TY  - JOUR
A1  - Wessig, Pablo
A1  - Gerngross, Maik
A1  - Freyse, Daniel
A1  - Bruhn, P.
A1  - Przezdziak, Marc
A1  - Schilde, Uwe
A1  - Kelling, Alexandra
T1  - Molecular Rods Based on Oligo-spiro-thioketals
JF  - The journal of organic chemistry
N2  - 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.
Y1  - 2016
U6  - https://doi.org/10.1021/acs.joc.5b02670
SN  - 0022-3263
VL  - 81
SP  - 1125
EP  - 1136
PB  - American Chemical Society
CY  - Washington
ER  -