FluorescentJ-type Aggregates and Thermotropic Columnar Mesophases of Perylene Bisimide Dyes

Würthner, Frank; Thalacker, Christoph; Diele, Siegmar; Tschierske, Carsten

doi:10.1002/1521-3765(20010518)7:10<2245::aid-chem2245>3.0.co;2-w

Cited by 622 publications

(504 citation statements)

References 72 publications

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“…The same conclusions have also been outlined by Neuteboom and coworkers 79 when studying the optical features of polytetrahydrofuran substituted PBI polymers in ODCB. Arnaud et al, 71 Würthner et al, 70,80,81 Datar et al, 82 and Yagai et al 75 reported as well the formation of this red-shifted band due to selfassembled/polymeric PBI in solutions.…”

Section: Resultsmentioning

confidence: 99%

Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

et al. 2014

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The synthesis, characterization and metal complexation of a new class of perylene bisimides (PBIs) as an integral part of ethylenediaminetetraacetic acid (EDTA) are reported. The simplest representative, namely derivative 1a, was synthesized both by a convergent as well as a direct approach while the elongated derivatives, 1b and 1c, were obtained only via a convergent synthetic pathway. All these new prototypes of water-soluble perylenes are bolaamphiphiles and were fully characterized by 1 H-and 13 C-NMR spectroscopy, matrix assisted laser desorption ionization-time of flight (MALDI-TOF) mass spectrometry and IR spectroscopy. In order to acquaint ourselves with the behaviour in solution of our PBIs bearing dendritic wedges, the simplest derivative, 1a, was chosen and tested by means of UV/Vis and fluorescence spectroscopy as well as by zeta-potential measurements. A photoexcitation induced intramolecular photo-electron transfer (PET) can be observed in these molecules. Therefore their potential applications as sensors can be imagined. Model compound 1a efficiently coordinates trivalent metal cations both in water and dimethyl sulfoxide (DMSO). Significantly, the effects of the complexation strongly depend on the aggregation state of the PBI molecules in solution. As a matter of fact, in water, the presence of M 3+ ions triggers the formation of light emitting supramolecular aggregates (excimers). On the other hand, in DMSO-rich solutions metal complexation leads to the suppression of the PET and leads to a strong fluorescence enhancement.

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Section: Resultsmentioning

confidence: 99%

Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

et al. 2014

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“…42 Many research groups have attempted to enhance the emission from the pyrene core in the solid state by modifying the molecular structures. 43 Sterically congested mesityl substituents can prevent undesirable face-to-face π-stacking, so that self-quenching is impeded to permit efficient emission.…”

Section: 11mentioning

confidence: 99%

Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue

Matsumoto

Suzuki

Hayashi

et al. 2017

Bulletin of the Chemical Society of Japan

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she was a researcher of PRESTO, JST, and then a group leader of CREST project (2010)(2011)(2012)(2013)(2014)(2015)(2016), JST, on "Construction of organic thin-film solar cells with innovative solutionprocessible organic materials". Her current research focuses on the development of functional organic materials including solution-processable molecular materials for organic electronics applications, large acenes and bottom-up synthesis of graphene nanoribbons. AbstractThe structure and electronic features of neutral and positively charged pyrene and perylene derivatives were explored. The radical cation of 1,3,6,8-tetraarylpyrene 1 was examined by ESR, UVvisNIR spectroscopy and theoretical calculations. The addition of 2 equiv of oxidant to 1 resulted in the formation of dication 1 2+. The single-crystal X-ray structure of 1 2+ proved that the aromatic part relocates from biphenyl unit to naphthyl unit upon 2e ¹ oxidation of 1. We have also investigated the oxidation processes of 3,9-diarylperylene 2 and 3,10-diarylperylene 3. The radical cations of 2•+ and 3 •+ showed ESR signals and the spin densities were proven to delocalize at 3,4,9,10-positions. In the case of doubly charged 3,9-diarylperylene, we could find the anthracene structure in the core, while the phenanthrene skeleton appeared in two-electron oxidized 3,10-diarylperylene. Finally we validated this phenomenon to apply for the higher analogue terrylene, discovering its large aromaticity relocation upon the 2e ¹ oxidation.

