Metal ion templated self-assembly of crown ether functionalized perylene bisimide dyes

Weißenstein, Annike; Würthner, Frank

doi:10.1039/c4cc09443c

Cited by 34 publications

(27 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The ammonium salts were prepared by dissolving the respective commercially available amino acids and dipeptides in 1 m aqueous HCl solution and subsequently freeze dried. PBI 1 was reported previously and prepared according to the literature procedure …”

Section: Resultsmentioning

confidence: 99%

“…As the primary recognition site for ammonium ions, we chose 18‐crown‐6 ether due to its strong affinity for primary ammonium cations through directional hydrogen bonding . Therefore, the PBI derivative 1 (Figure ) bearing two 18‐crown‐6 moieties at the 1,7‐bay positions and solubilizing ionic side chains at imide positions appeared to be a suitable fluorescent probe for the optical sensing of amino acids and peptides if additional π–π interactions (including van‐der‐Waals and charge transfer contributions) with amino acids containing aromatic groups take place. This possible second binding event should accordingly strengthen the molecular recognition of aromatic amino acids and peptides and, in addition, afford a fluorescence response, that is, quenching of fluorescence by PET process from the electron‐rich aromatic functional group of amino acid guest molecules to the electron‐poor PBI core.…”

Section: Introductionmentioning

confidence: 99%

“…The rationale behind this concept is that PBIs are outstanding fluorophores [17] with quantum yields of up to unity,b ut they are easily quenched by photoinduced electron transfer (PET) processes to electron-rich,a romatic covalently or non-covalentlyb ound subunits. [18] During the last years, appropriately functionalized PBI fluorophores have been employed for the molecular recognition of aromatic hydrocarbons throughh ostguest binding, [19] as chemosensors for metal ions, [20] and for the detection and sensing of DNA. [21] However, PBI fluorophores are barely used as molecular probesf or amino acids and peptides and the very few known examples dependo n the release of PBId yes from their non-fluorescent aggregates, for example, by embedment into hydrophobic protein pockets, [22a] or ac ysteines pecific replacement of Hg 2 + from PBI-Hg 2 + aggregates.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Optical Sensing of Aromatic Amino Acids and Dipeptides by a Crown‐Ether‐Functionalized Perylene Bisimide Fluorophore

Weißenstein

Saha‐Möller

Würthner

2018

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

The host-guest binding properties of a fluorescent perylene bisimide (PBI) receptor equipped with crown ether were studied in detail with a series of aromatic amino acids and dipeptides by UV/Vis, fluorescence and NMR spectroscopy. Fluorescence titration experiments showed that electron-rich aromatic amino acids and dipeptides strongly quench the fluorescence of the electron-poor PBI host molecule. Benesi-Hildebrand plots of fluorescence titration data confirmed the formation of host-guest complexes with 1:2 stoichiometry. Binding constants determined by global analysis of UV/Vis and fluorescence titration experiments revealed values between 10 m and 10 m in acetonitrile/methanol (9:1) at 23 °C. These data showed that amino acid l-Trp having an indole group and dipeptides containing this amino acid bind to the PBI receptor more strongly than other amino acids and dipeptides investigated here. For dipeptides containing l-Trp or l-Tyr, the binding strength is dependent on the distance between the ammonium group and the aromatic unit of the amino acids and dipeptides leading to a strong sensitivity for Ala-Trp dipeptide. 1D and 2D NMR experiments also corroborated 1:2 host-guest complexation and indicated formation of two diastereomeric species of host-guest complexes. The studies have shown that a properly functionalized PBI fluorophore functions as a molecular probe for the optical sensing of aromatic amino acids and dipeptides.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Optical Sensing of Aromatic Amino Acids and Dipeptides by a Crown‐Ether‐Functionalized Perylene Bisimide Fluorophore

Weißenstein

Saha‐Möller

Würthner

2018

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

“…Moreover, PDI-5 and PDI-5-Cu 2+ (2:1) complex showed significant fluorosolvatochromism that can be used to differentiate organic solvents. Würthner [12] reported on a unique fluorescence turn-off sensor based on PDI 6 modified with 15-crown-5 ether (Figure 4a) that demonstrated selective detection of Ba 2+ ion. The sensing mechanism is due to the metal ion-induced self-assembly of PDI molecules, which in turn causes fluorescence quenching (turn-off).…”

