Synthesis and spectroscopic properties of 2-ketopyrrole–BF2 complexes: a new class of fluorescent dye

Chen, Jiong; Burghart, Armin; Wan, Chi-Wai; Thai, Long; Ortiz, Cesar G.; Reibenspies, Joseph; Burgess, Kevin

doi:10.1016/s0040-4039(00)00166-0

Cited by 43 publications

(21 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The intensity of the band at λ max = 272 nm ( ϵ max = 7.5 × 10 3 M –1 cm –1 ) is considerably less. Both these absorption bands are consistent with the spectrum of previous difluoropyrrolo‐oxaborole derivatives 5,6. Also prominent in the spectrum is a broad featureless band in the region 500–650 nm, which must arise from the perturbed ferrocene group.…”

Section: Resultssupporting

confidence: 88%

“…The F–B–N bond angles are noticeably greater than the ideal 109.5° and the smallest angle is formed by the endocyclic N–B–O atoms. The bond lengths are quite similar to those found for the two other known literature structures containing the basic pyrroloxaborole ring 5,6. The C6–O bond length is certainly longer than expected for a formal double bond and is consistent with a shift in electron density towards the boron centre.…”

Section: Resultssupporting

confidence: 83%

“…It is noticeable that for the preparation of Bodipy derivatives, the half‐way product is the 2‐ketopyrrole, which is rarely isolated since it reacts further to form the dipyrromethane. Considering the N (pyrrole) and O (ketone) atoms are arranged to facilitate formation of a five‐membered ring adduct with BF 2 , it is surprising that only two examples have been discussed in the literature 5,6. In attempts to prepare a bis(Bodipy)ferrocene derivative we found that the bis(ketopyrrole) derivative 2 was produced instead7 and could be converted readily to the BF 2 adduct, FBF .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Molecular Structure and Properties of a Ferrocene‐Based Difluoropyrrolo‐Oxaborole Derivative

et al. 2014

View full text Add to dashboard Cite

Reaction of 1,1′‐ferrocenedicarbonyl chloride with 3‐ethyl‐2,4‐dimethylpyrrole in DCM produced the half‐way product, namely, the ferrocene bis(2‐ketopyrrole) derivative 2 and not the expected bis(dipyrromethene) compound. The 2‐ketopyrrole compound readily reacted with BF3·Et2O to produce the bis(difluoropyrrolo)‐oxaborole compound, FBF, as a red/brown solid which was characterised by X‐ray crystallography. 57Fe Mössbauer spectra for 2 and FBF were consistent with low‐spin iron(II) (d6) ferrocene derivatives. A cyclic voltammogram for 2 in acetonitrile revealed a reversible wave at +0.31 V vs. Fc+/Fc (ferrocene‐based) and an irreversible wave at –2.38 V vs. Fc+/Fc (ketopyrrole‐based). The electrochemical behaviour is severely perturbed by the chelation of the BF2 groups. Alterations to the electronic properties of 2 by formation of FBF are also evident in the absorption profiles. DFT calculations [B3PW91, 6‐31G(3df)] support the observed changes in the electrochemistry findings and the Mössbauer spectroscopic data.

show abstract

Section: Resultssupporting

confidence: 88%

Section: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Molecular Structure and Properties of a Ferrocene‐Based Difluoropyrrolo‐Oxaborole Derivative

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Materials: BODIPY dyes 1-3 (purity > 90 %) were synthesized according to standard methods [52,53] and identified by NMR spectroscopy. Details will be described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

Comparative Photostability Studies of BODIPY and Fluorescein Dyes by Using Fluorescence Correlation Spectroscopy

2008

View full text Add to dashboard Cite

In single-molecule applications, the photostability of fluorescent molecules is a key parameter. We apply fluorescence correlation spectroscopy to compare the photostability of four fluorescein and four borondipyrromethene (BODIPY) dyes of similar structure but different triplet yields. The latter class of dyes are more stable. In the kinetic analysis the, diffusion and photobleaching are treated as competitive processes. Corrections, which account for saturation and for experimental artefacts, are achieved solely by using experimental data. Photobleaching is found to occur mainly through the first excited singlet state S(1), in contrast to previous findings.

show abstract

“…The compound has very poor solubility in solvents such as chloroform, THF, benzene, toluene, and acetonitrile. In DMSO it undergoes dissociation and formation of a DMSO-solvated silicon complex, [6s] (d,7.4 Hz,4 H, oPh L ); 13 C NMR (100.1 MHz,[D 6 ]DMSO) : d = 12.4,13.3,13.9,16.9 (alkyl),34 (broad multiplet, ]DMSO), 129. 1,129.9,130.1,133.8,133.9,137.5,139.0,158.9,168.5 ppm (C=O);29 Si NMR (79,5 MHz,[D 6 ]DMSO): d = À175.5 ppm.…”

Section: Compoundmentioning

confidence: 99%

2‐Acylpyrroles as Mono‐anionic O,N‐Chelating Ligands in Silicon Coordination Chemistry

Kämpfe

Brendler

Kroke

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

Kryptopyrrole (2,4-dimethyl-3-ethylpyrrole) was acylated with, for example, benzoyl chloride to afford 2-benzoyl-3,5-dimethyl-4-ethylpyrrole (L(1)H). With SiCl4 this ligand reacts under liberation of HCl and formation of the complex L(1)2SiCl2. In related reactions with HSiCl3 or H2SiCl2, the same chlorosilicon complex is formed under liberation of HCl and H2 or liberation of H2, respectively. The chlorine atoms of L(1)2SiCl2 can be replaced by fluoride and triflate using ZnF2 and Me3Si-OTf, respectively. The use of a supporting base (triethylamine) is required for the complexation of phenyltrichlorosilane and diphenyldichlorosilane. The complexes L(1)2SiCl2, L(1)2SiF2, L(1)2Si(OTf)2, L(1)2SiPhCl, and L(1)2SiPh2 exhibit various configurations of the octahedral silicon coordination spheres (i.e. cis or trans configuration of the monodentate substituents, different orientations of the bidentate chelating ligands relative to each other). Furthermore, cationic silicon complexes L(1)3Si(+) and L(1) SiPh(+) were synthesized by chloride abstraction with GaCl3. In contrast, reaction of L(1)2SiCl2 with a third equivalent of L(1)H in the presence of excess triethylamine produced a charge-neutral hexacoordinate Si complex with a new tetradentate chelating ligand which formed by Si-templated C-C coupling of two ligands L(1).

show abstract

Synthesis and spectroscopic properties of 2-ketopyrrole–BF2 complexes: a new class of fluorescent dye

Cited by 43 publications

References 7 publications

Synthesis, Molecular Structure and Properties of a Ferrocene‐Based Difluoropyrrolo‐Oxaborole Derivative

Synthesis, Molecular Structure and Properties of a Ferrocene‐Based Difluoropyrrolo‐Oxaborole Derivative

Comparative Photostability Studies of BODIPY and Fluorescein Dyes by Using Fluorescence Correlation Spectroscopy

2‐Acylpyrroles as Mono‐anionic O,N‐Chelating Ligands in Silicon Coordination Chemistry

Contact Info

Product

Resources

About