Molecular Switch Triggered by Solvent Polarity: Synthesis, Acid–Base Behavior, Alkali Metal Ion Complexation, and Crystal Structure

Ambrosi, Gianluca; Dapporto, P.; Formica, Mauro; Fusi, Vieri; Giorgi, Luca; Guerri, Annalisa; Micheloni, Mauro; Paoli, Paola; Pontellini, Roberto; Rossi, Patrizia

doi:10.1002/chem.200390090

Cited by 28 publications

(32 citation statements)

References 63 publications

(16 reference statements)

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“…[HL]ClÁ8H 2 O: the asymmetric unit of [HL]ClÁ8H 2 O contains a molecule of the monocharged ligand, a chloride ion and eight water molecules. The conformation of the [12]aneN 4 ring can be described by the sequence of its dihedral angles as [2424] C corners, 31 thus resulting that the nitrogen atoms N(3) and N( 5) are closer to each other than are the N(2) and N(4) atoms (2.785(4) A ˚vs. 5.427 (4) A ˚) (Fig.…”

Section: Description Of the Structurementioning

confidence: 99%

“…[9][10][11] The attached moieties can also be driven to cooperate by the macrocyclic skeleton, thus forming new binding sites inside the molecule having different hard-soft capabilities. 12 3-Hydroxy-2(1H)-pyridinone and its derivative molecules are chelating agents that have shown particular binding and sequestering properties towards highly charged metal cations. 13 For example, they can produce decorporation of heavy metals in animals, 14 showing high affinity towards iron(III).…”

Section: Introductionmentioning

confidence: 99%

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New ligand bearing preorganized binding side-arms interacting with ammonium cations: Synthesis, conformational studies and crystal structureElectronic supplementary information (ESI) available: molecular modeling studies. See http://www.rsc.org/suppdata/nj/b3/b306778e/

et al. 2003

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The synthesis and characterization of the new tetraazamacrocycle 4-(N),10-(N)-bis[2-(3-hydroxy-2-oxo-2Hpyridin-1-yl)acetamido]-1,7-dimethyl-1,4,7,10-tetraazacyclododecane (L) is reported. L shows two 3-(hydroxy)-1-(carbonylmethylen)-2(1H)-pyridinone moieties as side-arms of a tetra-aza-macrocyclic base. The key coupling of side-arms was studied and the most significant results were obtained by activating the 3-(benzyloxy)-1-(carboxymethyl)-2(1H)-pyridinone as pentafluorophenol ester. The acid-base properties of L and its capability to interact with simple ammonium cations were investigated by potentiometric measurements in aqueous solution (298.1 AE 0.1 K, I ¼ 0.15 mol dm À3 ). Protonated species of L can bind NH 4 + or primary ammonium cations such as MeNH 3 + discriminating them from secondary or tertiary ammonium cations such as Me 2 NH 2 + or Me 3 NH + which are not bound in aqueous solution.1 H and 13 C NMR spectra showed the existence in solution of two conformers on the NMR time scale due to the rotational restriction of the two N-C=O groups. The activation parameters were determined by dynamic variable-temperature NMR analysis.Molecular dynamics calculations gave results in agreement with the experimental data for both conformation and ammonium-binding studies, underlining that the transformation of the two secondary amines of the macrocyclic base to amide functions, forces the side-arms to remain fixed in position, almost face to face and thus to be preorganized to interact with other species. The crystal structure of the [HL]ClÁ8H 2 O species shows the high number of preorganized hydrogen bond sites capable, in this case, of interacting directly with five H 2 O molecules.

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Section: Description Of the Structurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New ligand bearing preorganized binding side-arms interacting with ammonium cations: Synthesis, conformational studies and crystal structureElectronic supplementary information (ESI) available: molecular modeling studies. See http://www.rsc.org/suppdata/nj/b3/b306778e/

et al. 2003

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“…Six-coordinatedsodium(I)environments are present in the most of the comparativelyf ew sodium(I)c omplexes, such as in 1,7-bis(2,2¢ -dihydroxybiphen-3-yl)-4,10-dimethyl-1,4,7,10-tetraazacyclododecane)sodium acetonitrile solvate [1], tetrakis(acetonitrile) bis(tetrahydrofuran)sodium bis(2,6-bis-benzimidazol-2-yl)pyridine)iron [2] and bis(2-(4¢ -thiazolyl)benzimidazole-N , N ¢ ) bis(octadeuterofuran)sodium [3]. Inthe course of studies of phenanthroline complexes, we have synthesized the title mononuclear …”

Section: Discussionmentioning

confidence: 99%

Crystal structure of diaquabis(1,10-phenanthroline-k2N, N')sodium chloride, [Na(H2O)2(C12H8N2)2]Cl

