Vinamidin‐Chelate des Bors

Kühn, Norbert; Kuhn, Annette; Speis, M.; Bläser, Dieter; Boese, Roland

doi:10.1002/cber.19901230613

Cited by 27 publications

(18 citation statements)

References 31 publications

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“…Figure 1 shows that the angles of N1-B1-N2 and F1-B1-F2 in both compounds indicate a tetrahedral BF 2 N 2 configuration, and are within the range of the published data. [13,14] The average bond length of N1 À C1 indicates double-bond character, compared with the single-bond character of N1 À C4. For both compounds, there is strong pelectron delocalization between the central six-membered ring and the two adjacent pyrrole rings.…”

Section: Resultsmentioning

confidence: 99%

Conformationally Restricted Dipyrromethene Boron Difluoride (BODIPY) Dyes: Highly Fluorescent, Multicolored Probes for Cellular Imaging

Zheng¹,

Xu²,

Prasad³

2008

Chemistry A European J

196

108

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Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso-position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near-IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two-photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two-photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one- and two-photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated.

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Section: Resultsmentioning

confidence: 99%

Conformationally Restricted Dipyrromethene Boron Difluoride (BODIPY) Dyes: Highly Fluorescent, Multicolored Probes for Cellular Imaging

Zheng¹,

Xu²,

Prasad³

2008

Chemistry A European J

196

108

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“…X-ray structure analysis: Singlecrystal X-ray structures were obtained for compounds 3 a,c-e, 4 a, and 4 d and the basic features are listed in [32] 2,2-difluoro-1,3,4,6-tetramethyl-3-aza-1-azonia-2-borata-4,6-cyclohexadiene, [33] and 2,2-difluoro-4,6-dimethyl-1,3-di-p-toluyl-3-aza-1-azonia-2-boracyclohexa-4,6-dione. [34] With regard to the prerequisites for the general spectroscopic features as well as the charge-transfer characteristics of such highly internally twisted composite chromophores, the conjugation and the planarity within the molecular fragment are important.…”

mentioning

confidence: 99%

Boron–Diindomethene (BDI) Dyes and Their Tetrahydrobicyclo Precursors—en Route to a New Class of Highly Emissive Fluorophores for the Red Spectral Range

Shen

Röhr

Rurack

et al. 2004

Chemistry A European J

219

157

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The X-ray crystallographic, optical spectroscopic, and electrochemical properties of a newly synthesized class of boron-diindomethene (BDI) dyes and their tetrahydrobicyclo precursors (bc-BDP) are presented. The BDI chromophore was designed to show intensive absorption and strong fluorescence in an applicationary advantageous spectral range. Its modular architecture permits fusion of a second subunit, for example, a receptor moiety to the dye's core to yield directly linked yet perpendicularly prearranged composite systems. The synthesis was developed to allow facile tuning of the chromophore platform and to thus adjust its redox properties. X-ray analysis revealed a pronounced planarity of the chromophore in the case of the BDIs, which led to a remarkable close packing in the crystal of the simplest derivative. On the other hand, deviation from planarity was found for the diester-substituted bc-BDP benzocrown that exhibits a "butterfly"-like conformation in the crystal. Both families of dyes show charge- or electron-transfer-type fluorescence-quenching characteristics in polar solvents when equipped with a strong donor in the meso-position of the core. These processes can be utilized for signaling purposes if an appropriate receptor is introduced. Further modification of the chromophore can invoke such a guest-responsive intramolecular quenching process, also for receptor groups of low electron density, for example, benzocrowns. In addition to the design of various prototype molecules, a promising fluoroionophore for Na+ was obtained that absorbs and emits in the 650 nm region and shows a strong fluorescence enhancement upon analyte binding. Furthermore, investigation of the remarkable solvatokinetic fluorescence properties of the "butterfly"-like bc-BDP derivatives suggested that a second intrinsic nonradiative deactivation channel can play a role in the photophysics of boron-dipyrromethene dyes.

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“…In contrast to their ketiminato and diketonato analogues, complexes of the type Vin 3 M are unknown, as yet. In the course of our investigations on vinamidine [19,20] aluminum chelates [1,2,21,22] we have tried to fill this gap, and present now the first tris(diketiminato)metal complex.…”

Section: Introductionmentioning

confidence: 99%