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“…[1][2][3][4] Perylene diimides (PDIs) derivatives effectively form supramolecular assemblies through p-p stacking interaction. [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] In particular, supramolecular assemblies based on calixarenePDI conjugates show efficient energy and electron transfer properties due to the well-defined rigid and electron-rich scaffolds of calixarenes. [22][23][24][25][26][27] We have prepared PDI derivatives with a high emission property in aqueous solutions.…”

Section: Introductionmentioning

confidence: 98%

Emission properties of cyclodextrin dimers linked with perylene diimide—effect of cyclodextrin tumbling

Takashima

Otsubo

et al. 2012

Polym J

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Perylene diimide (PDI) derivatives with cyclodextrins (PDI-CD 2 s) exhibit specific emission properties, which depend on the type of CDs in an aqueous solution. Herein we successfully create an emission film-kneaded PDI-CD 2 derivatives via effective tumbling of the altropyranose unit. PDI-6CD 2 s are crosslinked with PDI between 6-amino-CDs. Although the emission intensities of PDI-6CD 2 s in dimethyl sulfoxide are similar regardless of the type of CD, PDI-6cCD 2 has a relatively high emission intensity in aqueous solutions. In contrast, for PDIC 7 -3CD 2 s, which are linked with N,N'-bis(6-carboxylhexyl)perylene-3,4,9,10-tetracarboxyl diimide (BisC 7 -PDI) between 3-amino-CDs, the emission intensity of PDIC 7 -3bCD 2 is stronger than those of PDIC 7 -3aCD 2 , PDIC 7 -3cCD 2 , and PDI-6CD 2 s in aqueous solutions. The selective emission behavior of PDIC 7 -3CD 2 s is due to the formation of the pseudo[1]rotaxane dimer through tumbling of the altropyranose unit in an aqueous solution. PDIC 7 -3bCD 2 in the solid state does not demonstrate a distinctive emission due to self-quenching, whereas PDIC 7 -3bCD 2 kneaded into the polyvinyl alcohol (PVA) film exhibits a bright yellow emission. The order of the emission intensities of PDIC 7 -3CD 2 s kneaded into PVA films is similar to those in aqueous solutions. INTRODUCTIONRecently, supramolecular assemblies with extended aromatic compounds have attracted much attention. 1-4 Perylene diimides (PDIs) derivatives effectively form supramolecular assemblies through p-p stacking interaction. [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] In particular, supramolecular assemblies based on calixarenePDI conjugates show efficient energy and electron transfer properties due to the well-defined rigid and electron-rich scaffolds of calixarenes. [22][23][24][25][26][27] We have prepared PDI derivatives with a high emission property in aqueous solutions.Generally, PDI derivatives have low solubilities in aqueous solutions. Even if PDI derivatives are dissolved in aqueous solutions by introducing a hydrophilic group, the emission of PDI derivatives exhibit self-quenching in aqueous solutions due to the formation of supramolecular assemblies and folders. To create water-soluble and effective emission sensor materials with PDI derivatives, we have introduced CDs into the PDI motif. The CDs are a family of macrocyclic oligosaccharides; the most common are composed of 6 (a), 7 (b), or 8 (g) a-1,4-linked D-glucopyranose units. [28][29][30][31][32][33][34] The introduction of CDs should influence the molecular recognition property and increase the emission intensity. Although supramolecular assemblies based on permethylated CDPDI conjugates have been previously reported, 35-38 the formation of assemblies cannot prevent the decrease in the monomer emission intensity of the PDI units due

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FluorescentJ-type Aggregates and Thermotropic Columnar Mesophases of Perylene Bisimide Dyes

Cited by 622 publications

References 72 publications

Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue

Emission properties of cyclodextrin dimers linked with perylene diimide—effect of cyclodextrin tumbling

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