Packing-induced solid-state fluorescence and thermochromic behavior of peptidic luminophores

Pramanik, Apurba; Haldar, Debasish

doi:10.1039/c6ra24799g

Cited by 9 publications

(6 citation statements)

References 38 publications

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“…All the luminophores (Figure 1) were synthesized following standard solution phase methodologies, purified, and characterized by 1 H NMR, 13 C NMR, and Mass spectrometry analysis. All the imine compounds were synthesized using aminocoumarin compound 5 as a precursor [41] . The benzaldehyde, o ‐hydroxy benzaldehyde, p ‐hydroxy benzaldehyde, and m ‐hydroxy benzaldehyde were commercially available.…”

Section: Resultsmentioning

confidence: 99%

“…The aminocoumarin 5 was synthesized following the reported procedure [41] . The compound 5 was taken in a 100 mL flask and dissolved in 30 mL absolute ethanol.…”

Section: Methodsmentioning

confidence: 99%

“…Ting and co‐workers have exploited the coumarin ligation technique for imaging protein‐protein interactions inside a living cell [37] . Recently there have been several reports on solid‐state optical properties of coumarin‐based fluorophores [38–41] . So far, few coumarin‐based compounds have been known to exhibit fluorescence in solid‐state.…”

Section: Introductionmentioning

confidence: 99%

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Topology‐Controlled AIEE of Iminocoumarin Luminophores

Chattapadhyay

Mondal

Kumar

et al. 2021

Chemistry An Asian Journal

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Aggregation‐induced emission enhancement (AIEE) is an unusual phenomenon where luminophores show a higher photoluminescence efficiency in the aggregated and solid state. We report the design and synthesis of a series of luminophores 1–4 with imine functionality at 6 position of coumarin and studied their AIE propensities on self‐assembly. The effect of the topology of the phenolic hydroxyl group on the emission behaviour of the luminophores has been investigated. The imines show significant solvatochromism with high emission in non‐polar solvents, whereas the emission gets quenched in the polar solvent. The fluorescence in the toluene‐hexane mixture arises due to the aggregation of fluorophores and falls under the category of AIEE. Not only the solution state emission of the isomeric iminocoumarin luminophores is notably varied, but also their solid‐state emission found to be significantly different from each other. Moreover, the iminocoumarin 1 selectively recognizes Fe(III) over Fe(II) with a prominent color change. In situ oxidation of Fe(II) with H2O2 exhibits the same effect like Fe(III) and developed a chemical combinational logic gate.

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Section: Resultsmentioning

confidence: 99%

“…The aminocoumarin 5 was synthesized following the reported procedure [41] . The compound 5 was taken in a 100 mL flask and dissolved in 30 mL absolute ethanol.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Topology‐Controlled AIEE of Iminocoumarin Luminophores

Chattapadhyay

Mondal

Kumar

et al. 2021

Chemistry An Asian Journal

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“…In recent years short peptide based porous materials are a new entry in this family. Low production cost, biocompatibility, control over structural reversibility and their straightforward chemical synthesis render peptides wonderful platform for biomaterial design . The torsions available in the polypeptide chain often enables peptides an adaptable response to the environment from group of low‐lying and kinetically accessible states.…”

Section: Introductionmentioning

confidence: 99%

Porous Biomaterials via Side Chain‐Side Chain Interactions of Tyrosine Analogue of Pyridine Carboxamides

et al. 2018

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Peptide based porous materials have attracted recent attention due to their environmentally benign nature. In an attempt to artificially imitate their importance, we have synthesized a set of three pseudopeptides comprising of a single pyridinedicarboxylic acid and a flexible dipeptidyl fragment H-Xaa-Yaa-OMe (Xaa: L-Ala, Yaa: mABA, pseudopeptide I ; Xaa: L-Tyr, Yaa : mABA, pseudopeptide II; Xaa: L-Ile, Yaa : Tyr, pseudopeptide III, mABA: meta amino benzoic acid ) using Boc chemistry. Our experimental analysis using X-ray crystallography illustrates that pseudopeptide I-III displays supramolecular preference for double helices, characterestic of pyridine carboxamides, employing intermolecular H-bonding and p-p analogy. To date, literature documentation reveals that the reported double helical motifs have been modulated either by utilizing DNA conjugates or rigid templates, mainly governed by the concept of backbone-backbone interaction. However, to the best of our knowledge these novel examples represent one of the very few reports of the architectural design solely nucleated by ecofriendly amino acids driven by sidechain -sidechain correspondence, exhibiting significant difference in self-assembling properties. Our UV/Visible, concentration dependant NMR experiment and Circular Dichroism measurement complies with the solid state conformational analysis. Interestingly, the double helical ensemble of pseudopeptide II (Tyr analogue bearing additional H-bonding ability of phenolic OH) unveil fifteen times more N 2 sorption (65 cc/g) than pseudopeptide I (Ala, devoid of additional H-bonding ability) (4.5 cc/g), furthermore emphasizing the dominant role of side chain -side chain interaction in porous biomaterial design. Besides our findings also spotlights the relevance of positional displacement of TyrmABA fragment in controlling gas adsorption properties (pseudopeptide III; 5 cc/g). Our morphological analysis using FE-SEM inaddition supports our experimental observation.

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“…Peptides meet all the requirements necessary for the heirarchical process as they are composed of ecofriendly amino acids. Moreover their versatile synthesis strategy, biocompatibility and bioactivity makes them wonderful motifs for biomaterial design …”

Section: Introductionmentioning

confidence: 99%

Proteolysis‐Resistant Self‐Assembled ω‐Amino Acid Dipeptide‐Based Biocompatible Hydrogels as Drug Delivery Vehicle

et al. 2017

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In this report we demonstrate the excellent hydrogelating ability of two Fluorenylmethoxycarbonyl (Fmoc) protected dipeptides, Fmoc-Xaa-Phe-OH (Xaa, Gaba, Hydrogelator I; Xaa, Ava, Hydrogelator II; Gaba = g -aminobutyric acid; Ava = d-Amino Valeric acid) with w-amino acids exhibiting conformational flexibility. Since Proteolysis is the disadvantage for peptide-based therapeutic agents, our design includes dipeptides known to show resistance towards proteolysis. The gelation property of the hydrogels were characterized by various analysis. It was concluded that the hydrogels were non cytotoxic in four completely different cell lines, which indicates its biocompatibility. These biomaterials were used to stabilize nanoparticles (HNPs) using the concept of self-assembly, utilizing weak interactions rather than extreme conditions as seen in other polymers. These hydrogelators have shown good entrapment efficiency and release kinetics of the model drug curcumin from the hydrogel matrix. Our investigation reveals that hydrogelator II has an enhanced release profile due to the presence of methylene groups in the peptide backbone. This hypothesis is also supported by our computational studies.Thus our research holds future promise for using these biomaterials as vehicles for drug delivery.

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Packing-induced solid-state fluorescence and thermochromic behavior of peptidic luminophores

Cited by 9 publications

References 38 publications

Topology‐Controlled AIEE of Iminocoumarin Luminophores

Topology‐Controlled AIEE of Iminocoumarin Luminophores

Porous Biomaterials via Side Chain‐Side Chain Interactions of Tyrosine Analogue of Pyridine Carboxamides

Proteolysis‐Resistant Self‐Assembled ω‐Amino Acid Dipeptide‐Based Biocompatible Hydrogels as Drug Delivery Vehicle

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