Water-soluble naphthalene diimides: synthesis, optical properties, and colorimetric detection of biogenic amines

Weißenstein, Annike; Grande, Vincenzo; Saha‐Möller, Chantu R.; Würthner, Frank

doi:10.1039/c8qo00611c

Cited by 19 publications

(17 citation statements)

References 60 publications

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“…Polynucleotides poly(dA-dT) 2 , poly(AU), calf thymus (ct)-DNA, and poly(dG-dC) 2 were obtained from Sigma-Aldrich. The starting compound 1 was prepared according to the literature [31]. Column chromatography was performed on silica gel (MerckSilica 60, particle size 0.04-0.063 mm).…”

Section: Methodsmentioning

confidence: 99%

“…Based on the design concept discussed above, the NDIs 3a,b and 5 were obtained in three synthetic steps according to Scheme 1, starting from the literature-known dichloro NDI 1 having two 3-dimethylaminopropyl groups attached to the imide nitrogens [31]. This compound was first methylated at the nitrogen atoms by the reaction with iodomethane in refluxing toluene, giving the diammonium NDI 2 in a very good yield of 89%.…”

Section: Synthesismentioning

confidence: 99%

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Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

Weißenstein¹,

Vysotsky²,

Piantanida³

et al. 2020

Beilstein J. Org. Chem.

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Two novel unnatural amino acids, prepared by linking a dicationic purple-coloured and fluorescent naphthalene diimide (NDI) at core position to amino acid side chains of variable length, strongly interacted with ds-DNA/RNA by threading intercalation. Different from a reference NDI dye with identical visible range absorbance (520–540 nm) and Stokes shifts in emission (+60 nm, quantum yield > 0.2), only these amino acid–NDI conjugates showed selective fluorimetric response for GC-DNA in respect to AT(U)-polynucleotides. The DNA/RNA binding-induced circular dichroism (ICD) response of NDI at 450–550 nm strongly depended on the length and rigidity of the linker to the amino acid unit, which controls the orientation of the NDI unit inside within the intercalative binding site. The ICD selectivity also depends on the type of polynucleotide, thus the studied NDI dyes act as dual fluorimetric/ICD probes for sensing the difference between here used GC-DNA, AT-DNA and AU-RNA.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

Weißenstein¹,

Vysotsky²,

Piantanida³

et al. 2020

Beilstein J. Org. Chem.

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“…al. 23 and Doria et. al., 24 which is in contrast to our method of using base to deprotonate amino acid side chains to make water soluble NDIs.…”

Section: Introductionmentioning

confidence: 93%

“…25 This band is the result of the isopropyl amino substituents raising the HOMO energy level of the material and is commonly observed in other NDIs with similar core substituents. 23,25,34 As such, it is not present in the unfunctionalised analogue which displays little to no absorption above 400 nm. The a)…”

Section: Electronic and Optical Characterisationmentioning

confidence: 99%

“…[19][20][21][22] One such functionalisation is the incorporation of amino groups off the core which has been shown to provide NDIs with exceptional photophysical properties including a deep blue colour. [22][23][24][25][26] The synthesis can also be done under mild conditions without the need for coreagents or transition metal catalysts. 26 Some of these materials have even been made water soluble.…”

Section: Introductionmentioning

confidence: 99%

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Electronic and assembly properties of a water-soluble blue naphthalene diimide

et al. 2021

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Isothermal Phase Transitions in Liquid Crystals Driven by Dynamic Covalent Chemistry

Martínez,

Schlossarek,

Würthner

et al. 2024

Angewandte Chemie

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The dynamic nature of calamitic liquid crystals is exploited to perform isothermal phase transitions driven by dynamic covalent chemistry. For this purpose, nematic (N) arrays based on aldehyde 1 were treated with different amines (A‐E) in an on‐surface process, which resulted in different isothermal phase transitions. These phase transformations were caused by in‐situ imination reactions and are dependent on the nature of the added amine. Transitions from the N to crystal (1A, 1E), isotropic (1B), and smectic (Sm) (1C, 1D) phases were achieved, while the resulting materials feature thermotropic liquid crystal behavior. A sequential transformation from the N 1 to the Sm 1C and then to the N 1B was achieved by coupling an imination to a transimination processes and adjusting the temperature. All of these processes were well characterized by microscopic, spectroscopic, and X‐ray techniques, unlocking not only the constitutional but also the structural aspects of the phase transitions. This work provides new insights into designing constitutionally and structurally adaptable liquid crystal systems, paving the way toward the conception of programable evolutive pathways and adaptive materials.

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Water-soluble naphthalene diimides: synthesis, optical properties, and colorimetric detection of biogenic amines

Abstract: Biocompatible water-soluble naphthalene diimides (NDIs) were synthesized and a core-dichlorinated NDI was shown to detect primary amines and biogenic diamines.

Cited by 19 publications

References 60 publications

Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

Electronic and assembly properties of a water-soluble blue naphthalene diimide

Isothermal Phase Transitions in Liquid Crystals Driven by Dynamic Covalent Chemistry

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