Synthesis of phthalimide disperse dyes and study on the interaction energy

Yi-zhen, Zhan; Zhao, Xue; Wang, Wei

doi:10.1016/j.dyepig.2017.07.013

Cited by 24 publications

(15 citation statements)

References 19 publications

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“…Therefore, it is thought that T sm should be near or slightly higher than the T g of the polymer of the fabric to be surface-modified. The anchoring of the ANT parts diffused inside the fibers occurs in the next two stages C and D. In stage C (Anchoring I), the ANT parts that are already diffused into the PET fibers poke through and anchor to the fiber at T sm via physical interactions including hydrophobic, dipole–dipole, and π–π interactions . When the temperature cools down to room temperature, the ANT parts more tightly anchor to the PET fiber via mechanical locking caused by no mobility of PET chains and also by obstructing the SMAs to escape from the fibers (stage D: Anchoring II).…”

Section: Resultsmentioning

confidence: 99%

New Surface Modification Method To Develop a PET-Based Membrane with Enhanced Ion Permeability and Organic Fouling Resistance for Efficient Production of Marine Microalgae

Kim

Lee

Park

et al. 2020

ACS Appl. Mater. Interfaces

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This paper presents a new surface modification strategy to develop a poly(ethylene terephthalate) (PET)-based membrane having a hydrophilic surface, high nutrient ion permeability, sufficient mechanical strength, and organic fouling resistance, using an anthracene (ANT)-attached polyethylene glycol (PEG) surface modification agent (SMA) synthesized in this work. During the modification process, the ANT parts of the SMAs poke through and anchor to the surface of a commercial PET woven fabric via physical interactions and mechanical locking. The PEG chain parts coat the surface in the brush and arch forms, which generates a hydration layer on the fabric surface. The consequently obtained surface property and unique structure of the modified PET-based membrane result in higher nitrate ion permeability, organic fouling resistance, and microalgae production compared to those of the unmodified one. These are also affected by the molecular weight of the PEG and the number density of the anchored SMAs. The study demonstrates that this new surface modification method has the potential to allow the development of a desirable PET-based membrane for the efficient massive production of marine microalgae.

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Section: Resultsmentioning

confidence: 99%

New Surface Modification Method To Develop a PET-Based Membrane with Enhanced Ion Permeability and Organic Fouling Resistance for Efficient Production of Marine Microalgae

Kim

Lee

Park

et al. 2020

ACS Appl. Mater. Interfaces

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“…The synthetic pathway of the compounds is presented in Scheme 1. To synthesize 1 (4-nitrophthalimide), 2 (4-nitro-N-ethylphtalimide) and 3 (4-amino-N-ethylphthalimide), we have followed the methodology of previously published papers [44,45]. The 1 H and 13 C NMR spectra of 3 used as an intermediate compound to synthesize 2-hydroxy-Schiff bases are presented in the Supporting information.…”

Section: Synthesismentioning

confidence: 99%

“…Two 4-substituted phthalimide 2-hydroxy-Schiff bases containing salicylic and 2-hydroxy-1-naphthyl moieties, respectively, were synthesized via a four steps synthetic procedure (Scheme 1). A classical nitration of phthalimide to 4-nitrophthalimide (1) was performed as a first step, followed by a nucleophilic substitution of NH imide by ethyl bromide in DMF in the presence of K 2 CO 3 to N-ethyl-4-nitrophthalimide (2) [44]. The ethyl group was introduced in order to increases the solubility and to avoid NH deprotonation.…”

Section: Ground State Tautomerismmentioning

confidence: 99%

Indirect solvent assisted tautomerism in 4-substituted phthalimide 2-hydroxy-Schiff bases

Yordanov

Deneva

Georgiev

et al. 2020

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The paper presents the synthesis and characterization of two 4-substituted phthalimide 2-hydroxy-Schiff bases containing salicylic (4) and 2-hydroxy-1-naphthyl (5) moieties. The structural differences of 2-hydroxyaryl substituents, resulting in different enol/keto tautomeric behaviour, depending on the solvent environment were studied by absorption UV-Vis spectroscopy. Compound 5 is characterized by a solvent-dependent tautomeric equilibrium (K T in toluene = 0.12, acetonitrile = 0.22 and MeOH = 0.63) while no tautomerism is observed in 4. Ground state theoretical DFT calculations by using continuum solvation in MeOH indicate an energy barrier between enol/keto tautomer 5.6 kcal mol −1 of 4 and 0.63 kcal mol −1 of 5, which confirms the experimentally observed impossibility of the tautomeric equilibrium in the former. The experimentally observed specific solvent effect in methanol is modeled via explicit solvation. The excited state intramolecular proton transfer (ESIPT) was investigated by steady state fluorescence spectroscopy. Both compounds show a high rate of photoconversion to keto tautomers hence keto emissions with large Stokes shifts in five alcohols (MeOH, EtOH, 1-propanol, 1-butanol, and 1-pentanol) and various aprotic solvents (toluene, dichlormethane, acetone, AcCN). According to the excited state TDDFT calculations using implicit solvation in MeOH, it was found that enol tautomers of 4 and 5 are higher in energy compared to the keto ones, which explains the origin of the experimentally observed keto form emission.

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“…Thus, it was hardly used in dyeing fabrics. Fortunately, there are some different ways to improve the photo-stability of the dyes, for example improving the photo-stability of dyes using TiO 2 [19], while computational chemistry could estimate behaviors of dyes under light according to quantum chemistry, which could provide theoretical speculations of photo-chemical/light fastness of the dyes [20,21,22,23,24,25].…”

Section: Introductionmentioning

confidence: 99%

Computer-Assisted Design of Environmentally Friendly and Light-Stable Fluorescent Dyes for Textile Applications

Tang

Chen

Sun

2019

IJMS

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Five potentially environmentally friendly and light-stable hemicyanine dyes were designed based on integrated consideration of photo, environmental, and computational chemistry as well as textile applications. Two of them were synthesized and applied in dyeing polyacrylonitrile (PAN), cotton, and nylon fabrics, and demonstrated the desired properties speculated by the programs. The computer-assisted analytical processes includes estimation of the maximum absorption and emission wavelengths, aquatic environmental toxicity, affinity to fibers, and photo-stability. This procedure could effectively narrow down discovery of new potential dye structures, greatly reduce and prevent complex and expensive preparation processes, and significantly improve the development efficiency of novel environmentally friendly dyes.

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Synthesis of phthalimide disperse dyes and study on the interaction energy

Cited by 24 publications

References 19 publications

New Surface Modification Method To Develop a PET-Based Membrane with Enhanced Ion Permeability and Organic Fouling Resistance for Efficient Production of Marine Microalgae

New Surface Modification Method To Develop a PET-Based Membrane with Enhanced Ion Permeability and Organic Fouling Resistance for Efficient Production of Marine Microalgae

Indirect solvent assisted tautomerism in 4-substituted phthalimide 2-hydroxy-Schiff bases

Computer-Assisted Design of Environmentally Friendly and Light-Stable Fluorescent Dyes for Textile Applications

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