Retention of perylene diimide optical properties in solid-state materials through tethering to nanodiamonds

Almuhana, Asia; Langer, Philipp; Griffin, Sarah L.; Lodge, Rhys W.; Rance, Graham A.; Champness, Neil R.

doi:10.1039/d1tc02577e

Cited by 3 publications

(2 citation statements)

References 53 publications

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“…Hence, in addition to 1a and 1b , especially nonionic 1c tends to form self-aggregates in H 2 O-rich solvent mixtures because there is no electrostatic repulsion for 1c . On the other hand, there are no meaningful differences between 1a , 1b , and 1c in a (CH 3 ) 2 SO-rich solvent mixture (80%), and these results show that 1a , 1b , and 1c exist in a monomeric form. − …”

Section: Resultsmentioning

confidence: 79%

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

Hayashida,

Araki,

Miyazaki

2024

J. Org. Chem.

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Cationic, anionic, and nonionic cyclophane dimers, 1a, 1b, and 1c, covalently linked with fluorescent perylene diimide were synthesized, respectively, as a host for aggregation-induced multivalent effects on guest-binding. These PDI-linked cyclophane dimers 1a and 1b, especially 1c, formed self-aggregates in H 2 O-rich solvents through π-stacking interactions. Critical aggregation concentrations of 1a, 1b, and 1c in H 2 O were 4.0 × 10 −6 , 4.0 × 10 −6 , and less than 0.1 × 10 −6 M, respectively. The selfaggregates of the PDI-linked cyclophane dimers in H 2 O were several hundred nanometers in size by DLS and TEM measurements. In an aggregated state, 1a exhibited guest-binding abilities toward hydrophobic guests, such as 6-p-toluidinonaphthalene-2-sulfonate and 6-anilino-naphthalene-2-sulfonate. Moreover, anion-induced agglutination of 1a was observed upon the addition of phosphate ions, and its effectiveness was as follows: ATP > ADP > H 2 P 2 O 7 2− > AMP ≈ PO 4 3− > HPO 4 2− > H 2 PO 4 − . The contribution of the adenine base of the nucleotides as a guest moiety used for effective agglutination was confirmed by 1 H NMR spectroscopy.

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Section: Resultsmentioning

confidence: 79%

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

Hayashida,

Araki,

Miyazaki

2024

J. Org. Chem.

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“…Concerning the choice of chromophore linkers, rylene dyes are a very prominent class of organic dye molecules. Initially applied for industrial use as red dyes and as pigments in automotive finishes [15], they became widely used in manifold industrial applications as well as in modern research [16], due to their outstanding chemical, thermal, and optical stability [17][18][19]. In addition, they exhibit remarkable optoelectronic properties, e.g., as excellent light-harvesting materials, since they strongly absorb visible light with high fluorescence quantum yields in solution [20].…”

Section: Introductionmentioning

confidence: 99%

A Perylenediimide-Based Zinc-Coordination Polymer for Photosensitized Singlet-Oxygen Generation

et al. 2022

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In the face of anthropogenic global warming the design and synthesis of materials, which enable energy transfer processes using sunlight as an energy source, are of high interest. Perylenediimides are a highly absorbing class of chromophores suitable for sunlight absorption and conversion. Therefore, metal–organic frameworks (MOFs) and coordination polymers (CPs) with incorporated organic perylene chromophores are highly interesting materials both for applied, but also fundamental, photophysical research. MOFs/CPs have the advantage of a modular adjustability of interchromophoric distances and angles, and the choice of metal nodes can be used to further tune the material towards the desired photophysical properties. In the present paper, we present a study using a reported organic perylenediimide (PDI) chromophore (H2tpdb) as a linker to be incorporated into coordination polymer and test towards applicability within the photochemical 1O2 generation. In detail, a novel zinc 2D -coordination polymer Zn(tpdb)(DMF)3 is reported, which is synthesized using a solvothermal synthesis with Zn(NO3)2 and a ditopic organic perylene linker. Both the linker and Zn-CP are fully characterized, including SC-XRD, showing a strong aggregation of tightly packed chromophores in the solid state. The photophysical properties are examined and discussed, including the observed shifts within the absorption spectra of the CP are compared to the linker in solution. These shifts are mainly attributed to the for PDIs known H-type aggregation and an additional charge transfer in the framework structure, causing a limited quantum yield of the emission. Finally, the photosensitization of triplet oxygen to singlet oxygen using 1,3-diphenylisobenzofurane (DBPF) as a trapping agent is investigated both for the free linker and the Zn-CP, showing that the perylene chromophore is an efficient photosensitizer and its activity can, in principle, be retained after its incorporation in the coordination polymer.

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Fluorescent detection of tartrazine based on the supramolecular self-assembly of cationic perylene diimide

et al. 2023

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Retention of perylene diimide optical properties in solid-state materials through tethering to nanodiamonds

Abstract: The synthesis of nanodiamond-perylene diimide composites is reported. Suitably hydroxyl-functionalised perylene diimides (PDIs) are reacted with carboxylic acid functionalised nanodiamonds (NDs) through ester formation. The ND-PDI nanocomposite materials were characterised...

Cited by 3 publications

References 53 publications

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

Self-Aggregation, Enhanced Guest-Binding Behavior, and Anion-Induced Agglutination of Cyclophane Dimers Linked with Florescent Perylene Diimide

A Perylenediimide-Based Zinc-Coordination Polymer for Photosensitized Singlet-Oxygen Generation

Fluorescent detection of tartrazine based on the supramolecular self-assembly of cationic perylene diimide

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