Section: Ib Group (Cu 2+ )mentioning

confidence: 99%

Perylene Diimide-Based Fluorescent and Colorimetric Sensors for Environmental Detection

Chen

Xue

Gao

et al. 2020

Sensors

View full text Add to dashboard Cite

Perylene tetracarboxylic diimide (PDI) and its derivatives exhibit excellent thermal, chemical and optical stability, strong electron affinity, strong visible-light absorption and unique fluorescence on/off features. The combination of these features makes PDIs ideal molecular frameworks for development in a broad range of sensors for detecting environmental pollutants such as heavy metal ions (e.g., Cu 2+ , Cd 2+ , Hg 2+ , Pd 2+ , etc.), inorganic anions (e.g., F − , ClO 4 − , PO 4 − , etc.), as well as poisonous organic compounds such as nitriles, amines, nitroaromatics, benzene homologues, etc. In this review, we provide a comprehensive overview of the recent advance in research and development of PDI-based fluorescent sensors, as well as related colorimetric and multi-mode sensor systems, for environmental detection in aqueous, organic or mixed solutions. The molecular design of PDIs and structural optimization of the sensor system (regarding both sensitivity and selectivity) in response to varying analytes are discussed in detail. At the end, a perspective summary is provided covering both the key challenges and potential solutions for the future development of PDI-based optical sensors.

show abstract

“…Perylene diimides( PDIs),w hich form an interesting class of functional organicd yes, have been used as high-performance pigments, [10,11] supramolecularh osts, [12][13][14][15][16][17] and in optoelectronic devices. [18,19] The functionalization of PDIs at bay-, peri-, ortho-, and N-terminal positions is being performed to increaset he solubility of PDIs in organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Singh

Mittal

Bhargava

et al. 2017

Chemistry An Asian Journal

View full text Add to dashboard Cite

The detection and quantification of spermine in clinical practice is important for early diagnosis of many diseases. Chromatographic and immunoassay-based methods are commonly used. However, a fluorescence-based assay could provide real-time detection. Herein, the synthesis and aggregation properties of a dicationic perylene probe (N -dodecyl-N -(4-phenyl)benzimidazolium-functionalized perylenediimide (DAB-PDI)) used to develop a fluorescent "turn-on" ensemble for the detection of spermine are discussed. The fluorescence of DAB-PDI (10 μm, Φ=0.55) is efficiently quenched by negatively charged sodium dodecylsulfate (SDS) through the formation of ionic self-assembled aggregates (charge ratio of negative (N) in SDS to positive (P) in DAB-PDI (N/P)=9). This negatively charged ionic self-assembly between DAB-PDI and SDS has been characterized by using photophysical, microscopic, dynamic light scattering, isothermal titration calorimetry, and HRMS techniques. The addition of spermine to this ensemble solution results in the breakdown of the DAB-PDI-SDS ensemble owing to strong binding of spermine with SDS and, as a result, the fluorescence of DAB-PDI is recovered. This ensemble exhibits high sensitivity and selectivity for spermine detection in water, urine, and blood serum. The lowest limit of detection is 27.5 nm, which is at least about 36 times lower than that required for early diagnosis of cancer (1 to 10 μm for urinary spermine).

show abstract

Metal ion templated self-assembly of crown ether functionalized perylene bisimide dyes

Cited by 34 publications

References 35 publications

Optical Sensing of Aromatic Amino Acids and Dipeptides by a Crown‐Ether‐Functionalized Perylene Bisimide Fluorophore

Optical Sensing of Aromatic Amino Acids and Dipeptides by a Crown‐Ether‐Functionalized Perylene Bisimide Fluorophore

Perylene Diimide-Based Fluorescent and Colorimetric Sensors for Environmental Detection

Ionic Self‐Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples

Contact Info

Product

Resources

About