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Wessig P, Gerngroß M, Freyse D, et al. Molecular Rods Based on Oligo-spiro-thioketals. J Org Chem. 2016;81(3):1125-36doi: 10.1021/acs.joc.5b02670.
Wessig, P., Gerngroß, M., Freyse, D., Bruhns, P., Przezdziak, M., Schilde, U., & Kelling, A. (2016). Molecular Rods Based on Oligo-spiro-thioketals. The Journal of organic chemistry, 81(3), 1125-36. https://doi.org/10.1021/acs.joc.5b02670
Wessig, P, et al. "Molecular Rods Based on Oligo-spiro-thioketals." The Journal of organic chemistry vol. 81,3 (2016): 1125-36. doi: https://doi.org/10.1021/acs.joc.5b02670
Wessig P, Gerngroß M, Freyse D, Bruhns P, Przezdziak M, Schilde U, Kelling A. Molecular Rods Based on Oligo-spiro-thioketals. J Org Chem. 2016 Feb 05;81(3):1125-36. doi: 10.1021/acs.joc.5b02670. Epub 2016 Jan 25. PMID: 26756391.
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J Org Chem. 2016 Feb 05;81(3):1125-36. doi: 10.1021/acs.joc.5b02670. Epub 2016 Jan 25.

Molecular Rods Based on Oligo-spiro-thioketals.

The Journal of organic chemistry

P Wessig, M Gerngroß, D Freyse, P Bruhns, M Przezdziak, U Schilde, A Kelling

Affiliations

  1. Institut für Chemie, Universität Potsdam , Karl-Liebknecht-Strasse 24-25, D-14476 Potsdam, Germany.

PMID: 26756391 DOI: 10.1021/acs.joc.5b02670

Abstract

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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