AIE and reversible mechanofluorochromism characteristics of new imidazole-based donor–π–acceptor dyes

Sharif, O.F. Al; Nhari, Laila M.; El‐Shishtawy, Reda M.; Zayed, Mohie E. M.; Asiri, Abdullah M.

doi:10.1039/d2ra01466a

Cited by 9 publications

(5 citation statements)

References 78 publications

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“…There are a few noticeable differences in the data provided in Table 3. First, the FR strength of combination mode comprised of (27,46) becomes visibly weaker in isomer 2, especially in THF. Second, THF is more effective solvent to differentiate the isomers, as parameter changes are largest between the isomers in THF.…”

Section: Resultsmentioning

confidence: 99%

“…We therefore looked more into the coupling induced by the use of different basis set and data similar to Table 3 for other basis sets are summarized in Tables 5-10. Note: From Top to bottom rows of data are for the combination band (27,45), (27,46), (36,39), and the overtone (39), respectively. *data taken from ref.…”

Section: Resultsmentioning

confidence: 99%

“…73. Note: From Top to bottom rows of data are for the combination band (27,45), (27,46), (36,39), and the overtone (39), respectively. *data taken from ref.…”

Section: Resultsmentioning

confidence: 99%

“…The parameters obtained from B3LYP/6-311++G(d,p) of isomers 1 and 2.Note: Top, middle, and bottom rows of data are for the combination band(27,45),(27,46), and the overtone(39), respectively. *data taken from ref.73.…”

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confidence: 99%

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DFT Studies of Rotational Conformers of 4-Azido-N-Phenylmalemide

Perera

Wang

2023

Preprint

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DFT calculations were performed to study the rotational conformers of 4-Azido-N-Phenylmalemide using B3LYP with 7 basis sets, 6-31G(d,p), 6-31+G(d,p), 6-31++G(d,p), 6-311G(d,p), 6-311+G(d,p), 6-311++G(d,p), and 6-311++G(df,pd). DFT studies show that the two isomers of 4-Azido-N-Phenylmalemide have the same energetics. Furthermore, the rotational barrier between the isomers is 0.17 eV in N, N-dimethylacetamide (NNDMA) and 0.15 eV in tetrahydrofuran (THF). These indicate that the isomers are present in the solvents and can be easily converted between them. The azido asymmetric stretch differs by about 1 cm-1 between the isomers in NNDMA and less than 1 cm-1 in THF. The most significant effect of rotational conformers is in the coupling strength of fermi resonances with the most impact in THF environment. Therefore, the current DFT results show that isomers of 4-Azido-N-Phenylmalemide can be mostly detected in THF by 2D IR technique. Furthermore, the results from seven basis set provide consistent conclusion on the isomers, dependence of the basis sets may be useful information to the development of functionals in DFT method and may be served as a useful tool to understand coupling of vibrational modes of complex molecules and their isomers.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…73. Note: From Top to bottom rows of data are for the combination band (27,45), (27,46), (36,39), and the overtone (39), respectively. *data taken from ref.…”

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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DFT Studies of Rotational Conformers of 4-Azido-N-Phenylmalemide

Perera

Wang

2023

Preprint

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“…2,16,[22][23][24][25][26][27][28][29][30][31] Moreover, these functional structures show excellent electron-donating ability and have been widely used as donors in the design and synthesis of various D-π-A type dyes. [32][33][34][35][36][37][38][39][40] Compared with organometallic dyes, the internal charge transfer in triphenylamine-based dye lead to a broaden UV-vis absorption spectrum, a lower HOMO energy level and a smaller HOMO-LUMO energy gap, which make these sensitizers more efficient in the application in DSSCs. Among these triphenylamine-based dyes, the styryl triphenylamines are the simple structures not only easily accessible but also efficient.…”

Section: Introductionmentioning

confidence: 99%

Tuning the HOMO Energy of the Triarylamine Molecules with Orthogonal HOMO and LUMO Using Functional Groups

Zhuang

Amaro

Testoff

et al. 2023

Preprint

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Tuning the HOMO and LUMO energy strategically of triphenylamine derivatives plays an important role towards understanding and design of high performance organic photovoltaics. To improve on the charge separation and electron transfer properties, twenty one D-pi-A organic dyes with nitrostyryl triphenylamine-based structures (NTPAs) were designed and computationally studied, in which triphenylamine, carbazole, or indoline structures were used as donor and NO2 group as acceptor. The LUMOs of these dyes are more localized at the nitrostyryl moiety with almost the same energy and the HOMOs, which are orthogonal to the LUMOs, can be conveniently tuned by changing the donor structure and using different functional groups substituted on the donor. Compared with triphenylamine molecules, carbazole molecules decrease the HOMO energy of NTPA, whereas cis N-phenylindoline structure increase the HOMO energy. In addition, the exciton sizes generated by these dyes are also tuned in a range of 7.0-12.7 A. These results show that introduction of dimethylamino group on the triphenylamine moiety greatly increases the HOMO energy and prolongs the maximum absorption wavelength as well as increases the exciton size, indicating that NTPA dyes containing strong electron donating dimethylamino group on the donor part are promising candidates as sensitizers in the dye-sensitized solar cell applications. The results of the structural and spectral properties show good correlation with the experimental results, which confirms that the DFT method employed in this work is an effective way to design organic small molecule based sensitizers.

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Hydrogen‐Bonded Cyclic Tetramer Formation of a Pyridylethynylimidazole‐Based Fluorophore

Miura,

Murai,

Ando

et al. 2024

ChemistrySelect

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Supramolecular have promising application prospects owing to their catalytic, self‐healing, and stimulus‐responsive functions. Pyridylethynylimidazole‐based supramolecular synthons with fluorescent properties have been developed. 4‐(2‐Pyridylethynyl)‐5‐arylethynyl‐1H‐imidazole derivatives 1 with different substituents at the 4‐ and 5‐positions of the imidazole skeleton were prepared using a step‐by‐step Sonogashira coupling reaction. The fluorescence maxima of phenyl‐ and methoxyphenyl‐substituted derivatives 1a and 1c were independent of solvent polarity. On the other hand, ester‐ and cyano‐substituted 1b and 1d showed bathochromically shifted fluorescence maxima in highly polar solvents. In crystals, the 4‐(2‐pyridylethynyl)‐5‐arylethynyl‐1H‐imidazole derivatives formed a supramolecular cyclic tetramer structure via two hydrogen bonds: one was between N─H in imidazole and N in pyridine, and the other was between C─H in imidazole and N in imidazole. Introducing the pyridine ring as a hydrogen bond acceptor, in addition to the imidazole ring, promoted the unique cyclic tetramer structure formation.

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AIE and reversible mechanofluorochromism characteristics of new imidazole-based donor–π–acceptor dyes

Abstract: Four new imidazole-based donor–π–acceptor 2a–2d dyes have been synthesized, and their solvatochromism, aggregation-induced emission (AIE) and mechanofluorochromic (MFC) properties were investigated.

Cited by 9 publications

References 78 publications

DFT Studies of Rotational Conformers of 4-Azido-N-Phenylmalemide

DFT Studies of Rotational Conformers of 4-Azido-N-Phenylmalemide

Tuning the HOMO Energy of the Triarylamine Molecules with Orthogonal HOMO and LUMO Using Functional Groups

Hydrogen‐Bonded Cyclic Tetramer Formation of a Pyridylethynylimidazole‐Based Fluorophore

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