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Strapped calix[4]pyrroles bearing a 1,3-indanedione at a beta-pyrrolic position: chemodosimeters for the cyanide anion.

ABSTRACT: A strapped calix[4]pyrrole bearing a 1,3-indanedione group at a beta-pyrrolic position has been synthesized and studied as a ratiometric cyanide-selective chemosensor. A concentration-dependent bleaching of the initial yellow color was observed upon addition of the cyanide anion. The bleaching, which was observed exclusively with the cyanide anion, occurred even in the presence of other anions. Spectroscopic studies provide support for a mechanistic interpretation wherein the cyanide anion forms a complex with the receptor (K = 2.78 x 10(4) M(-1)) through a fast equilibrium, which is followed by slow nucleophilic addition to the beta-position of the 1,3-indanedione group. A minimum inhibitory effect from other anions was observed, a feature that could be beneficial in the selective sensing of the cyanide anion.

SUBMITTER: Kim SH

PROVIDER: S-EPMC4105216 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Strapped calix[4]pyrroles bearing a 1,3-indanedione at a beta-pyrrolic position: chemodosimeters for the cyanide anion.

Kim Sook-Hee SH Hong Seong-Jin SJ Yoo Jaeduk J Kim Sung Kuk SK Sessler Janathan L JL Lee Chang-Hee CH

Organic letters 20090801 16

A strapped calix[4]pyrrole bearing a 1,3-indanedione group at a beta-pyrrolic position has been synthesized and studied as a ratiometric cyanide-selective chemosensor. A concentration-dependent bleaching of the initial yellow color was observed upon addition of the cyanide anion. The bleaching, which was observed exclusively with the cyanide anion, occurred even in the presence of other anions. Spectroscopic studies provide support for a mechanistic interpretation wherein the cyanide anion forms ...[more]

PMID: 19639968

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Project description:The importance of noncovalent interactions in the realm of biological materials continues to inspire efforts to create artificial supramolecular polymeric architectures. These types of self-assembled materials hold great promise as environmentally stimuli-responsive materials because they are capable of adjusting their various structural parameters, such as chain length, architecture, conformation, and dynamics, to new surrounding environments upon exposure to appropriate external stimuli. Nevertheless, in spite of considerable advances in the area of responsive materials, it has proved challenging to create synthetic self-assembled materials that respond to highly disparate analytes and whose environmentally induced changes in structure can be followed directly through both various spectroscopic and X-ray diffraction analyses. Herein, we report a new set of artificial self-assembled materials obtained by simply mixing two appropriately chosen, heterocomplementary macrocyclic receptors, namely a tetrathiafulvalene-functionalized calix[4]pyrrole and a bis(dinitrophenyl)-meso-substituted calix[4]pyrrole. The resulting polymeric materials, stabilized by combination of donor-acceptor and hydrogen bonding interactions, undergo dynamic, reversible dual guest-dependent structural transformations upon exposure to two very different types of external chemical inputs, namely chloride anion and trinitrobenzene. The structure and dynamics of the copolymers and their analyte-dependent responsive behavior was established via single crystal X-ray crystallography, SEM, heterocomplementary isodesmic analysis, 1- and 2D NMR, and dynamic light scattering spectroscopies. Our results demonstrate the benefit of using designed heterocomplementary interactions of two functional macrocyclic receptors to create synthetic, self-assembled materials for the development of "smart" sensory materials that mimic the key biological attributes of multianalyte recognition and substrate-dependent multisignaling.

Dataset Information

Strapped calix[4]pyrroles bearing a 1,3-indanedione at a beta-pyrrolic position: chemodosimeters for the cyanide anion.

Publications

Strapped calix[4]pyrroles bearing a 1,3-indanedione at a beta-pyrrolic position: chemodosimeters for the cyanide anion.

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