A triply bridged triphenylmethyl dication {6,13,23,30,39,46-hexaoxaoctacyclo[16.16. 16.22,5.214,17.219,22.231,34. 235,38.247,50]dohexaconta-2,4,14,16,19,21,31,33,35,37,47, 49,51,53,55,57,59,61-octadecaene-8,10,25,27,41,43-hexayne-1,18-diyliumbis (tetrafluoroborate) 4} and its open-chained analogue 1,6-bis{4-[bis-(4-methoxyphenyl) methyl]phenoxy}hexa-2,4-diynediylium bis(tetrafluoroborate) (9) are synthesized by using a new variant of the Eglinton reaction. Compound 4 constitutes the first example of concave dyestuffs bearing a large rigid cavity.