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New fluorescent perylene bisimide indicators--a platform for broadband pH optodes.

ABSTRACT: Asymmetric perylene bisimide (PBI) dyes are prepared and are shown to be suitable for the preparation of fluorescence chemosensors for pH. They carry one amino-functional substituent which introduces pH sensitivity via photoinduced electron transfer (PET) while the other one increases solubility. The luminescence quantum yields for the new indicators exceed 75% in the protonated form. The new indicators are non-covalently entrapped in polyurethane hydrogel D4 and poly(hydroxyalkylmethacrylates). Several PET functions including aliphatic and aromatic amino groups were successfully used to tune the dynamic range of the sensor. Because of their virtually identical spectral properties, various PBIs with selected PET functions can easily be integrated into a single sensor with enlarged dynamic range (over 4 pH units). PBIs with two different substitution patterns in the bay position are investigated and possess variable spectral properties. Compared with their tetrachloro analogues, tetra-tert-butyl-substituted PBIs yield more long-wave excitable sensors which feature excellent photostability. Cross-sensitivity to ionic strength was found to be negligible. The practical applicability of the sensors may be compromised by the long response times (especially in case of tetra-tert-butyl-substituted PBIs).

SUBMITTER: Aigner D

PROVIDER: S-EPMC3100492 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Ultrabright Red-Emitting Photostable Perylene Bisimide Dyes: New Indicators for Ratiometric Sensing of High pH or Carbon Dioxide.

Project description:New pH-sensitive perylene bisimide indicator dyes were synthesized and used for fabrication of optical sensors. The highly photostable dyes show absorption/emission bands in the red/near-infrared (NIR) region of the electromagnetic spectrum, high molar absorption coefficients (up to 100?000?m-1 ?cm-1 ), and fluorescence quantum yields close to unity. The absorption and emission spectra show strong bathochromic shifts upon deprotonation of the imidazole nitrogen atom, which makes the dyes promising as ratiometric fluorescent indicators. Physical entrapment of the indicators into a polyurethane hydrogel enables pH determination at alkaline pH values. It is also shown that a plastic carbon dioxide solid-state sensor can be manufactured by immobilization of the pH indicator in a hydrophilic polymer, along with a quaternary ammonium base. The influences of the plasticizer, different lipophilic bases, and humidity on the sensitivity of the sensor material are systematically investigated. The disubstituted perylene, particularly, features two deprotonation equilibria, enabling sensing over a very broad pCO2 range of 0.5 to 1000?hPa.

| S-EPMC6099519 | biostudies-other

Mechanoresponsive Self-Assembled Perylene Bisimide Films.

Project description:In this work, self-assembled amino-acid appended perylene bisimides (PBIs) have been studied that when processed into thin films change their resistivity in response to being bent. The PBIs assemble into structures in water and form thin films upon drying. These normally delicate thin films can be tolerant to bending, depending on the aggregates they form. Furthermore, the films then reversibly change their resistivity in response to this mechanical stimulus. This change is proportional to the degree of bending of the film giving them the potential to be used quantitatively to measure mechanical movement, such as in wearable devices.

| S-EPMC7522684 | biostudies-literature

Self-sorted Oligophenylvinylene and Perylene Bisimide Hydrogels.

Project description:We describe two component hydrogels with networks composed of self-sorted fibres. The component gelators are based on 1,4-distyrylbenzene (OPV3) and perylene bisimide (PBI) units. Self-sorted gels can be formed by a slow decrease in pH, which leads to sequential assembly. We demonstrate self-sorting by NMR, rheology and small angle X-ray scattering (SAXS). Photoconductive xerogels can be prepared by drying these gels. The wavelength response of the xerogel is different to that of the PBI alone.

| S-EPMC5566499 | biostudies-literature

Fluorescent nano-optodes for glucose detection.

Project description:We have designed fluorescent nanosensors based on ion-selective optodes capable of detecting small molecules. By localizing the sensor components in a hydrophobic core, these nanosensors are able to monitor dynamic changes in concentration of the model analyte, glucose. The nanosensors demonstrated this response in vitro and also when injected subcutaneously into mice. The response of the nanosensors tracked changes in blood glucose levels in vivo that were comparable to measurements taken using a glucometer. The development of these nanosensors offers an alternative, minimally invasive tool for monitoring glucose levels in such fields as diabetes research. Furthermore, the extension of the ion-selective optode sensor platform to small molecule detection will allow for enhanced monitoring of physiological processes.

| S-EPMC2862111 | biostudies-literature

Hydrogen-bonded perylene bisimide J-aggregate aqua material.

Project description:A new twelvefold methoxy-triethyleneglycol-jacketed tetraphenoxy-perylene bisimide (MEG-PBI) amphiphile was synthesized that self-assembles into two types of supramolecular aggregates in water: red-coloured aggregates of low order and with weak exciton coupling among the PBIs and blue-coloured strongly coupled J-aggregates consisting of a highly ordered hydrogen-bonded triple helix of PBIs. At room temperature this PBI is miscible with water at any proportions which enables the development of robust dye aggregates in solution, in hydrogel states and in lyotropic liquid crystalline states. In the presence of 60-95 wt% water, self-standing coloured hydrogels exhibit colour changes from red to blue accompanied by a fluorescence light-up in the far-red region upon heating in the range of 30-50 °C. This phenomenon is triggered by an entropically driven temperature-induced hydrogen-bond-directed slipped stacking arrangement of the MEG-PBI chromophores within structurally well-defined J-aggregates. This versatile aqua material is the first example of a stable PBI J-aggregate in water. We anticipate that this study will open a new avenue for the development of biocompatible functional materials based on self-assembled dyes and inspire the construction of other hydrogen-bonded supramolecular materials in the highly competitive solvent water.

| S-EPMC6124903 | biostudies-other

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties.