B.-S.¹

2006

Zeitschrift Für Kristallographie - New Crystal Structures

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C 24H 20ClN 4 NaO 2 ,monoclinic, P 121 / c 1(no. 14), a =16.352(3) Å, b =15.579(3) Å, c =9.132(2) Å, b =104.54(3)°, V =2251.8 Å 3 , Z =4, R gt (F) =0.056, wRref(F 2 ) =0.161, T =293 K. Source of materialThe title compound was obtainedserendipitously from the reaction of manganic dichloride dihydrate (0.40 g, 2.47 mmol), 1,10-phenanthroline monohydrate (0.13 g, 0.66 mmol), phthalic acid (0.43 g, 2.59 mmol) in water (10 mL), and then the pHwas raised to about 8.5 with 1.0 Msolutionofsodium carbonate. The mixture was stirred for ca. 4h.Subsequently, the resultingsuspension was heated in a2 5m lTeflon-lined stainless steel autoclavea t 453 Kfor 5days. After the autoclave was cooled to room temperature, the solid was filtered off. The resulting yellow filtrate was allowed to stand at room temperature and slow evaporation for two years afforded yellowish block-shapedcrystals. DiscussionSix-coordinatedsodium(I)environments are present in the most of the comparativelyf ew sodium(I)c omplexes, such as in 1,7-bis(2,2¢ -dihydroxybiphen-3-yl)-4,10-dimethyl-1,4,7,10-tetraazacyclododecane)sodium acetonitrile solvate figure, top). The Na-Nbond distances are in the range of 2.460(2) Åto 2.563(2) Å.The Na-O2and Na-O1bond lengths are 2.358(2) Åand 2.401(2) Å,r espectively. The monovalent [Na(H 2 O) 2 (phen) 2 ] + complex cations are interlinked via hydrogen bonds between the Cl -anions and Oatoms of the coordinated water molecules. The chelating phen ligands exhibit nearly perfect co-planarity, each phen ligand is sandwiched by two phen ligands from two neighboring mononuclear complex cations. The mean interplanar distances are 3.469 Åand 3.566 Å,a lternatively, indicating p -p stacking interactions along [010] direction (figure, bottom). Moreover, there are weak hydrogen bonds between Cl -anions and o -phenanthroline H3atoms ( d (C3···Cl1) = 3.706 Å, Ð C3-H3···Cl1 =146.5°). Through the hydrogen bonds and p -p stacking interactions, athree-dimensional supramolecular network is constructed.

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“…Molecular switches are the simplest expression of molecular machines. They are modulated by various stimuli, including light irradiation, electrochemistry reaction, variations of pH, heat, solvent polarity, cation or anion binding, allosteric effect, temperature change, and reversible covalent bond formation, and so on. We focus on the external electric field stimulus due to interesting electric field effects on molecular properties …”

Section: Introductionmentioning

confidence: 99%

Small Janus dimer as electric field manipulated molecular clam switch and electric information storage unit

Chen

Liu

et al. 2019

Int J of Quantum Chemistry

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A small Janus molecular dimer, as external electric field (Fz) manipulated both a molecular clam switch and a novel electric information storage unit, is found by quantum chemical computations for the first time. The molecular clam switching is intriguing and reversible. A critical Fz value of 95 × 10−4 au causes a dramatically open change in conformation from Closed form to Open form. And a small reversed electric field of Fz = −10 × 10−4 au performs a close change from Open form to Closed form. In the switching process, owing to the existence of a great electric dipole moment (μ) contrast between 0 and 22.13 D, the molecular clam switch may serve as an electric information storage unit. Gratifyingly, the reading, writing, and erasing of binary information on the electric information storage unit are easy. And further calculations show that Janus graphene fragment dimer can also serve as a molecular clam switch. Thus, this work proposes a new molecular switch prototype in the invention of artificial molecular machines, and a novel electric information storage unit in the field of molecular electronics.

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Molecular Switch Triggered by Solvent Polarity: Synthesis, Acid–Base Behavior, Alkali Metal Ion Complexation, and Crystal Structure

Cited by 28 publications

References 63 publications

New ligand bearing preorganized binding side-arms interacting with ammonium cations: Synthesis, conformational studies and crystal structureElectronic supplementary information (ESI) available: molecular modeling studies. See http://www.rsc.org/suppdata/nj/b3/b306778e/

New ligand bearing preorganized binding side-arms interacting with ammonium cations: Synthesis, conformational studies and crystal structureElectronic supplementary information (ESI) available: molecular modeling studies. See http://www.rsc.org/suppdata/nj/b3/b306778e/

Crystal structure of diaquabis(1,10-phenanthroline-k2N, N')sodium chloride, [Na(H2O)2(C12H8N2)2]Cl

Small Janus dimer as electric field manipulated molecular clam switch and electric information storage unit

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