Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

Aydogan, Abdullah; Coady, Daniel J.; Kim, Sung Kuk; Akar, Ahmet; Bielawski, Christopher W.; Márquez, Manuel; Sessler, Jonathan L.

doi:10.1002/ange.200803970

Cited by 32 publications

(20 citation statements)

References 27 publications

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“…It should be possible to improve the sensing performance by producing next generation squaraine rotaxanes with increased Cl À affinity and selectivity, [10,11] increased amount of fluorescence quenching relief upon binding, and optimized dipsticks that can detect the presence of hydrophilic salts like Na + Cl À . [26,27] Experimental Section…”

Section: Resultsmentioning

confidence: 99%

Squaraine Rotaxane as a Reversible Optical Chloride Sensor

Gassensmith

Matthys

Lee

et al. 2010

Chemistry A European J

142

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A mechanically interlocked squaraine rotaxane is comprised of a deep-red fluorescent squaraine dye inside a tetralactam macrocycle. NMR studies show that Cl(-) binding to the rotaxane induces macrocycle translocation away from the central squaraine station, a process that is completely reversed when the Cl(-) is removed from the solution. Steady-state fluorescence and excited-state lifetime measurements show that this reversible machine-like motion modulates several technically useful optical properties, including a three-fold increase in deep-red fluorescence emission that is observable to the naked eye. The excited states were characterized quantitatively by time-correlated single photon counting, femtosecond transient absorption spectroscopy, and nanosecond laser flash photolysis. Cl(-) binding to the rotaxane increases the squaraine excited singlet state lifetime from 1.5 to 3.1 ns, and decreases the excited triplet state lifetime from >200 to 44 micros. Apparently, the surrounding macrocycle quenches the excited singlet state of the encapsulated squaraine dye and stabilizes the excited triplet state. Prototype dipsticks were prepared by adsorbing the lipophilic rotaxane onto the ends of narrow, C18-coated, reverse-phase silica gel plates. The fluorescence intensity of a dipstick increased eighteen-fold upon dipping in an aqueous solution of tetrabutylammonium chloride (300 mM) and was subsequently reversed by washing with pure water. It is possible to develop the dipsticks for colorimetric determination of Cl(-) levels by the naked eye. After dipping into aqueous tetrabutylammonium chloride, a dipstick's color slowly fades at a rate that depends on the amount of Cl(-) in the aqueous solution. The fading process is due primarily to hydrolytic bleaching of the squaraine chromophore within the rotaxane. That is, association of Cl(-) to immobilized rotaxane induces macrocycle translocation and exposure of the electrophilic C(4)O(2) core of the squaraine station, which is in turn attacked by the ambient moisture to produce a bleached product.

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Section: Resultsmentioning

confidence: 99%

Squaraine Rotaxane as a Reversible Optical Chloride Sensor

Gassensmith

Matthys

Lee

et al. 2010

Chemistry A European J

142

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“…Noch neuer ist die Entwicklung von Salicylaldoxim-basierten Rezeptoren zur Extraktion von Ionenpaaren des Typs MX 2 . [32] Aus dieser Forschung kçnnten bedeutende Anwendungen in der Medizin hervorgehen, z. Sessler und Mitarbeiter beschrieben die Fähigkeit von gemischten Methacrylsäuremethylester-Copolymeren mit anhängenden Calix [4]pyrrol-und Benzo- [15]krone-5-Untereinheiten zur Extraktion von Kaliumhalogenidsalzen aus wässrigen Medien.…”

Section: Rezeptorenunclassified

“…Sessler und Mitarbeiter beschrieben die Fähigkeit von gemischten Methacrylsäuremethylester-Copolymeren mit anhängenden Calix [4]pyrrol-und Benzo- [15]krone-5-Untereinheiten zur Extraktion von Kaliumhalogenidsalzen aus wässrigen Medien. [32] Aus dieser Forschung kçnnten bedeutende Anwendungen in der Medizin hervorgehen, z. B. zur Kontrolle von Hyperkaliämie.…”

Section: Agentien Zur Salzextraktionunclassified

Heteroditope Rezeptoren zur Ionenpaarerkennung

McConnell

Beer

2012

Angewandte Chemie

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Bei der Ionenpaarerkennung handelt es sich um ein junges Forschungsgebiet, das aus der Anionen‐ und Kationen‐Koordinationschemie hervorgegangen ist. Spezielle Designtypen heteroditoper Ionenpaarrezeptoren sowie die Komplexität der Ionenpaarbindung werden zur Illustration der Schlüsselkonzepte, z. B. der Kooperativität, beschrieben. Die Bedeutung dieses Forschungsgebiets wird durch eine Vielzahl möglicher Anwendungen von Ionenpaarrezeptoren widergespiegelt, einschließlich der Anwendung als Membrantransporter, als Agentien zur Solubilisierung von Salzen und als Sensoren.

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“…Thus, it is very meaningful to exploit new strategies to design fluorescent probes for sensing F  with high selectivity. And some excellent F  receptors and probes have been reported [18][19][20][21]. Due to the Lewis acidity of boron center, triarylboranes with bulky aryl substitutes can react with small nucleophilic anions including F  to afford fluoroborate anions.…”

Section: Introductionmentioning

confidence: 99%

A near-infrared phosphorescent probe for F− based on a cationic iridium(III) complex with triarylboron moieties

Liu

Zhao

et al. 2011

Sci. China Chem.

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In this work, a near-infrared (NIR) phosphorescent probe for F  based on a cationic Ir(III) complex [Ir(Bpq) 2 (quqo)]PF 6 (1) with dimesitylboryl (Mes 2 B) groups on the cyclometalated C^N ligands (Bpq) and 2-(quinolin-2-yl)quinoxaline (quqo) as N^N ligand was designed and synthesized. The excited state properties of 1 were investigated in detail using molecular orbital calculations and experimental methods. Upon excitation, complex 1 shows NIR phosphorescent emission around 680 nm. Interestingly, the complex can be excited with long wavelength around 610 nm. Such long-wavelength excitation can reduce the background emission interference and improve the signal-to-noise ratio. Furthermore, the selective binding between boron atom and F  can give rise to the quenching of emission and realize the near-infrared phosphorescent sensing for F  . We wish that the results reported herein will be helpful for the further design of excellent near-infrared phosphorescent probes based on heavy-metal complexes.

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Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides

Cited by 32 publications

References 27 publications

Squaraine Rotaxane as a Reversible Optical Chloride Sensor

Squaraine Rotaxane as a Reversible Optical Chloride Sensor

Heteroditope Rezeptoren zur Ionenpaarerkennung

A near-infrared phosphorescent probe for F− based on a cationic iridium(III) complex with triarylboron moieties

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