Selective d-glucosamine hydrochloride fluorescence signalling based on ammonium cation and diol recognition

Cooper, Christopher R.; James, Tony D.

doi:10.1039/a703300a

Cited by 84 publications

(49 citation statements)

References 14 publications

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“…8 Anthracene has also been incorporated as the fluorescent element for sensing Cu 2+ ions 9 and d-glucosamine. 10 Very recently, Kubo, Ishige and Sakurai have prepared and studied N,NA-bis(9-anthrylmethyl)-4,13-diaza-18-crown-6 1 for use as a fluorescent cation sensor. In the latter case, some cation binding selectivity and cation-induced fluorescence change were observed, but the results were generally modest.…”

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confidence: 99%

Intramolecular C–H‥O hydrogen bonding reduces cation complexation strength in a fluorescent crown ether

Wall¹,

Meadows²,

Barbour³

et al. 1999

Chem. Commun.

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Complexes of the fluorescent crown ether, N,N-bis(9-anthrylmethyl)-4,13-diaza-18-crown-6, with NaI 3 and KSCN reveal the presence of intramolecular C-H…O hydrogen bonds that appear to control conformation and lead to reduced cation binding affinity.For more than a decade, the fluorescent properties of macrocycles have proved fascinating. 1 A hope has been that fluorescent residues appended to macrocycles would afford lariat ethers 2 that could function as cation sensors. 3 Indeed, de Silva and de Silva demonstrated 'fluorescent signaling' in N-(9-anthrylmethyl)aza-15-crown-5 and -18-crown-6 nearly 15 years ago. 4 Anthracene has proved particularly popular as the fluorescent element. It has, for example, been incorporated into crowns and cryptands used as probes of phospholipid membrane fluidity. 5 It has been attached to one crown, to two crowns, and via the 9-and 10-positions of a single molecule to a macrocycle to afford proton sensors. 6 Two anthracenes incorporated into a macrocycle 7 and two anthracenes attached to a crown afforded a crown-cryptand photoswitch. 8 Anthracene has also been incorporated as the fluorescent element for sensing Cu 2+ ions 9 and d-glucosamine. 10 Very recently, Kubo, Ishige and Sakurai have prepared and studied N,NA-bis(9-anthrylmethyl)-4,13-diaza-18-crown-6 1 for use as a fluorescent cation sensor. In the latter case, some cation binding selectivity and cation-induced fluorescence change were observed, but the results were generally modest. This is surprising for such a widely used and strongly fluorescent residue. We now report the first solid state structures of 1 bound by either Na + or K + . Intimate C-H…O hydrogen bonding between the sidearm and macrorings clearly decrease the ability of 1 to form stable cation complexes and, in turn, diminish their utility as sensors.Compound 1 was prepared by heating commercial 9-chloromethylanthracene, 4,13-diaza-18-crown-6, 11 and Na 2 CO 3 in MeCN for 72 h. Crystallization from toluene afforded 1 as yellow needles (68%, mp 195-196 °C). 12 Kubo and co-workers report 1 in 90% yield as yellow needles (from CHCl 3 ) having mp 189-190 °C. The NaI 3 complex of 1 was isolated from a mixture of 1 and NaI (1+1) in THF that was not protected from the air. The rhombohedral crystals obtained (dark yellow to brown) had the stoichiometry 1·NaI 3 ·(THF) 2 and decomposed on melting, presumably with loss of THF, at ca. 215 °C. A projection of the complex is shown in Fig. 1.There are several notable features about this complex. First, the macroring is in the D 3d conformation, as expected. The average Na + -O distance is 2.46 Å and the Na + -N distances are 3.03 and 2.92 Å. These values are typical for diaza-18-crown-6 Na + complexes. The sidearms are in the anti conformation, one being above, and the other below, the mean plane of the macroring heteroatoms. The anti orientation of the anthryl sidearms effectively excludes the anion from the cation's solvation sphere. It is especially interesting that the two (disordered) THF molecules (normally excellent...

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mentioning

confidence: 99%

Intramolecular C–H‥O hydrogen bonding reduces cation complexation strength in a fluorescent crown ether

Wall¹,

Meadows²,

Barbour³

et al. 1999

Chem. Commun.

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“…Intermediate 1 reacts with KI/LiBr to generate 10-methanol-9-anthracene carboxyaldehyde (2). 14 The next reaction involves the coupling of 2 to the resins Merrifield, Argopore-Cl, Argogel-Cl and Wang-Cl through a nucleophilic displacement of chloride in the presence of THF/NaH to yield the resins-10-oxymethyl-anthracene-9-carbaldehyde (3a-d). Then, 3 is reduced with NaBH 4 to produce PS-10-oxymethyl-anthracen-9-yl)-methanol (4a-d).…”

Section: Resultsmentioning

confidence: 99%

Combinatorial synthesis of fluorescent trialkylphosphine sulfides as sensor materials for metal ions of environmental concern

Castillo¹,

Rivero²

2004

Arkivoc

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A combinatorial library of diverse alkyl-phosphine sulfides bound to Merrifield, Argopore, Argogel and Wang resins was synthesized and evaluated for their sensing properties. The library consists of 12 products with the anthranyl group as a fluorophore and phosphine sulfide alkyl derivatives as receptors of transition and heavy metal ions. The fluorescence spectral characteristics and the properties as sensing phase of these materials towards Pb(II) and Cu(II) were established.

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“…For instance, sugar binding to aminomethylphenylboronic acid to produce boronate ester leads to a stronger B-N bond which stops the PET process. Then 34 [85,86] with the two receptors at the appropriate distance of separation could target glucosamine. In this case, the pH value needs to be chosen so that glucosamine is protonated but not the nitrogen centre in the azacrown ether.…”

Section: Connected Inputsmentioning

confidence: 99%

Molecular Logic Gates and Luminescent Sensors Based on Photoinduced Electron Transfer

Silva

Uchiyama

2010

Luminescence Applied in Sensor Science

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The competition between Photoinduced electron transfer (PET) and other de-excitation pathways such as fluorescence and phosphorescence can be controlled within designed molecular structures. Depending on the particular design, the resulting optical output is thus a function of various inputs such as ion concentration and excitation light dose. Once digitized into binary code, these input-output patterns can be interpreted according to Boolean logic. The single-input logic types of YES and NOT cover simple sensors and the double- (or higher-) input logic types represent other gates such as AND and OR. The logic-based arithmetic processors such as half-adders and half-subtractors are also featured. Naturally, a principal application of the more complex gates is in multi-sensing contexts.

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Selective d-glucosamine hydrochloride fluorescence signalling based on ammonium cation and diol recognition

Cited by 84 publications

References 14 publications

Intramolecular C–H‥O hydrogen bonding reduces cation complexation strength in a fluorescent crown ether

Intramolecular C–H‥O hydrogen bonding reduces cation complexation strength in a fluorescent crown ether

Combinatorial synthesis of fluorescent trialkylphosphine sulfides as sensor materials for metal ions of environmental concern

Molecular Logic Gates and Luminescent Sensors Based on Photoinduced Electron Transfer

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