Alternating DNA and π-Conjugated Sequences. Thermophilic Foldable Polymers

Wang, Wei; Wan, Wei; Zhou, Hanhan; Niu, Shuqiang; Li, Alexander D. Q.

doi:10.1021/ja0341900

Cited by 159 publications

(153 citation statements)

References 27 publications

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“…The formation of this new band in the emission spectrum of PBIs has been extensively discussed in the literature. According to Wang et al 35,[76][77][78] who examined the self-organization of a PEG functionalized PBI in chloroform solution, such a red shifted band in the emission spectrum of PBIs may be attributed to the fluorescence properties of molecular assemblies of increased size. The same conclusions have also been outlined by Neuteboom and coworkers 79 when studying the optical features of polytetrahydrofuran substituted PBI polymers in ODCB.…”

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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“…[10][11][12][13] Furthermore, the ''base-by-base'' synthesis of oligonucleotides makes it possible to control both their length and their sequence from a few to more than one hundred bases. Besides base modification [14] or the incorporation of p-conjugated oligomers into the DNA backbone by covalent linking, [15][16][17] the use of the H-bonding recognition process in the design of (single-strand) oligonucleotide-chromophore conjugates also appears as an interesting path to prepare monodisperse aggregates. [18,19] This approach offers a major advantage: by exploiting the base recognition process, it would be possible to control the sequence of different functional units along the single-strand DNA (ssDNA).…”

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confidence: 99%

Supramolecular Organization of ssDNA‐Templated π‐Conjugated Oligomers via Hydrogen Bonding

et al. 2009

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The templated self‐assembly of water‐soluble π‐conjugated molecules bearing a diaminotriazine moiety H‐bonding to a single‐strand oligothymine template leads to defined structures. We study these assemblies with molecular modeling, circular dichroism spectroscopy, and scanning probe microscopy, to get a better understanding of the factors governing the supramolecular organization and structural order.

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“…This band corresponds to the excimer-type emission of the PB dimer that has been observed in nanoaggregates of perylene bisimides. [3,8,15] The UV/Vis spectra of DNA1 and DNA3 (Figure 2) at low temperatures show two major bands that are hyposochromically (506 nm) or bathochromically (545 nm) shifted in comparison to the 0!1 and 0!0 vibronic transitions of the PB monomer.[16] This result shows the strong p-p excitonic interactions of the two PB chromophores inside (DNA1) and outside (DNA3) of the duplex. [15] Both the excimer-type fluorescence band and the shifted absorption bands of DNA1 vanish at higher temperatures.…”

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Perylene Bisimide Dimers as Fluorescent “Glue” for DNA and for Base‐Mismatch Detection

2008

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Perylene-3,4:9,10-tetracarboxylic acid bisimide ("PB") and its derivatives are applied as fluorescent dyes in organic materials owing to their excellent photochemical stability as well as the high fluorescence quantum yields. [1,2] The strong hydrophobic stacking interactions between the PB chromophores make this dye an important building block for functional supramolecular architectures. [1,3] Based on these properties, PB in the dimeric form should be also of potential interest as a probe for fluorescent DNA/RNA analytics as well as for functionalized DNA-based architectures. Its noncovalent DNA-binding interactions have been studied with PB derivatives that had been modified with spermine [4] or other amines.[5] Moreover, an increasing number of publications about covalent modifications of oligonucleotides with PB have appeared over the last few years. [6][7][8][9][10][11][12] Recently, we presented a facile route for the synthetic incorporation of PB as an artificial DNA base in order to study the stacking interactions of this dye at specific sites in duplex DNA.[13]Herein, we present the evaluation of fluorescent PB dimers for the optical functionalization of DNA using three representative duplexes (DNA1, DNA3, and DNA4 a). For the synthetic modification of the corresponding oligonucleotides with the PB chromophore (Scheme 1), the 2-deoxyribofuranoside moiety was replaced by an acyclic linker system which is tethered to one of the imide nitrogens of the PB dye.[13] This linker allows the chromophore to intercalate in the base stack while providing high chemical stability during the automated phosphoramidite chemistry. [13,14] DNA1 bears one interstrand PB dimer inside the duplex, whereas DNA3 contains a PB monomer outside the duplex at each 5' end. Both duplexes contain palindromic sequences. When DNA1 and DNA3 are excited at 505 nm, the fluorescence spectra of both duplexes (Figure 1) are dominated by a broad band at % 660 nm without fine structure. This band corresponds to the excimer-type emission of the PB dimer that has been observed in nanoaggregates of perylene bisimides. [3,8,15] The UV/Vis spectra of DNA1 and DNA3 (Figure 2) at low temperatures show two major bands that are hyposochromically (506 nm) or bathochromically (545 nm) shifted in comparison to the 0!1 and 0!0 vibronic transitions of the PB monomer.[16] This result shows the strong p-p excitonic interactions of the two PB chromophores inside (DNA1) and outside (DNA3) of the duplex. [15] Both the excimer-type fluorescence band and the shifted absorption bands of DNA1 vanish at higher temperatures. It is remarkable that this occurs cooperatively at a temperature (75.9 8C) that corresponds to the cooperative thermal dehybridization of the whole DNA duplex, which is typically measured at 260 nm (T m = 78.6 8C). Apparently the intact helical duplex is required as a framework for the PB dimer formation. In comparison to the unmodified DNA2 (T m = 76.2 8C) the duplex DNA1 is stabilized by 2.4 8C through the Scheme 1. PB-modified duplexes DNA1-DNA3...

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Alternating DNA and π-Conjugated Sequences. Thermophilic Foldable Polymers

Cited by 159 publications

References 27 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

Supramolecular Organization of ssDNA‐Templated π‐Conjugated Oligomers via Hydrogen Bonding

Perylene Bisimide Dimers as Fluorescent “Glue” for DNA and for Base‐Mismatch Detection

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