their transition metal complexes are shown in Chart 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and transition metal coordination chemistry of a novel hexadentate bispidine ligand

2015

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Reported is the new bispidine-derived hexadentate ligand (L = 3-(2-methylpyridyl)-7-(bis-2-methylpyridyl)-3,7-diazabicyclo[3.3.1]nonane) with two tertiary amine and four pyridine donor groups. This ligand can form heterodinuclear and mononuclear complexes and, in the mononuclear compounds discussed here, the ligand may coordinate as a pentadentate ligand, with one of the bispyridinemethane-based pyridine groups un- or semi-coordinated, or as a hexadentate ligand, leading to a pentagonal pyramidal coordination geometry or, with an additional monodentate ligand, to a heptacoordinate pentagonal bipyramidal structure. The solution and solid state data presented here indicate that, with the relatively small Cu(II) and high-spin Fe(II) ions the fourth pyridine group is only semi-coordinated for steric reasons and, with the larger high-spin Mn(II) ion genuine heptacoordination is observed but with a relatively large distortion in the pentagonal equatorial plane.

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Section: Introductionmentioning

confidence: 99%

Synthesis and transition metal coordination chemistry of a novel hexadentate bispidine ligand

2015

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“…In previous studies of similar probes, we have observed comparable effects and could exclude energy transfer as possible quenching mechanism. We found that the overlap between dye emission and ligand/complex absorption was too small to enable energy transfer , . However, as complex and chromophoric centers were always in close proximity, as is the case for BODIPY‐BPY 1 , photo‐induced electron transfer (PET) remains as possible quenching mechanism.…”

Section: Discussionmentioning

confidence: 94%

“…In previous studies, the bidentate bipyridine was found a suitable ligand for designed Cu II ‐dependent switchable fluorescent probes , . Therefore, we designed a bipyridine functionalized turn‐off probe with the shortest possible distance to the chromophore to maximize quenching upon coordination of Cu II .…”

Section: Introductionmentioning

confidence: 99%

Copper(II)‐induced Fluorescence Quenching of a BODIPY Fluorophore

Herten

Haderspeck

Braun

et al. 2018

Zeitschrift anorg allge chemie

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The ongoing developments in fluorescence microscopy have pushed the interest in new fluorescent probes with specific properties. Aside of controlling emissive states by light irradiation, defined control by changing the chemical environment has come into focus. In this context, we designed a fluorescent probe by conjugation of bipyridine, acting as sensor for CuII, to a BODIPY derivative at the shortest possible distance between sensor and chromophore. Herein, we present the synthesis of the BODIPY probe along with its crystal structure. We found a strong dependence of absorption and emission upon CuII complex formation decreasing the fluorescence quantum yield to ca. 1 % in respect to the pure probe. We hypothesize that further functionalization with a linker could make this compound and interesting probe for fluorescence microscopy.

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“…This could be achieved at the ligand-design stage, which includes the choice of the central diazacore, the nature (Q’s) and length (k’s) of the pendant arms, and that of the cyclizing bridge (n’s). In the context of this challenge, we noted with interest complexes of tetradentate bispidine-based ligands, studied mostly by Comba et al. − Recently, bispidines themselves proved to be privileged structures in medicinal chemistry . The rigid framework of bispidines in double-chair conformation allows them to be used to study the binding of small cations for a long time .…”

Section: Introductionmentioning

confidence: 99%

Copper–Bispidine Complexes: Synthesis and Complex Stability Study

et al. 2016

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A new series of dicarboxylic derivatives of bispidines have been synthesized to develop novel copper(II) complexes suitable as imaging agents for positron emission tomography. For characterization purposes, copper complexes of bispidines were synthesized in the pure form and in quantitative yields by neutralization of ligands with malachite. The formation of complexes and their stoichiometries were studied by potentiometric titration, cyclic voltammetry, and spectroscopic methods. The stability constants were found to be fairly suitable for copper cation fixation inside dianionic chelate molecules.

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CuII-selective bispidine–dye conjugates

Cited by 11 publications

References 22 publications

Synthesis and transition metal coordination chemistry of a novel hexadentate bispidine ligand

Synthesis and transition metal coordination chemistry of a novel hexadentate bispidine ligand

Copper(II)‐induced Fluorescence Quenching of a BODIPY Fluorophore

Copper–Bispidine Complexes: Synthesis and Complex Stability Study

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