Supramolecular luminescent system based on 2-cyano-3(4-(diphenylamino)phenyl) acrylic acid: Chiral luminescent host for selective CH3CN sensor (original) (raw)
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The new tripodal ligand 1 containing the dansyl Cu 2+ , Co 2+ , Zn 2+ , and Cd 2+ ions, with concomitant pronounced changes in the fluorescence spectra. The chromophore has been synthesized and characterized. The intense luminescence characteristic of the chromophore is complexation is controlled by pH conditions: at neutral pH this ligand shows a remarkable selectivity towards Cu 2+ ions, maintained in the ligand structure, showing that no intramolecular interactions are present. This ligand has been suggesting a possible use for 1 as a luminescent chemosensor for this ion. shown to complex in acetonitrile/water solutions only with Fax: (internat.) ϩ 39(0)51/259456 E-mail: lprodi@ciam.unibo.it sorption and luminescence spectra of compound 2, while Eur.
Journal of Physical Organic Chemistry, 2010
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Supramolecular Luminescent Sensors
Chemical Reviews, 2018
There is great need for stand-alone luminescence-based chemosensors that exemplify selectivity, sensitivity, and applicability, and that overcome the challenges that arise from complex, realworld media. Discussed herein are recent developments toward that goal in the field of supramolecular luminescent chemosensors, including macrocycles, polymers, and nanomaterials. Specific focus is placed on the development of new macrocycle hosts since 2010, coupled with considerations of the underlying principles of supramolecular chemistry as well as analytes of interest and common luminophores. State-ofthe-art developments in the fields of polymer and nanomaterial sensors are also examined, and some remaining unsolved challenges in the area of chemosensors are discussed. Contents Changes in a detectable signal that occur in the presence of the analyte can refer to a broad variety of signaling elements and various types of read-outs, including changes in color (for colorimetric or absorption-based detection); 59-61 changes in the Raman spectral signal (for Raman-based detection); 62,63 changes in the mass of the sensor after a target analyte binds (for quartz crystal microbalance detection); 64-66 or changes in any other spectroscopic, 67 quantitative, 68 or analytical property. 69 Luminescence-based chemosensors refer to those sensors that respond to the presence of the target analyte with a detectable change in the luminescence signal, with the main types of luminescence being fluorescence, characterized as an allowed, singlet-to-singlet relaxation with photon emission, and phosphorescence, characterized as a forbidden, triplet-to-singlet relaxation with photon emission. More details about the mechanism of fluorescence and phosphorescence are discussed in Section 2.2, below. Luminescent chemosensors require a component that is photophysically active, in order for the target analyte to induce a measurable change in that photophysical activity. 70 The change of photophysical activity may occur through a change in the magnitude of emission intensity, the wavelength of the emission maximum, the quantum yield, or the relative ratios of various fluorescence/phosphorescence-emitting components. 71 Multiple types of emission changes can also occur simultaneously, 72,73 especially in complex detection environments. 74 This review focuses on luminescent chemosensors, including their rational design, and broad-ranging applications of such sensors in a variety of realms, including in materials science, biomedical imaging, and national security. It starts with a review of some of the underlying principles of chemosensors, including the non-covalent forces that govern such systems, and the mechanisms of recognition between an analyte and chemosensor via non-covalent interactions. From there, we will review particular classes of luminescent chemosensors, including luminescent macrocycles, luminescent polymers (both with conjugated luminescent backbones and with luminescent pendant side chains), and luminescent nanomaterials. Fluorescent chemosensors are much more common than those based on other types of luminescence, and thus the majority of discussions herein are focused on fluorescence. The concluding section of the review article includes a discussion of unsolved issues in the field of chemosensors, and how future directions of luminescent chemosensors might address those issues. Of note, the field of chemosensors in general, and fluorescent chemosensors in particular, is highly active with significant numbers of chemists publishing in this field. Readers are directed to other reviews on this important topic to supplement this one, including reviews by Anslyn,
