Formation of Two Homo‐chromophoric H‐Aggregates in DNA‐Assembled Alternating Dye Stacks

Winiger, Christian B.; Langenegger, Simon M.; Calzaferri, Gion; Häner, Robert

doi:10.1002/anie.201410041

Cited by 52 publications

(41 citation statements)

References 39 publications

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“…In ethanol, the oligomer is very soluble and the spectrum closely resembles that of the phenanthrene monomer (Supporting Information). [48][49][50][51][52][53] Phenanthrene aggregation leads to the disappearance of the 270 nm band and the occurrence of an H-band (243 nm). [48][49][50][51][52][53] Phenanthrene aggregation leads to the disappearance of the 270 nm band and the occurrence of an H-band (243 nm).…”

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confidence: 99%

Light‐Harvesting Nanotubes Formed by Supramolecular Assembly of Aromatic Oligophosphates

2016

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A 2,7-disubstituted phosphodiester-linked phenanthrene trimer forms tubular structures in aqueous media. Chromophores are arranged in H-aggregates. Incorporation of small quantities of pyrene results in the development of light-harvesting nanotubes in which phenanthrenes act as antenna chromophores and pyrenes as energy acceptors. Energy collection is most efficient after excitation at the phenanthrene H-band. Fluorescence quantum yields up to 23 % are reached in pyrene doped, supramolecular nanotubes.

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confidence: 99%

Light‐Harvesting Nanotubes Formed by Supramolecular Assembly of Aromatic Oligophosphates

2016

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“…ds(Sp/PN) showed broadened absorption bands from λ =600 to 800 nm of the pyrrolidine‐substituted PDI . The absorption spectrum of dsDNA containing both PH and PN (PH/PN) was almost consistent with the superposition of the spectra of PH and PN; this means that no strong electronic coupling exists in the ground state between PH and PN . The fluorescence spectra of the PDI/DNA conjugates are shown in Figure b.…”

Section: Resultsmentioning

confidence: 84%

Rapid Electron Transfer of Stacked Heterodimers of Perylene Diimide Derivatives in a DNA Duplex

Takada

Ishino

Takata

et al. 2018

Chemistry A European J

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The preparation of homo- and heterocomplexes composed of the parent perylene diimide (PH) and pyrrolidine-substituted perylene diimide (PN) in DNA and rapid electron transfer in these complexes, which has been analyzed by steady-state fluorescence and femtosecond transient absorption measurements, have been demonstrated. The DNA molecules possessing PH and PN were prepared through a recently developed method that involved the reaction of enzymatically generated abasic sites with the amino groups of the perylene diimide molecules, through which these molecules can be incorporated as base surrogates within the DNA base stack. Melting temperature analysis showed that the PH and PN monomers, and their homo- and heterodimers, contribute to the stabilization of the DNA duplex, and is comparable to that of natural base pairs. Fluorescence measurements showed that PH in a single-stranded oligopyrimidine showed a strong fluorescence, whereas the fluorescence of PH was completely quenched upon pairing with PN (PH/PN) through duplex formation. The transient absorption measurements showed that a rapid electron-transfer reaction in the stacked PH/PN heterodimer occurred on a sub-picosecond timescale, which allowed highly efficient fluorescence quenching. The PH/PN pair, which served as a fluorophore and quencher, were utilized to design molecular beacon probes with a high signal/noise ratio. The PH/PN pair was also capable of forming a stable, stacked dimer structure and induced rapid electron transfer that could serve as a good signal reporter for fluorescent nucleic acid detection.

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“…In a DNA scaffold, an alternating fashion were arranged by pyrene and perylenediimide (PDI) molecules. The observation of electronic coupling between chromophores of the same type in alternating arrangements indicated that the pyrene H-aggregates and PDI co-exist in p-stacked hetero-aggregates [38]. …”

Section: Small Molecules Modified Dnamentioning

confidence: 99%

Amphiphilic DNA Organic Hybrids: Functional Materials in Nanoscience and Potential Application in Biomedicine

Zhao

Liang

et al. 2018

IJMS

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Due to the addressability and programmability, DNA has been applied not merely in constructing static elegant nanostructures such as two dimensional and three dimensional DNA nanostructures but also in designing dynamic nanodevices. Moreover, DNA could combine with hydrophobic organic molecules to be a new amphiphilic building block and then self-assemble into nanomaterials. Of particular note, a recent state-of-the-art research has turned our attention to the amphiphilic DNA organic hybrids including small molecule modified DNA (lipid-DNA, fluorescent molecule-DNA, etc.), DNA block copolymers, and DNA-dendron hybrids. This review focuses mainly on the development of their self-assembly behavior and their potential application in nanomaterial and biomedicine. The potential challenges regarding of the amphiphilic DNA organic hybrids are also briefly discussed, aiming to advance their practical applications in nanoscience and biomedicine.

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Formation of Two Homo‐chromophoric H‐Aggregates in DNA‐Assembled Alternating Dye Stacks

Cited by 52 publications

References 39 publications

Light‐Harvesting Nanotubes Formed by Supramolecular Assembly of Aromatic Oligophosphates

Light‐Harvesting Nanotubes Formed by Supramolecular Assembly of Aromatic Oligophosphates

Rapid Electron Transfer of Stacked Heterodimers of Perylene Diimide Derivatives in a DNA Duplex

Amphiphilic DNA Organic Hybrids: Functional Materials in Nanoscience and Potential Application in Biomedicine

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