Synthesis, Binding and Fluorescence Studies of Bis-2-amidopyrrole Receptors for Bis-carboxylate Anions

Jiménez, Belén; Calle, Emilio; Caballero, C.

doi:10.3390/s90301534

Cited by 9 publications

(4 citation statements)

References 18 publications

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“…12,13 The amide variant H 6 L 2 was prepared in two high-yielding steps from the tripyrrole that involved the formation of the 2-trichloroacyl derivative and its subsequent nucleophilic substitution reactions with either cyclohexylamine or methylamine. 14 The 1 H NMR spectrum of H 6 L 2a (R′ = Cy) in CDCl 3 has characteristic pyrrole and amide N-H resonances at 10.9 and 7.78 ppm, respectively, the latter a doublet due to coupling to the methine hydrogen of the cyclohexyl substituent.…”

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Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands

2012

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Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands Citation for published version:Hart, JS, Nichol, GS & Love, JB 2012, 'Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands ' Dalton Transactions, vol. 41, no. 19, General rightsCopyright for the publications made accessible via the Edinburgh Research Explorer is retained by the author(s) and / or other copyright owners and it is a condition of accessing these publications that users recognise and abide by the legal requirements associated with these rights. Take down policyThe University of Edinburgh has made every reasonable effort to ensure that Edinburgh Research Explorer content complies with UK legislation. If you believe that the public display of this file breaches copyright please contact openaccess@ed.ac.uk providing details, and we will remove access to the work immediately and investigate your claim.

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“…12,13 The amide variant H 6 L 2 was prepared in two highyielding steps from the tripyrrole that involved the formation of the 2-trichloroacyl derivative and its subsequent nucleophilic substitution reactions with either cyclohexylamine or methylamine. 14 The 1 H…”

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confidence: 99%

Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands

2012

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“…The diamine derivative of title compound has been used on supramolecular chemistry as afluorescente spacer in pyrrole receptors for the recognition and sensing of bis-carboxylate anions [1]. The crystal contains an unique molecule and am olecule of the solvent in the asymmetric unit.…”

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Crystal structure of dimethyl 5-(acridin-9-yloxy)isophthalate - methanol (1:1), C₂₃H₁₇NO₅ · CH₃OH

Jimenez¹,

Gonzalez²,

Caballero³

2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound has been synthesized from 9-chloroacridine and the commercially available dimethyl 5-hydroxyisophthalate by aW illiamson reaction. To as olution of NaOH (375 .mg, 9.4 .mmol) in t-BuOH (40 mL), dimethyl 5-hydroxy-isophthalate (1.5 g, 7mmol) in DMSO (30 mL) was added and stirred under argon atmosphere for 30 minutes. 9-Chloroacridine (1.25 . g, 5.8 .mmol) in DMSO (25 mL) was then added and the mixture was heated under reflux for 1.5 h. The solid obtained by precipitation after ice addition was solved in CHCl 3 and worked-up as usual to yield the title compound (1.5 g, 83 %), which was recrystallized from ethyl acetylacetate/methanol (1:1, v/v). Experimental detailsThe hydrogen atoms were positioned geometrically, with C-H distances constrained to 0.93 Å (aromatic) and 0.96 Å (methyl), and refined in riding mode with U iso(H) = xUeq(C), where x =1.5 for methyl Hatoms and x =1.2 for all other Hatoms, respectively. The hydroxyl hydrogen atom was refined with adistance restraint of 0.82 Å,starting from the difference Fourier map coordinates and with U iso(H) =1.5 Ueq(O). DiscussionThe title molecule, dimethyl 5-(acridin-9-yloxy)isophthalate, is a fluorescent molecule with astructure based on adimethyl benzene-1,3-bis-carboxylate (dimethyl isophthalate) framework and aphenolic function at C5 position derivatized as an acridine ether group. The diamine derivative of title compound has been used on supramolecular chemistry as afluorescente spacer in pyrrole receptors for the recognition and sensing of bis-carboxylate anionsThe crystal contains an unique molecule and am olecule of the solvent in the asymmetric unit. All the bond lengths and angles are within the normal ranges. The title molecule consists of abenzene ring with two methyl esters and one acridine ring as susbtituents. The planar conformation of the ester groups is established from the torsion angles O5-C22-O4-C18 (178.8(2)°)and O2-C20-O3-C16 (179.0(2)º). In the molecule, the acridine group is almost perpendicular to the aromatic ring with the torsion angle C14-O1-C10-C9 of 89.3(6)º. As trong intermolecular interaction between the hydroxyl of the solvent molecule and nitrogen atom of the acridine group is seen.

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“…Organic carboxylic acids are one kind of basic building block for many natural products, biological molecules and drugs, and searching for their effective molecular sensors has been an active topic in the last few decades. Many sensor molecules have been created for aromatic and short-chain (mono-or di-) carboxylic acids or their anions, [25][26][27][28][29][30][31][32][33][34][35] and two papers concerning the selective uorescent discrimination of long-chain (fatty) carboxylates in water have also been reported. 20,21 However, to date, no sensor has yet been reported for medium-chain fatty acids.…”

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confidence: 99%

The first fluorescent sensor for medium-chain fatty acids in water: design, synthesis and sensing properties of an organic–inorganic hybrid material

Gong

Sun

et al. 2013

J. Mater. Chem. B

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This paper reports the first fluorescent sensor for medium-chain fatty acids in water. The hybrid sensing material (S2) was prepared by the reaction of a rationally designed "recognition center", N-butyl-4piperazin-1,8-naphthalimide, with a 3-glycidoxypropyl group which is pre-grafted on the interior of a mesoporous solid (MCM-41). The organo-functionalization of the mesoporous solid (MCM-41) was confirmed by FT-IR, 29 Si MAS NMR and elemental analysis. The results of XRD, N 2 physical adsorptiondesorption, SEM and TEM studies proved that the organized structure of the nanoscopic porous solid is preserved after the reactions. The fatty acid-selective signaling behavior of S2 was investigated in water at pH ¼ 5.80/7.16/8.00. This material displays much stronger fluorescence enhancement with C 8 -C 12 fatty acids than with the shorter and longer chains in aqueous media, both in the absence and in the presence of aromatic acids.

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Synthesis, Binding and Fluorescence Studies of Bis-2-amidopyrrole Receptors for Bis-carboxylate Anions

Cited by 9 publications

References 18 publications

Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands

Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands

Crystal structure of dimethyl 5-(acridin-9-yloxy)isophthalate - methanol (1:1), C₂₃H₁₇NO₅ · CH₃OH

The first fluorescent sensor for medium-chain fatty acids in water: design, synthesis and sensing properties of an organic–inorganic hybrid material

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Synthesis, Binding and Fluorescence Studies of Bis-2-amidopyrrole Receptors for Bis-carboxylate Anions

Cited by 9 publications

References 18 publications

Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands

Directed secondary interactions in transition metal complexes of tripodal pyrrole imine and amide ligands

Crystal structure of dimethyl 5-(acridin-9-yloxy)isophthalate - methanol (1:1), C23H17NO5 · CH3OH

The first fluorescent sensor for medium-chain fatty acids in water: design, synthesis and sensing properties of an organic–inorganic hybrid material

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Crystal structure of dimethyl 5-(acridin-9-yloxy)isophthalate - methanol (1:1), C₂₃H₁₇NO₅ · CH₃OH