Assembly and Exchange of Resorcinarene Capsules Monitored by Fluorescence Resonance Energy Transfer

Barrett, Elizabeth S.; Dale, Trevor J.; Rebek, Julius

doi:10.1021/ja0700956

Cited by 116 publications

(75 citation statements)

References 19 publications

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“…There has been much interest in the solution phase encapsulation behaviour of the C-alkylresorcin [4]arenes and C-alkylpyrogallol [4]arenes [105][106][107][108][109][110][111][112][113][114]. Of those (other than ourselves) who are interested in this area, the Rebek and Cohen groups have been most active in advancing the characterisation of these large non-covalent assemblies in the solution phase.…”

Section: Solution Based Assembly Of C-alkylresorcin[4]arenes and C-almentioning

confidence: 99%

“…In this regard, Rebek and co-workers have extensively studied the encapsulation of tetraalkylammonium salts, with more recent works focusing on the inclusion of glutaric acid and β-methyl d-glucopyranoside in resorcin [4]arene nano-capsules [109][110][111][112][113]. The same group has also recently synthesised resorcin [4]arenes that are selectively modified at the lower rim with probes, and the encapsulation of different probes can be followed using fluorescence resonance energy transfer [114]. By doing so, the authors of these papers have successfully utilised various NMR techniques to follow molecular encapsulation and self-assembly processes in these systems.…”

Section: Solution Based Assembly Of C-alkylresorcin[4]arenes and C-almentioning

confidence: 99%

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Metallo-supramolecular capsules

Dalgarno

Power

Atwood

2008

Coordination Chemistry Reviews

528

216

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Section: Solution Based Assembly Of C-alkylresorcin[4]arenes and C-almentioning

confidence: 99%

Section: Solution Based Assembly Of C-alkylresorcin[4]arenes and C-almentioning

confidence: 99%

Metallo-supramolecular capsules

Dalgarno

Power

Atwood

2008

Coordination Chemistry Reviews

528

216

View full text Add to dashboard Cite

“…These influences can be brought by charge transfer (CT) between electron‐poor and rich moieties, energy transfer (ET) between moieties with well‐overlapped spectra, and chirality transfer 25, 26, 27, 28, 29, 30. For instance, researchers[[qv: 25b,c]] utilized building blocks bearing naphthalene diimide and naphthalene moieties to flexibly control the coassembly/self‐sorting behavior.…”

Section: Introductionmentioning

confidence: 99%

Environment‐Adaptive Coassembly/Self‐Sorting and Stimulus‐Responsiveness Transfer Based on Cholesterol Building Blocks

Xing

Tham

et al. 2017

Advanced Science

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Manipulating the property transfer in nanosystems is a challenging task since it requires switchable molecular packing such as separate aggregation (self‐sorting) or synergistic aggregation (coassembly). Herein, a unique manipulation of self‐sorting/coassembly aggregation and the observation of switchable stimulus‐responsiveness transfer in a two component self‐assembly system are reported. Two building blocks bearing the same cholesterol group give versatile topological structures in polar and nonpolar solvents. One building block (cholesterol conjugated cynanostilbene, CCS) consists of cholesterol conjugated with a cynanostilbene unit, and the other one (C10CN) is comprised of cholesterol connected with a naphthalimide group having a flexible long alkyl chain. Their assemblies including gel, crystalline plates, and vesicles are obtained. In gel and crystalline plate phases, the self‐sorting behavior dominates, while synergistic coassembly occurs in vesicle phase. Since CCS having the cyanostilbene group can respond to the light irradiation, it undergoes light‐induced chiral amplification. C10CN is thermally responsive, whereby its supramolecular chirality is inversed upon heating. In coassembled vesicles, it is interestingly observed that their responsiveness can be transferred by each other, i.e., the C10CN segment is sensitive to the light irradiation, while CCS is thermoresponsive. This unprecedented behavior of the property transfer may shine a light to the precise fabrication of smart materials.

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“…They can be studied in real time at the micro-to nanomolar concentration ranges using fluorescence resonance energy transfer (FRET) (23). We recently reported the synthesis of labeled versions of resorcinarenes and cavitand monomers (24,25). Perylene labeled resorcinarene 1 A (acceptor fluorophore) was added to pyrene labeled cavitand 2 D (donor fluorophore) in mesitylene with both components at 250 nM.…”

Section: Resultsmentioning

confidence: 99%

Disproportionation and self-sorting in molecular encapsulation

Ajami

Hou

Dale

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

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Self-assembled capsules are nanoscale structures made up of multiple synthetic subunits held together by weak intermolecular forces. They act as host structures that can completely surround small molecule guests of the appropriate size, shape and chemical surface. Like their biological counterparts, multimeric enzymes and receptors, the subunits of the capsules are generally identical, and lead to homomeric assemblies of high symmetry. In both biological and synthetic systems small variations in structures are tolerated and lead to heteromeric assemblies with slightly different recognition properties. The synthetic capsules are dynamic, with lifetimes from milliseconds to hours, and allow the direct spectroscopic observation of smaller molecules inside, under ambient conditions at equilibrium in solution. We report here the assembly of hybrid capsules made up of 2 very different structures, both capable of forming their own homomeric capsules through hydrogen bonding. These hybrids exhibit host properties that differ markedly from the parent capsules, and suggest that other capsules may emerge from seemingly unrelated modules that have curved surfaces and are rich in hydrogen bonding capabilities. R eversible encapsulation complexes are supramolecular structures in which guest molecules are completely surrounded by a self-assembled host structure (1). The complexes provide access to isolated species that cannot be seen in bulk solution (2); they act as nanometric reaction chambers (3), as means to stabilize reagents (4,5), and as spaces where new forms of stereochemistry can emerge (6). The forces holding the assembly together can be hydrophobic effects (7), salt bridges (8), metal/ligand interactions (9,10), and hydrogen bonds. The capsules form when, and only when, suitable guests are present to fill the space inside. For example, 6 molecules of resorcinarene 1 (Fig. 1) and 8 molecules of water form a hexameric capsule 1 6 in the solid state through a seam of 60 hydrogen bonds (11). The capsule also self-assembles in solution with wet solvents such as chloroform and benzene inside (12,13) or in the presence of large quaternary ammonium guests (14,15). The resorcinarene can be elaborated to the cavitand 2, which dimerizes in chloroform to capsule 2 2 through a seam of 8 bifurcated hydrogen bonds. When dissolved in chloroform, the capsule forms around 3 solvent molecules. Alternatively, a hybrid structure 1.2 forms immediately on mixing the 2 homomeric capsules 1 6 and 2 2 and all 3 capsule assemblies coexist in the same solution (16). The exchange of partners was surprising, because ''self-assembly'' implies a distinction between self and nonself, with some selection, correction and sorting at work (17,18), but these capsules are related because they share resorcinarene modules that fix their dimensions and symmetries. Here, we report a new example of hybrid formation from 2 unrelated capsules. ResultsThe capsule 3 2 is a notional ''tennis ball'' (19) that self-assembles through hydrogen bonding around small mo...

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Assembly and Exchange of Resorcinarene Capsules Monitored by Fluorescence Resonance Energy Transfer

Cited by 116 publications

References 19 publications

Metallo-supramolecular capsules

Metallo-supramolecular capsules

Environment‐Adaptive Coassembly/Self‐Sorting and Stimulus‐Responsiveness Transfer Based on Cholesterol Building Blocks

Disproportionation and self-sorting in molecular encapsulation

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