A Review on Perylene-3,4,9,10-Tetracarboxylic Acid Diimide Molecules

Birel, Özgür

doi:10.18466/cbayarfbe.319879

Cited by 5 publications

(5 citation statements)

References 35 publications

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“…Their solubilities in toluene at room temperature are <4 × 10 –6 , < 4 × 10 –6 , and <2 × 10 –5 M, respectively (Figure and Figure S14). ,,− Although we tried many different solution-based conditions using different catalysts, solvents, and temperatures, the reactions did not yield the coupling products (Schemes S3–S7). Pleasingly, the reaction of the perylenediimide dye 1i with 2f under the high-temperature ball-milling conditions proceeded to give the corresponding coupling product 3q in 37% yield (Figure A).…”

Section: Results and Discussionmentioning

confidence: 99%

Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides

et al. 2021

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Conventional organic synthesis generally relies on the use of liquid organic solvents to dissolve the reactants. Therefore, reactions of sparingly soluble or insoluble substrates are challenging and often ineffective. The development of a solventindependent solid-state approach that overcomes this longstanding solubility issue would provide innovative synthetic solutions and access to new areas of chemical space. Here, we report extremely fast and highly efficient solid-state palladium-catalyzed Suzuki− Miyaura cross-coupling reactions via a high-temperature ball-milling technique. This solid-state protocol enables the highly efficient cross-couplings of insoluble aryl halides with large polyaromatic structures that are barely reactive under conventional solution-based conditions. Notably, we discovered a new luminescent organic material with a strong red emission. This material was prepared via the solid-state coupling of Pigment violet 23, a compound that has so far not been involved in molecular transformations due to its extremely low solubility. This study thus provides a practical method for accessing unexplored areas of chemical space through molecular transformations of insoluble organic compounds that cannot be carried out by any other approach.

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Section: Results and Discussionmentioning

confidence: 99%

Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides

et al. 2021

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“…Aggregate morphologies of 1a, 1b, and 1c were investigated by transmission electron microscopy (TEM), employing phosphotungstic acid (PHA) 47 as a stain. TEM images of 1a showed irregularly shaped particles with a rough surface ranging from ca.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Characteristic absorption peaks originating from the PDI chromophore were observed for 1a , 1b , and 1c in (CH 3 ) 2 SO-rich solvent mixtures. For instance, 1a showed absorption peaks at 528 and 492 nm in (CH 3 ) 2 SO, which were denoted to the PDI (0,0) and (0,1) electronic transitions, respectively, as shown in Figure a. With increasing H 2 O contents in H 2 O/(CH 3 ) 2 SO solvents, an electronic absorption intensity of 1a slightly decreased along with a concomitant red shift of its absorption maximum.…”

Section: Resultsmentioning

confidence: 99%

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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“…Perylene-3,4,9,10-tetracarboxylic diimide (PDI) and its derivatives have been extensively applied to fabricate diverse electronic devices based on their extraordinary physicochemical properties, easy functionalization, and extremely low price (Perrin and Hudhomme, 2011; Birel, 2017). Fan et al (2015) constructed an efficient PDI-based NIR-absorptive contrast nanoagent enveloped by micelle for PA imaging of deep brain tumor in living mice.…”

Section: Optically Active Nanomedicine For Bioimagingmentioning

confidence: 99%

Optically Active Nanomaterials for Bioimaging and Targeted Therapy

Yang

Wang

Wan

et al. 2019

Front. Bioeng. Biotechnol.

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Non-invasive tracking for monitoring the selective delivery and transplantation of biotargeted agents in vivo has been employed as one of the most effective tools in the field of nanomedicine. Different nanoprobes have been developed and applied to bioimaging tissues and the treatment of diseases ranging from inflammatory and cardiovascular diseases to cancer. Herein, we will review the recent advances in the development of optics-responsive nanomaterials, including organic and inorganic nanoparticles, for multimodal bioimaging and targeted therapy. The main focus is placed on nanoprobe fabrication, mechanistic illustrations, and diagnostic, or therapeutical applications. These nanomedicine strategies have promoted a better understanding of the biological events underlying diverse disease etiologies, thereby facilitating diagnosis, illness evaluation, therapeutic effect, and drug discovery.

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A Review on Perylene-3,4,9,10-Tetracarboxylic Acid Diimide Molecules

Cited by 5 publications

References 35 publications

Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides

Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides

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

Optically Active Nanomaterials for Bioimaging and Targeted Therapy

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