P. Wessig, M. Gerngroß, D. Freyse, P. Bruhns, M. Przezdziak, U. Schilde, A. Kelling
Molecular Rods Based on Oligo-spiro-thioketals
J. Org. Chem. 2016, 81, 1125
DOI: 10.1021/acs.joc.5b02670
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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