Assemblies of perylene diimide derivatives with melamine into luminescent hydrogels

Sukul, Pradip K.; Asthana, Deepak; Mukhopadhyay, Pritam; Summa, Domenico; Muccioli, Luca; Zannoni, Claudio; Beljonne, David; Rowan, Alan E.; Malik, Sudip

doi:10.1039/c1cc14189a

Cited by 76 publications

(65 citation statements)

References 23 publications

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“…In related work, we reported a fluorescence application of new chiral thiazole‐based melamine derivatives exhibiting different chiral recognition abilities toward the enantiomers of various carboxylic acids . Thus, we initiated our study with the synthesis of thiazole‐based triazine skeleton 3 .…”

Section: Resultsmentioning

confidence: 99%

“…In related work, we reported a fluorescence application of new chiral thiazole-based melamine derivatives exhibiting different chiral recognition abilities toward the enantiomers of various carboxylic acids. [43][44][45][46][47][48][49] Thus, we initiated our study with the synthesis of thiazole-based triazine skeleton 3. According to the synthetic route in Scheme 1, in the presence of diisopropylethylamine (DIPEA), triazine 1 reacted with 1.1 equiv of 2-(2aminophenyl)benzothiazole 2 in THF.…”

Section: Synthesis and Aie Properties Of New Chiral Thiazole Derivamentioning

confidence: 99%

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Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Halay

Bozkurt

2017

Chirality

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Hydrogen bonding and π-π interactions take special part in the enantioselectivity task. In this regard, because of having both hydrogen acceptor and hydrogen donor groups, melamine derivatives become more of an issue for enantioselectivity. In the light of such information, triazine-based chiral, fluorescence active novel thiazole derivatives L1 and L2 were designed and synthesized from (S)-(-)-2-amino-1-butanol and (1S,2R)-(+)-2-amino-1,2-diphenylethanol. The structural establishment of these compounds was made by spectroscopic methods such as FTIR, H, and C NMR. While the solution of these compounds in DMSO did not show any fluorescence emission, it was observed that the emission increased 44-fold for L1 and 55-fold for L2 in 95% water, similar to the aggregation-induced emission (AIE) characterized compounds. In this regard, enantioselective capabilities of these compounds against carboxylic acids were tested, and in experiments carried out at a ratio of 40/60 DMSO/H O, it was determined that R-2ClMA increased the fluorescence emission of L1 chiral receptor by 2.59 times compared to S-isomer.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis and Aie Properties Of New Chiral Thiazole Derivamentioning

confidence: 99%

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Halay

Bozkurt

2017

Chirality

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“…In recent years, many functional nanomaterials have been synthesized through the use of self-assembly. The driving forces for self-assembly include non-covalent interaction forces, such as π-π interactions, hydrogen bonding, hydrophilic/hydrophobic interactions, van der Waals forces and charge interaction forces [1][2][3][4]. π-Conjugated systems have attracted great attention for applications to self-assembly mainly because of their designable molecular structures and excellent optoelectronic properties.…”

Section: Introductionmentioning

confidence: 99%

Organic Acid Regulated Self-Assembly and Photophysical Properties of Perylene Bisimide Derivatives

Wang

Yang

et al. 2020

Materials

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In this work, perylene bisimide derivatives (PBI-1 and PBI-2) with tertiary amine groups were designed and synthesized. To control the final morphologies and properties of their aggregates, seven kinds of organic acids were used to alter the self-assembly environment. The influence of organic acids on the morphology of the aggregates was investigated. Photophysical properties of the aggregates were markedly affected by the kind and concentration of the organic acid. The thermal and gas sensitivities of the PBI-1 aggregates were studied with the use of UV–visible spectroscopy and digital imaging. The shift of the UV–visible spectra varied with time, temperature, acid type and acid concentration. Furthermore, PBI-1 aggregates showed a red-to-blue color change after addition of seven organic acids, whereas the color of the PBI-2 aggregates remained red. These changes of morphologies, photophysical properties and their thermal and gas sensitivities make these aggregates potentially useful in the fields of optoelectronics or sensors.

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“…Supramolecular gels based on low‐molecular‐mass organogelators (LMOGs) have attracted significant attention over the past few decades, largely driven by their broad range of potential applications, including drug delivery, templated reactions, materials and devices, molecular sensing, and oil‐spill recovery . Recently, phase‐selective gelators (PSGs), which preferentially gelate one solvent over others from a given mixture at room temperature, have also been reported .…”

Section: Introductionmentioning

confidence: 99%

A Smart Phase‐Selective Gelator for Recycling Aromatic Solvents, the Removal of Toxic Dyes, and Molecular Delivery

Ran

Gao

et al. 2016

Asian J Org Chem

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The phase-selectiveg elation properties of al owmolecular-mass organogelator, N-(3,4,5-tributoxyphenyl)-N'-4-[(4-hydroxyphenyl)azophenyl] benzohydrazide (BNB-t4), and its applications in recycling aromatic solvents, removing toxic dyes, andm olecular delivery,a re reported. The hydroxy head group, hydrazide group, and three butyl chains in this compound provide the collective driving force for self-assembly and make BNB-t4 an excellent phase-selective gelator (PSG). FTIR and UV/Vis spectroscopy suggest that the driving forces for the gelation are hydrogen-bonding, p-p stacking and Vand er Waals interactions. The criticalg elation concentration (CGC) of BNB-t4 in aromatics olvents is very low (e.g.,0 .6 mg mL À1 in toluene), which suggests that the BNB-t4 PSG could extract aromatic solvents from aqueous mixtures. Our resultsi ndicatet hat the entangled fibrousn etwork and its rheological properties enable BNB-t4 to function as ar eversible materialf or removing toxic dyes from aqueous solution with efficiencies as high as 97 %. Furthermore, its combined phase-selectiona nd reversible phasetransition properties conferB NB-t4 the ability to absorba nd releaseo rganic compounds with efficiencies of up to 98 %. Ta ken together,t hese results demonstrate that BNB-t4c ould be used to construct smart materials for environment remediation and molecular delivery.Scheme1.Molecular structure of BNB-t4.[a] Dr. Figure 11. Absorptionspectra of water contaminated with RhB dye on alternating the temperature from 85 8CtoRTto858Cf or five cycles.

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Assemblies of perylene diimide derivatives with melamine into luminescent hydrogels

Cited by 76 publications

References 23 publications

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Organic Acid Regulated Self-Assembly and Photophysical Properties of Perylene Bisimide Derivatives

A Smart Phase‐Selective Gelator for Recycling Aromatic Solvents, the Removal of Toxic Dyes, and Molecular Delivery

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