Abstract
Physicochemical and, in particular, visual recognition of positional isomers, due to their similar appearance and properties, is an extremely challenging task. Here we present an easy-to-prepare assay for the naked-eye differentiation of all possible isomers of phthalic acids. The desired optical response is attained through specific non-covalent interactions between the acids and a cationic macrocyclic host. These interactions are then translated to and amplified by gold nanoparticles which subsequently aggregate to various extents producing a color palette.
Highlights
Mykola Kravets, a Grzegorz Sobczak, a Nazar Rad, a Iwona MisztalewskaTurkowicz, b Oksana Danylyuk a and Volodymyr Sashuk *a
The desired optical response is attained through specific non-covalent interactions between the acids and a cationic macrocyclic host
These interactions are translated to and amplified by gold nanoparticles which subsequently aggregate to various extents producing a color palette
Summary
Mykola Kravets, a Grzegorz Sobczak, a Nazar Rad, a Iwona MisztalewskaTurkowicz, b Oksana Danylyuk a and Volodymyr Sashuk *a. Pillar[n]pyridiniums (PPs) are a new family of prismatically shaped oligocationic macrocycles, introduced by us recently, capable of recognizing anionic species including carboxylic acids.[12,13] We noted that pillar[6]pyridinium (P6P), a midsized member of this class, it has no preference in binding phthalic isomers, with one of them (terephthalic acid) undergoes aggregation.[13] This strikingly differs it from the previous probes and was attributed to the opposite directionality of carboxylic groups that sewed the macrocycles into insoluble polymeric chains. The precipitation of terephthalic acid upon complexation was first described by the Sessler group for an imidazolium based cationic macrocycle known as a Texas-sized box.[14] the formation of a precipitate was observed only when terephthalic acid was in a monoprotonated form.
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