Project description:Three asymmetric amino-substituted perylene bisimide dyes with different n-alkyl chain lengths (n = 6, 12, or 18), 1-(N,N-dialkylamino)perylene bisimides (1a-1c), were synthesized under mild condition in high yields and were characterized by ¹H NMR, ¹³C NMR (nuclear magnetic resonance), HRMS (High Resolution Mass Spectrometer), UV-Vis and fluorescence spectra, as well as cyclic voltammetry (CV). These molecules show intense green color in both solution and solid state and are highly soluble in dichloromethane and even in nonpolar solvents, such as hexane. The shapes of the absorption spectra of 1a-1c in solid state and in solution were found to be virtually the same, indicating that the long alkyl chains could efficiently prevent aggregation. They exhibit a unique charge transfer emission in the near-infrared region, of which the peak wavelengths show strong solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1-aminoperylene bisimide (2). Furthermore, all of the compounds exhibit two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory (DFT) calculations performed on these dyes are reported in order to rationalize their molecular structures and electronic properties.

| S-EPMC5456190 | biostudies-other

Deracemization of Carbohelicenes by a Chiral Perylene Bisimide Cyclophane Template Catalyst.

Project description:Deracemization describes the conversion of a racemic mixture of a chiral molecule into an enantioenriched mixture or an enantiopure compound without structural modifications. Herein, we report an inherently chiral perylene bisimide (PBI) cyclophane whose chiral pocket is capable of transforming a racemic mixture of [5]-helicene into an enantioenriched mixture with an enantiomeric excess of 66 %. UV/Vis and fluorescence titration studies reveal this cyclophane host composed of two helically twisted PBI dyes has high binding affinities for the respective homochiral carbohelicene guests, with outstanding binding constants of up to 3.9×1010 m-1 for [4]-helicene. 2D NMR studies and single-crystal X-ray analysis demonstrate that the observed strong and enantioselective binding of homochiral carbohelicenes and the successful template-catalyzed deracemization of [5]-helicene can be explained by the enzyme-like perfect shape complementarity of the macrocyclic supramolecular host.

| S-EPMC8362091 | biostudies-literature

Polycondensation of a Perylene Bisimide Derivative and L-Malic Acid as Water-Soluble Conjugates for Fluorescent Labeling of Live Mammalian Cells.

Project description:Based on simple mixing and polymerization of a hydroxyl-containing derivative of perylene bisimide (PBI) and l-malic acid, here, we demonstrate a new type of dye-polymer conjugate, PBI-poly(α,β-malic acid) (PBI⁻PMA). Benefiting from the excellent water-solubility of weak polyanionic PMA structure and the high fluorescence of PBI, the PBI-PMA conjugates readily dissolve in water, displaying strong pH-dependent fluorescence with the highest intensity at pH 6. Due to the excellent biocompatibility of PMA, those conjugates showed low cytotoxicity on L929 cells. Using L929 and HeLa cells, we also confirmed that the PBI-PMA-labeled cells display intense fluorescence. Overall, the PBI-PMA conjugate demonstrates high potential as a cell labeling agent with its synthesis ease, good solubility in aqueous medium, low cytotoxicity, and high fluorescence.

| S-EPMC6415357 | biostudies-literature

Organic Acid Regulated Self-Assembly and Photophysical Properties of Perylene Bisimide Derivatives.

Project description:In this work, perylene bisimide derivatives (PBI-1 and PBI-2) with tertiary amine groups were designed and synthesized. To control the final morphologies and properties of their aggregates, seven kinds of organic acids were used to alter the self-assembly environment. The influence of organic acids on the morphology of the aggregates was investigated. Photophysical properties of the aggregates were markedly affected by the kind and concentration of the organic acid. The thermal and gas sensitivities of the PBI-1 aggregates were studied with the use of UV-visible spectroscopy and digital imaging. The shift of the UV-visible spectra varied with time, temperature, acid type and acid concentration. Furthermore, PBI-1 aggregates showed a red-to-blue color change after addition of seven organic acids, whereas the color of the PBI-2 aggregates remained red. These changes of morphologies, photophysical properties and their thermal and gas sensitivities make these aggregates potentially useful in the fields of optoelectronics or sensors.

| S-EPMC7178315 | biostudies-literature

Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area.

Project description:A series of perylene bisimide (PBI) dyes bearing various aryl substituents in 1,6,7,12 bay positions has been synthesized by Suzuki cross-coupling reaction. These molecules exhibit an exceptionally large and conformationally fixed twist angle of the PBI π-core due to the high steric congestion imparted by the aryl substituents in bay positions. Single crystal X-ray analyses of phenyl-, naphthyl- and pyrenyl-functionalized PBIs reveal interlocked π-π-stacking motifs, leading to conformational chirality and the possibility for the isolation of enantiopure atropoisomers by semipreparative HPLC. The interlocked arrangement endows these molecules with substantial racemization barriers of about 120 kJ mol-1 for the tetraphenyl- and tetra-2-naphthyl-substituted derivatives, which is among the highest racemization barriers for axially chiral PBIs. Variable temperature NMR studies reveal the presence of a multitude of up to fourteen conformational isomers in solution that are interconverted via smaller activation barriers of about 65 kJ mol-1 . The redox and optical properties of these core-twisted PBIs have been characterized by cyclic voltammetry, UV/Vis/NIR and fluorescence spectroscopy and their respective atropo-enantiomers were further characterized by circular dichroism (CD) and circular polarized luminescence (CPL) spectroscopy.

| S-EPMC8456824 | biostudies-literature

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