Solvatochromic Pyrene Analogues of Prodan Exhibiting Extremely High Fluorescence Quantum Yields in Apolar and Polar Solvents

Niko, Yosuke; Kawauchi, Susumu; Konishi, Gen‐ichi

doi:10.1002/chem.201301020

Cited by 145 publications

(86 citation statements)

References 72 publications

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“…23 In this regard, there are mainly two fluorescence-based approaches to study the interaction between watersoluble host and biomolecules. 44 In fact, such class of fluorescent dyes are very useful for probing diverse physical and biochemical processes. 41 On the other hand, the second approach, which is an indirect method, rely on the careful choice of a fluorescent dye and the modulation of its photophysical properties upon interaction with host as well as with biomolecule of interest.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular guest relay using host-protein nanocavities: an application of host-induced guest protonation

et al. 2016

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Small drug molecules and other important metabolites are delivered via a suitable carrier protein-mediated transport through a specific receptor. The process is highly coordinated and associated with complexation induced properties of deliverable molecules. To get a molecular insight, in this report, we tried to mimic the delivery process to know how the carrier protein relocates the drug molecule from the macrocyclic host cavity to its binding pocket and how the electronic and the chemical properties of the guest get altered. Bovine and human serum albumin (BSA and HSA) were used as the model carrier proteins which can snatch out 6-propanoyl-2-(N,N-dimethylamino)naphthalene (PRO), dye used as a drug model (known to bind at the drug-binding pocket of the carrier protein), from the cucurbit[7]uril (CB7) cavity, a potential drug delivery carrier. Prior to performing the fluorescence-based bio-supramolecular relocation assay using BSA and HSA, CB7 and PRO, we have investigated the effect of CB7 encapsulation and protonation on the fluorescence properties of PRO. A significant shift in the pKa value from 3.4 to 6.6 (ca. 3.2 logarithmic units) of PRO was observed upon encapsulation with CB7, which causes a huge fluorescence quenching even at neutral pH. The binding affinity of protonated and neutral PRO for CB7 also confirms a 3.2 unit shift in the acid-dissociation constant. A displacement assay using a strong CB7 binder, viz., 1,6-diaminohexane, confirms encapsulation of PRO in the CB7 cavity. Encapsulation of neutral PRO by CB7 shows a significant fluorescence enhancement accompanied by a ∼35 nm blue shift in the emission maxima.

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Section: Introductionmentioning

confidence: 99%

Supramolecular guest relay using host-protein nanocavities: an application of host-induced guest protonation

et al. 2016

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“…The strong increase of fluorescence quantum yield was also reported. Very high quantum yield in both polar and apolar solvents together with strong solvatochromy was found for Prodan analog with pyrene core (Niko et al 2013). These novel derivatives with superior spectroscopic and solvatochromic properties are expected to totally substitute Prodan in molecular probing studies.…”

Section: The Environment-sensitive (Solvatochromic) Dyesmentioning

confidence: 90%

Molecular-Size Fluorescence Emitters

Demchenko

2015

Introduction to Fluorescence Sensing

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A variety of fluorescent and luminescent materials in the form of molecules, their complexes and nanoparticles are available for implementation as response units into sensing and imaging technologies and we discuss their general properties that are essential for these applications. Organic dyes were the first and remain to be the most popular emitters used with these purposes. Their labeling and responsive properties are overviewed. Natural fluorescent proteins and their engineered analogues incorporate organic fluorophores that are synthesized spontaneously from the polypeptide chain inside the living cells without the need of their intrusion, as the gene products. They resulted in revolutionary advancement in cell imaging and show good prospects in sensing and reporting on cellular processes. Organic heterocyclic compounds can incorporate metal ions generating long-living luminescence. Moreover, noble metal particles of a very small size exhibit unique light-absorbing and fluorescent emission properties. In this Chapter we focus on these types of fluorophores that possess subnanometer dimensions and display single type of absorption-emission cycle. The more complex nanostructures and nanocomposites will be overviewed in Chaps. 5 and 6 that follow. Fluorophores and Their Characteristics General Properties of Fluorescent DyesIn view of tremendous diversity of structures, chemical reactivities and spectroscopic properties, one needs certain practically useful criteria for the dye selection for the purpose of sensing and imaging. They can be formulated in the form of spectroscopic parameters that have to be optimized. It is the parameter describing the ability of molecule to absorb light at a particular wavelength. The absorbance E measured at any wavelength on spectrophotometer is proportional to the dye concentration c (in mol/l) and the light path length in a sample l (in cm). In this relation, ε plays the role of coefficient of proportionality, so that E = εcl. The value of molar absorbance is obtained by purifying and drying the dye, dissolving it at low concentration and measuring E on a spectrophotometer. The broadly used term extinction includes absorbance and light scattering. Absorbance is a unique characteristic of a molecule under certain environmental conditions. In general, the bigger the fluorophore size, the greater is the probability that the photon will be absorbed.The value of ε max at the maximum of absorption band is the common characteristic of the light-absorbing power of the dye. The dye 'brightness' that determines the absolute sensitivity of fluorescence detection (Wetzl et al. 2003) is the product of molar absorbance and quantum yield, Φ. The absorbance is related to optical cross-section and for organic dyes, ε max varies from ca. 10 3 l mol −1 cm −1 for small dyes, such as coumarins to ca. 10 5 l mol −1 cm −1 for larger fluorophores such as cyanines and phthalocyanines (Lavis and Raines 2008). It should be selected as high as possible, but the limiting factor is the fluorophore size. Us...

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“…To date, many environment‐sensitive luminescent materials with various electron donor and acceptor structures (D−A) have been reported . Konishi and coworkers reported strong solvatochromism and high luminescence quantum yield using a D–A type pyrene derivative . Xiong achieved bio‐sensing TADF materials with long emission lifetimes (> 1 μs) …”

Section: Figurementioning

confidence: 99%

Asymmetric Color‐Changeable Luminophore with Donor–Acceptor–Donor Structure for Solvent and Temperature Sensitive Properties

et al. 2018

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An asymmetric donor–acceptor–donor (D–A–D) type organic luminophore is reported for solvent and temperature sensors. The electronic absorption and luminescence properties of the luminophore were assessed from its electronic absorption and luminescence spectra, which depended on the external environment. The D–A–D luminophore showed environment‐sensitive charge transfer fluorescence based on structural transformation through excited singlet states. Characteristic D–A–D phosphorescence was also observed at 494 nm, which was shorter than that of the D–A–D fluorescence (502 nm). In this study, the novel photophysical properties of a D–A–D‐type luminophore induced by its asymmetric electronic structure are described.

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Solvatochromic Pyrene Analogues of Prodan Exhibiting Extremely High Fluorescence Quantum Yields in Apolar and Polar Solvents

Cited by 145 publications

References 72 publications

Supramolecular guest relay using host-protein nanocavities: an application of host-induced guest protonation

Supramolecular guest relay using host-protein nanocavities: an application of host-induced guest protonation

Molecular-Size Fluorescence Emitters

Asymmetric Color‐Changeable Luminophore with Donor–Acceptor–Donor Structure for Solvent and Temperature Sensitive Properties

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