Improved, Odorless Access to Benzo[1,2-d;4,5-d′]- bis[1,3]dithioles and Tert-butyl Arylsulfides via C-S Cross Coupling

Kopp, Kevin; Schiemann, Olav; Fleck, Nico

doi:10.3390/molecules25163666

Cited by 6 publications

(7 citation statements)

References 47 publications

(56 reference statements)

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“…The synthesis of Ox-SLIM 9C needs aryl building block 10, which can be obtained via two alternative routes from bisthioketal 11 [3,37] (Scheme 2). The first route starts with aromatic tri-methylsilylation of 11 by reactionw ith lithium tetramethylpiperide (LiTMP) and in situ quenching with trimethylsilyl chloride.…”

Section: Resultsmentioning

confidence: 99%

Ox‐SLIM: Synthesis of and Site‐Specific Labelling with a Highly Hydrophilic Trityl Spin Label

Fleck

Heubach

Hett

et al. 2021

Chemistry A European J

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The combination of pulsed dipolar electron paramagnetic resonance spectroscopy (PDS) with site‐directed spin labelling is a powerful tool in structural biology. Rational design of trityl‐based spin labels has enabled studying biomolecular structures at room temperature and within cells. However, most current trityl spin labels suffer either from aggregation with proteins due to their hydrophobicity, or from bioconjugation groups not suitable for in‐cell measurements. Therefore, we introduce here the highly hydrophilic trityl spin label Ox‐SLIM. Engineered as a short‐linked maleimide, it combines the most recent developments in one single molecule, as it does not aggregate with proteins, exhibits high resistance under in‐cell conditions, provides a short linker, and allows for selective and efficient spin labelling via cysteines. Beyond establishing synthetic access to Ox‐SLIM, its suitability as a spin label is illustrated and ultimately, highly sensitive PDS measurements are presented down to protein concentrations as low as 45 nm resolving interspin distances of up to 5.5 nm.

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Section: Resultsmentioning

confidence: 99%

Ox‐SLIM: Synthesis of and Site‐Specific Labelling with a Highly Hydrophilic Trityl Spin Label

Fleck

Heubach

Hett

et al. 2021

Chemistry A European J

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“…(iii) 1. n-BuLi/THF, 2. ethyl chloroformate, 78%. (iv) TFA/H 2 O (5:1), 68% (28), 99% (30). (v) 1. n-BuLi/THF, 2.…”

Section: Short Review Synthesismentioning

confidence: 99%

“…Recently, a powerful alternative has been developed starting with 1,2,4,5-tetrabromobenzene (31b) and using S-tert-butylisothiouronium bromide/Pdcatalysis (Method B). 28 The installation of EWGs at S 4 -DBD dyes turned out to be more difficult than with O 4 -DBD dyes. While dialdehyde 34 and diester 36a were readily accessible, 29 attempts to directly prepare ketones from lithiated 33 have failed so far.…”

Section: S 4 -Dbd Dyesmentioning

confidence: 99%

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

Wessig¹,

Lehmann²

2023

Synthesis

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In this review we give an overview of the syntheses and photophysical properties of the new class of fluorescent dyes based on a [1,3]-dioxolo[4,5-f]benzodioxole core and their derivatives. Starting from commercially available reactants (e.g., sesamol, 1,2,4,5-tetrachlorobenzene) the core units can be prepared in a simple manner. Then, the benzene core can be derivatized via lithiation and their photophysical properties can be adjusted as desired. The obtained fluorophores have an absorption range of 403–520 nm and an emission range of 495–665 nm. This class of fluorescent dyes is also characterized by a long fluorescence lifetime, a high stability towards photobleaching, large Stokes shifts, and small size. Thus, the DBD dyes are optimally suited for optical sensing.1 Introduction2 Synthesis3 Properties4 Applications

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“…Moreover, the quite efficient synthesis of S 4 ‐DBD dyes mandatorily requires the use of extremely malodorous tert ‐butylthiol [7a] . It should be noted that very recently an alternative route has been published [7d] . Therefore we hypothesized that the replacement of already less than four sulfur atoms could satisfactorily improve the spectroscopic and synthetic issues.…”

Section: Introductionmentioning

confidence: 99%

Sulfur Tuning of [1,3]‐Dioxolo[4.5‐f]benzodioxole (DBD) Fluorescent Dyes

et al. 2020

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Dedicated to Professor Bernd Giese on the occasion of his 80th birthday. The replacement of oxygen by sulfur atoms of [1,3]-dioxolo[4.5f]benzodioxole (DBD) fluorescent dyes is an efficient way to adjust the photophysical properties (sulfur tuning). While previously developed S 4-DBD dyes exhibit considerably redshifted absorption and emission wavelength, the heavy atom effect of four sulfur atoms cause low fluorescence quantum yields and short fluorescence lifetimes. Herein, we demonstrate that the replacement of less than four sulfur atoms (S 1-DBD, 1,2-S 2-DBD, and 1,4-S 2-DBD dyes) permits a fine-tuning of the photophysical properties. In some cases, a similar influence on the wavelength without the detrimental effect on the quantum yields and lifetimes is observed. Furthermore, the synthetic accessibility of S 1-and S 2-DBD dyes is improved, compared with S 4-DBD dyes. For coupling with biomolecules a series of reactive derivatives of the new dyes were developed (azides, OSu esters, alkynes, maleimides).

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Improved, Odorless Access to Benzo[1,2-d;4,5-d′]- bis[1,3]dithioles and Tert-butyl Arylsulfides via C-S Cross Coupling

Cited by 6 publications

References 47 publications

Ox‐SLIM: Synthesis of and Site‐Specific Labelling with a Highly Hydrophilic Trityl Spin Label

Ox‐SLIM: Synthesis of and Site‐Specific Labelling with a Highly Hydrophilic Trityl Spin Label

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

Sulfur Tuning of [1,3]‐Dioxolo[4.5‐f]benzodioxole (DBD) Fluorescent Dyes

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