Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

Wessig, Pablo; Merkel, Roswitha; Müller, Peter

doi:10.3762/bjoc.11.11

Cited by 7 publications

(7 citation statements)

References 25 publications

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“…To sum up, the highest selectivity was achieved with the Cu/C catalyst B . It should be noted that we obtained similar results very recently in connection with the synthesis of molecular rods 23…”

Section: Resultssupporting

confidence: 79%

Dendrimers with Oligospiroketal (OSK) Building Blocks: Synthesis and Properties

Wessig

Budach

Thünemann

2015

Chemistry A European J

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The development of novel dendrimers containing oligospiroketal (OSK) rods as building blocks is described. The linkage between the core unit (CU), branching units (BU), and OSK rods relies on the CuAAC reaction between terminal alkynes and azides. Two different strategies of dendrimer synthesis were investigated and it was found that the convergent approach is clearly superior to the divergent one. SAXS measurements and MD simulations indicate that the obtained dendrimer features a globular structure with very low density. Obviously, the OSK rods stabilize a rather loose mass-fractal structure.

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Section: Resultssupporting

confidence: 79%

Dendrimers with Oligospiroketal (OSK) Building Blocks: Synthesis and Properties

Wessig

Budach

Thünemann

2015

Chemistry A European J

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“…The previously developed oligospiroketal (OSK) rods proved to be versatile molecular rods. − However, the length of these rods is limited due to the lability of acetals during the synthesis and the reversibility of the formation reaction. On the other hand, it is well known that thioacetals are much more stable, and the formation reaction is not reversible.…”

Section: Discussionmentioning

confidence: 99%

“…Recently, we used OSK rods as building blocks in porous materials and dendrimers . It should be noted that the solubility is also improved by incorporating a flexible joint, leading to articulated rods …”

Section: Introductionmentioning

confidence: 99%

Molecular Rods Based on Oligo-spiro-thioketals

et al. 2016

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We report on an extension of the previously established concept of oligospiroketal (OSK) rods by replacing a part or all ketal moieties by thioketals leading to oligospirothioketal (OSTK) rods. In this way, some crucial problems arising from the reversible formation of ketals are circumvented. Furthermore, the stability of the rods toward hydrolysis is considerably improved. To successfully implement this concept, we first developed a number of new oligothiol building blocks and improved the synthetic accessibility of known oligothiols, respectively. Another advantage of thioacetals is that terephthalaldehyde (TAA) sleeves, which are too flexible in the case of acetals can be used in OSTK rods. The viability of the OSTK approach was demonstrated by the successful preparation of some OSTK rods with a length of some nanometers.

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“…As an extension of the OS(T)K concept, we are developing constructs in which two rigid rods are connected by a flexible joint. These molecules are called “articulated rods” and show the outstanding feature of conformational bistability, which is currently being explored for its application in optical-sensing probes …”

Section: Discussionmentioning

confidence: 99%

“…These molecules are called "articulated rods" and show the outstanding feature of conformational bistability, which is currently being explored for its application in optical-sensing probes. 45…”

Section: ■ Conclusionmentioning

confidence: 99%

Rigid Rod-Based FRET Probes for Membrane Sensing Applications

et al. 2016

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Oligospirothioketal (OSTK) rods are presented as an adjustable scaffold for optical membrane probes. The OSTK rods are readily incorporated into lipid bilayers due to their hydrophobic backbones. Because of their high length-over-diameter aspect ratio, only a minimal disturbance of the lipid bilayer is caused. OSTK rods show outstanding rigidity and allow defined labeling with fluorescent dyes, yielding full control of the orientation between the dye and OSTK skeleton. This allows the construction of novel Förster resonance energy transfer probes with highly defined relative orientations of the transition dipole moments of the donor and acceptor dyes and makes the class of OSTK probes a powerful, flexible toolbox for optical biosensing applications. Data on steady-state and time-resolved fluorescence experiments investigating the incorporation of coumarin- and [1,3]dioxolo[4,5-f][1,3]benzo-dioxole-labeled OSTKs in large unilamellar vesicles are presented as a show case.

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Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

Cited by 7 publications

References 25 publications

Dendrimers with Oligospiroketal (OSK) Building Blocks: Synthesis and Properties

Dendrimers with Oligospiroketal (OSK) Building Blocks: Synthesis and Properties

Molecular Rods Based on Oligo-spiro-thioketals

Rigid Rod-Based FRET Probes for Membrane Sensing Applications

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