A Hydrophobic Nanocapsule Controls the Photophysics of Aromatic Molecules by Suppressing Their Favored Solution Pathways

Kaanumalle, Lakshmi S.; Gibb, Corinne L. D.; Gibb, Bruce C.; Ramamurthy, V.

doi:10.1021/ja0425381

Cited by 225 publications

(177 citation statements)

References 24 publications

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“…18 reported exceptions to the 55 AE 0.9% rule in rare cases with a maximum of 75%, while Bruce et al 19 observed a higher packing efficiency of 82% with deep cavity cavitands. The (2 Â 1,4-dioxane$2 Â H 2 O) 2 @(4(OTf) 4 ) 2 capsule thus represents one of the most dense dimeric capsules.…”

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confidence: 97%

Dimeric resorcinarene salt capsules with very tight encapsulation of anions and guest molecules

Pan

Beyeh

2015

RSC Adv.

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Crystallization of N-cyclohexyl ammonium resorcinarene triflate from methanol results in a dimeric capsule capable of trapping two triflate anions and two methanol molecules within a 341Å 3 cavity while with 1,4-dioxane as a guest it forms a new larger dimeric capsule with volume of 679Å 3 encapsulating four 1,4-dioxane and four water molecules, resulting in packing coefficients of 0.75 and 0.67, respectively.The concerted utilization of multiple weak interactions such as electrostatic forces, hydrogen bonding, cation/p, -CH/p and p/p interactions in the design of functional assemblies, is a growing area of contemporary supramolecular chemistry with potential applications in biology and materials chemistry. 1Resorcinarenes are an important class of receptor compounds and/or building blocks in supramolecular chemistry.2 In their C 4v conformation, intramolecular hydrogen bonds between adjacent phenolic hydroxyl groups help maintain the bowl shape cavity suitable for guest binding.2 These macrocyclic host compounds manifest a multitude of molecular recognition events, resulting in host-guest assemblies such as 1 : 1 inclusion complexes, 3 dimeric or hexameric capsular 4 assemblies and nano-tubular 5 structures in the presence of specic guest compounds under suitable conditions.Anions have a major role in biological processes. 6 Examples of anions or anionic compounds in biology include many enzyme substrates and cofactors.6 Anions are generally larger than their isoelectronic cations with wider solvation properties and are more sensitive to pH with a larger range of geometric/ structural modulations. 6These characteristics make the binding/recognition of anions more challenging when compared to cation binding.6 However, anion binding receptors and their applications as sensors, or their use in ions channels is widely reported.7 Anions can also be used to template the formation of ionic and metal coordination cages as well as interlocked systems.8 The propensity of anions to form hydrogen bonds and be involved in electrostatic interactions implies, incorporating these characteristics in the design of molecular receptors, could lead to very efficient anion receptors. 9The N-alkyl ammonium resorcinarene halides, NARXs, are obtained by cleaving the corresponding tetrabenzoxazines 10 with mineral acids (usually HCl and HBr) under reuxing conditions.11 The concave cavity of the resorcinarenes is maintained in these large organic halide salts through a strong circular intramolecular hydrogen bonded cation-anion (/NR 2 H 2 + /X À /) 4 seam between the ammonium groups and the halides anions.11 These halide salts have been shown to be excellent halogen bond acceptors and manifest themselves as deep cavity cavitands 12 and halogen bonded capsules. 13 We have recently investigated the binding modes with non-halide anions: picrate (aromatic planar), nitrate (trigonal planar) and triate (ellipsoidal).14 While the picrate salt was synthesized from the corresponding cleavage of the tetrabenzoxazine with picric acid, the nitrat...

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confidence: 97%

Dimeric resorcinarene salt capsules with very tight encapsulation of anions and guest molecules

Pan

Beyeh

2015

RSC Adv.

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“…Selbstassemblierte molekulare Kapseln werden durch kovalente Bindungen gebildet [1] oder reversibel durch Wasserstoffbrücken, [2][3][4][5][6][7][8] Wechselwirkungen zwischen einem Metall und seinen Liganden [9,10] oder hydrophobe Effekte zusammengehalten. [11] Gäste liegen in Kapseln typischerweise in molaren Konzentrationen vor. Bei Anwesenheit von zwei oder mehreren Gästen besteht eine hohe Wahrscheinlichkeit dafür, dass diese miteinander wechselwirken und molekulare Anordnungen entstehen, die einer supermolekularen Chemie zweiter Ordnung [12] entsprechen ("Komplexe innerhalb von Komplexen"), oder miteinander reagieren [9b] und dabei sogar Reaktionswegen folgen, die in Lösung unwahrscheinlich sind.…”

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Eingekapselte Carbonsäure‐Dimere mit verkürzten Wasserstoffbrücken

et al. 2010

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“…The emission peak at 515 nm is ascribed to the anthracene excimer emission, which is generally observed in the highly concentrated anthracene solution and film [27]. The excimer emission of the PMAn-Temp was stronger than that of PMAn synthesized from …”

Section: Optical Properties Of Synthesized Pmanmentioning

confidence: 92%

Template assisted polymerization of functional materials and their opto-electronic properties

et al. 2011

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Highly ordered iron incorporated mesoporous silica (Fe-SBA15) was prepared and used as a template for catalytic polymerization of functional molecules. The mesoporous catalysts were used as an oxidative nano-reactor in heterogeneous catalytic reactions to afford highly fluorescent poly(methylene anthracene)s (PMAn) when anthracene was used as a monomer. The structure of the mesoporous Fe-SBA15 was 2D channel with large surface area of 710 m 2 /g and pore size of 9.2 nm. The fluorescent polymer was synthesized with high yield of 90 % in short reaction time. The synthesized polymer PMAn showed good emission properties with high excimer emission, which was highly affected by the pore size of the reactor. This indicated that the optical properties of fluorescent polymers synthesized from this method could be controlled by the pore size of the mesoporous templates.

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A Hydrophobic Nanocapsule Controls the Photophysics of Aromatic Molecules by Suppressing Their Favored Solution Pathways

Cited by 225 publications

References 24 publications

Dimeric resorcinarene salt capsules with very tight encapsulation of anions and guest molecules

Dimeric resorcinarene salt capsules with very tight encapsulation of anions and guest molecules

Eingekapselte Carbonsäure‐Dimere mit verkürzten Wasserstoffbrücken

Template assisted polymerization of functional materials and their opto-electronic properties

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