4′,4″(5″)-Di-tert-butyldibenzo-18-crown-6 is a hydrophobic crown
ether compound. This crown ether is potentially useful in studies of ion
transport through non-polar regions and membranes, and has been
described in the design of microsensor devices for ammonia determination
based upon ammonia-mediated deprotonation of a pH indicator followed by
sequestering of ammonium within the
4′,4″(5″)-Di-tert-butyldibenzo-18-crown-6 sphere.
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Off-white powder
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4'',4''''(5'''')-Di-tert-butyldibenzo-18-crown-6 is a hydrophobic crown ether compound..
Synthesis
4',4''(5'')-Di-tert-butyldibenzo-18-crown-6 (DTBB18C6) was synthesized using 4-tert-butyl catechol (TBC) as starting material, 2,2′-diethylene glycol di(p-touenesulfonate) as cyclization reagent, Cs2CO3 as template, and tetrahydrofuran (THF) as solvent. The reaction was carried out in a sealed environment with nitrogen, and Cs2CO3 was supplemented in three steps. Moreover, it could also be synthesized by improving the electrophilic aromatic substitution of dibenzo-18-crown-6 (DB18C6) using tert-butyl alcohol (TBA) as alkylation reagent, H3PO4 (85 wt %) as catalyst and CH2Cl2 as solvent[1-2].
