Effect of increasing methoxyphenyl substitution on pyrene pyrazoline enduring green light emitting materials

Karuppusamy, A.; Arulkumar, R.; Kannan, P.; Venuvanalingam, Ponnambalam

doi:10.1016/j.jphotochem.2019.04.003

Cited by 13 publications

(4 citation statements)

References 65 publications

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“…In addition, increasing the amount of 4 a also facilitated the reaction (Table 1, entries 14-15). The effects of several additives were also tested in the reaction (Table 1, entries [16][17][18][19][20][21][22]. It was found that benzoic acid could efficiently promote the reaction and 87 % yield was finally obtained when 2.0 equiv.…”

Section: Resultsmentioning

confidence: 99%

“…[7][8][9][10] They have undoubtedly promoted high-tech innovations in numerous aspects, such as organic light-emitting diodes (OLEDs), [11] biological probes, [12] chemical sensing, [13][14] clinical diagnosis, [15][16][17][18] and so on. In recent years, green [19][20][21] and blue emitters [22][23][24] have also been developed, which have been widely employed in optoelectronic devices because of their high luminance, high efficiency, and long lifetimes. [25] Meanwhile, red-emitting materials are not only important dopants for the fabrication of flexible devices and biological imaging, but also have low interference from biological background signals, powerful tissue penetration, and less scattering interference.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Piperidine‐based Derivatives as Red Emitting Lu‐minescent Materials

Wang,

Guo,

2024

ChemPhotoChem

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Organic fluorescent materials have become increasingly attractive due to the requirements of green chemistry. In this study, the synthetic route of piperidine‐based fluorescent materials was optimized with good to excellent yields. 37 fluorescent compounds were achieved with emission wavelength at 540‐670 nm and chromogenic changed from green to standard red. The fluorescence quantum yields of 5a, 5ab, and 5af were 1.96%, 0.97%, and 5.13%, respectively. The relationship between the structure and luminescent properties has also been systematically discussed. This work presents the possibility of utilizing piperidine analogues to develop fluorescent probes in biological imaging, display devices and other related fields.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Piperidine‐based Derivatives as Red Emitting Lu‐minescent Materials

Wang,

Guo,

2024

ChemPhotoChem

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“…Pyrazolines were well known for their pharmacological properties, and also, the presence of many hetero atoms in the molecule induces excellent blue fluorescence. These emission properties were used in dye-sensitized based solar cells, optical emitting, hole transfer materials [21][22][23][24], etc.…”

Section: Introductionmentioning

confidence: 99%

A Review on Metal Ion Sensors Derived from Chalcone Precursor

2022

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Disclosure of new molecular probes as chromogenic and fluorogenic cation sensors is scientifically exigent work. Recently chalcone derivatives gained more attention because of their structural variability. A suitable donor and acceptor groups separated by delocalized π-orbitals display excellent chromogenic and fluorogenic properties because of intramolecular charge transfer (ICT). These designed molecular frameworks provide the coordination sites to the incoming metal ions results in small changes in the optical properties. In a typical sensing behavior, coordination leads to a large conjugation plane with the probe resulted in hypo/hyperchromic shifts or red/blue shifts. In this review, we tried to converge the reported chalcone-derived sensors and explored the design, synthesis, metal ion sensing mechanism, and practical application of the probes. We expect that this review gives a basic outline for researchers to explore the field of chalcone-based sensors further.

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“…The crude product, therefore obtained, was filtered and dried in a vacuum for 8 h, the resultant pyrazoline materials were purified using column chromatography (chloroform:hexane 1:4). [30][31][32][33][34][35] The prepared PPT, PPF, and PPP were systematically characterized and reported and their molecular structures (Scheme 1) were confirmed using 1 H-NMR (Figures S1-S3) and mass spectrometry (Figures S4-S6).…”

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confidence: 98%

Twisted intramolecular motion arrested in aggregated state emission and the nonlinear optical properties of pyrene pyrazoline derivatives

et al. 2021

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Heterocyclic pyrene pyrazoline moieties containing similar structures but with differences in thiophene (PPT), furan (PPF) and pyridine (PPP) substitutions at the terminal molecules were synthesized. Their aggregation behaviour in THF-water mixtures was investigated and results demonstrated that PPT and PPP exhibited aggregationinduced emission (AIE), whereas PPF exhibited aggregation-induced blue-shifted emission (AIBSE). PPT and PPP provided red-shifted emission, while PPF had observed blue-shifted emission at high water fractions of 70-90%, confirming that aggregation effects played a major role in the molecular structure. Two emission peaks from locally excited and twisted intramolecular charge transfer confirmed the twisted nature from the dihedral angle values of the free reorganized molecules that were completely restricted in high water fractions due to molecular aggregation. This was further confirmed from colour Commission Internationale de l'Eclairage values as well as dynamic light scattering analysis. Third-order nonlinear optical properties were studied using a Nd:Yag laser beam Z-scan technique at 532 nm. The open aperture Z-scan revealed that PPT and PPF towards the peak point endured strong saturable absorption, whereas PPP indicated a strong reverse saturable absorption process. The AIE and AIBSE mechanisms from undergoing restricted twisting intramolecular motion in the aggregated luminogens provide great insight into new developments in AIEgen materials for these optoelectronic materials. K E Y W O R D Saggregation-induced blue-shifted emission, aggregation-induced emission, arylpyrazolines, nonlinear optical materials, organic optoelectronics | INTRODUCTIONFluorescent organic small molecules have received significant attention in modern technology for their vital application in various research areas such as organic light-emitting diodes, [1] organic lasers, [2] organic field effect transistors, [3] organic dye solar cells, [4] organic ligands for detection of hazardous metal ions, [5,6] fluorescent probes [7] and bio-imaging. [8,9] Conventional organic luminophores have drawbacks of molecular aggregation and strong intermolecular or intramolecular interactions; emission losses in solution or in the solid state along with low intensity of emission are known as aggregation-caused quenching (ACQ). [10] These types of molecules are not effectively used and have difficulties for practical application.Modern architecture molecules have brought solutions for all the drawbacks of conventional molecules. The cutting edge technology introduced by Tang and colleagues in 2001 is called aggregationinduced emission (AIE), which is not similar to the ACQ of organic luminophores. [11] AIE is a fascinated technology, purely utilized in

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Effect of increasing methoxyphenyl substitution on pyrene pyrazoline enduring green light emitting materials

Cited by 13 publications

References 65 publications

Synthesis of Piperidine‐based Derivatives as Red Emitting Lu‐minescent Materials

Synthesis of Piperidine‐based Derivatives as Red Emitting Lu‐minescent Materials

A Review on Metal Ion Sensors Derived from Chalcone Precursor

Twisted intramolecular motion arrested in aggregated state emission and the nonlinear optical properties of pyrene pyrazoline derivatives

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