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A new series of four isostructural mononuclear lanthanide complexes Ln(HPDH) 3 (H 2 O) 3 •H 2 O (Ln = Sm(III) 1, Eu(III) 2, Tb(III) 3 and Dy(III) 4; H 2 PDH = 6,7-dihydropyrido(2,3-d)pyridazine-5,8-dione) has been prepared and characterized by IR, elemental analysis, XRD and TG-DTA methods. Single crystal X-ray diffraction analysis of both complexes 1 and 3 revealed that the mononuclear discrete complexes form 3-D supramolecular networks via hydrogen bonds and offset stacking (-H⋯π) interactions. The photoluminescence study of the title complexes revealed the photoluminescent potential of the antenna ligand (H 2 PDH) toward the concerned lanthanide cations. The luminescence based sensing ability of the partially dehydrated complex Tb(HPDH) 3 (H 2 O) 3 3a towards small solvent molecules, along with its reusability, has been studied. Isopropyl alcohol was found to be an excellent sensitizer, while tetrahydrofuran was a highly quenching solvent with a first order behavior towards the photoluminescence intensity. The photoluminescence intensity was found to decrease with the increase of the dielectric constant and normalized Dimroth-Reichardt E T parameter values for protic solvents, while reverse behavior was observed for dipolar aprotic solvents. † Electronic supplementary information (ESI) available: 1 H NMR spectrum of ligand H 2 PDH, IR spectra of ligand and titled complexes, selected hydrogen bondings of complex 1, nonradiative deactivation mechanism, reusability of the complex 3a (Fig. S1 to S5) and crystal data of complex 1 and 3, selected bond lengths and bond angles and hydrogen bonding interactions in complex 1 (Tables S1 to S3). CCDC 960629 and 960631. For ESI and crystallographic data in CIF or other electronic format see
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Amplified chirality and Förster resonance energy transfer (FRET)-assisted chirality transfer from molecular to nanoscale level have been shown to play a vital role in co-assembled nanohelix for potential energy transfer in biological systems. Herein, we have constructed a chiral host-guest complex donor system for chiral amplification via induced chirality of pillar[5] arene host and loaded it with an achiral dye acceptor to demonstrate how chirality-assisted excitation energy transfer occurred in the supramolecular nanohelix system in an aqueous medium. We found that the individual chiral copolymeric guest could self-assemble into nanohelixes. In the presence of pillar[5]arene host, the formed supramolecular host-guest complex also proceeded to form long helical fibers via J-aggregation of pillar[5]arene; thus, causing amplified chirality. After loading an achiral dye acceptor into the host-guest complex donor, it achieved coassembled composite nanohelixes via electrostatic interactions and ordered stacking of the chromophoric dyes. In this hybrid supramolecular system, the loaded dye was uniformly dispersed, becoming the driving force for chirality transfer. Fascinatingly, this supramolecular system containing achiral dye could capture both chiral information and energy from the chiral donor, displaying supramolecular chirality and FRET-assisted amplified circularly polarized luminescence (CPL) in water with a large dissymmetry factor (g lum = 1.32 × 10 −2).
International Journal of the Society of Materials Engineering for Resources, 2000
jp Mono (R) or (S)-3-hydroxy-3phenylpropanoic acid modified ƒÀ cyclodextrins (CyDs, 1 and 2, respec tively) and their analogs of regioselectively bis-(R) and (S)3-hydroxy-3-phenylpropanoic acid modified ƒÀ-CyDs (3 and 4 , respectively) have been synthesizd to investigate their enantiometric discrimination of D,L-isomers. These host compounds show composedof pure monomer emission with peaks around 300 nm and 340 nm, of which the intensities are decreased or increased when a host-guest complexation occurs. The extent of fluorescence variation with a guest is employed to display the sensing ability of those hosts. Monosubstituted CyDs such as 1 and 2 show relatively higher positive parameter values for the guests such as (ƒÀ)-menthol (5, 6), (•})-camphor (7, 8), (•})2bromopropionic acid (9, 10), and (•})-prolone (13, 14), although disubstituted derivatives such as 3 and 4 exhibit negative parameter values for the guests examined, when they are examined their ability at 300 nm.
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Photophysics, Photochemical and Substitution Reactions- Recent Advances [Working Title]
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