Electron Push–Pull Effects in 3,9-Bis(<i>p</i>-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning

Ahn, Mina; Kim, Minji; Wee, Kyung‐Ryang

doi:10.1021/acs.joc.9b01849

Cited by 27 publications

(22 citation statements)

References 46 publications

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“…The bathochromic shift of 5 d is related to the additional push-pull effect coming from the dimethylamino substituent. [39] For compounds 6 a-b, the optimized excited state geometries are similar for both tautomers, supporting the model of proton transfer in the excited state. The enol-imine tautomer presents a calculated emission transition around 380 nm, similar to fluorophores 5 a-b, corresponding to the push-pull effect from the anisole to the pyridine, and the keto-enamine tautomer presents an additional calculated emission transition around 460 nm.…”

Section: Synthesissupporting

confidence: 60%

“…In the case of 6 b , the presence of a strong intramolecular hydrogen bond constrains the phenol ring to be close to coplanar with the pyridine ring. This strong hydrogen bond increases the electro‐withdrawing character of the pyridine, and as a consequence the 4‐phenyl ring comes closer to coplanarity, increasing the conjugation of the backbone [39] …”

Section: Resultsmentioning

confidence: 99%

“…This strong hydrogen bond increases the electro-withdrawing character of the pyridine, and as a consequence the 4-phenyl ring comes closer to coplanarity, increasing the conjugation of the backbone. [39] Scheme 1. Synthesis of the triarylpyridine fluorophores.…”

Section: Synthesismentioning

confidence: 99%

“…Those gaps are similar for 5 a-c, smaller for 5 d, and much smaller for 5 e. This could rationalize the fact that 5 a-c have similar optoelectronic properties and that 5 d present a red shift in both absorption and emission. [39] The very small gap of 5 e could explain the absence of notable emission. The HOMO-LUMO gaps of the enol-imine tautomers of 6 a-e are in the same range as the corresponding 5 a-e. On the other hand, the gaps are much smaller for the keto-enamine tautomers, and this is usually observed for such tautomerism.…”

Section: Synthesismentioning

confidence: 99%

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Unsymmetrical 2,4,6‐Triarylpyridines as Versatile Scaffolds for Deep‐Blue and Dual‐Emission Fluorophores

Fontes

Silva

et al. 2020

ChemPhotoChem

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Pyridines substituted with different aromatic groups at C-2, C-4 and C-6 were prepared following a Kröhnke synthetic route. Introducing ortho-anisole at C-2 resulted in deep blue emitters in solution, with quantum yields up to 74 %. On the other hand, when ortho-phenol was introduced, forming a strong hydrogen bond with the pyridine nitrogen, excited-state intramolecular proton transfer was witnessed by the dual emission of the fluorophores, which is sensitive to the dye environment. The phenyl ring at C-4 was used to introduce electron-donating or withdrawing groups, to fine-tune the photophysical properties of the dyes. Crystal structures of the fluorophores, together with theoretical studies using DFT/TD-DFT calculations, were used to rationalize the experimental photophysical properties of the two families of dyes. Unsymmetrical 2,4,6-triarylpyridines are therefore versatile scaffolds for the preparation of deepblue and dual emission fluorophores, and are promising building blocks for luminescent devices and sensors.

show abstract

Section: Synthesissupporting

confidence: 60%

Section: Resultsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

See 2 more Smart Citations

Unsymmetrical 2,4,6‐Triarylpyridines as Versatile Scaffolds for Deep‐Blue and Dual‐Emission Fluorophores

Fontes

Silva

et al. 2020

ChemPhotoChem

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“…The synthetic route of Y-1 and Y-2 is shown in Scheme 1. The intermediates 1 and 2 are prepared according to literatures [34][35][36][37].…”

Section: Synthesis Of Benzothiadiazole Dyesmentioning

confidence: 99%

Visible light-induced cationic photopolymerization by diphenyliodonium hexafluorophosphate and benzothiadiazole dyes

Liu

Wang

et al. 2020

Polym. Bull.

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New benzothiadiazole-based long-wavelength organic dyes (Y-1 and Y-2) were prepared for effectively sensitizing diphenyliodonium hexafluorophosphate (IOPF) to initiate the fast curing of bisphenol-A epoxy resin (E51) under visible light, avoiding traditional UV light sources that have high energy and high radiation. Y-1 and Y-2 have absorption spectra extended to more than 550 nm. By using Y-1 and Y-2 as photosensitizers for IOPF, E51 reach high epoxy conversions of 95% under light wavelength of 470-nm irradiation. IOPF and benzothiadiazole dyes present at the same time show good visible-light initiating activity. The high curing conversions are attributed to the photoelectron transfer reaction between diphenyliodonium hexafluorophosphate and benzothiadiazole dyes, based on our photochemical and electrochemical experiments. In addition, the terminated groups or of Y-1 (-F) and Y-2 (-OCH 3) have a great influence on the photopolymerization rate of the curing systems and thermal properties of E51 after cured. In addition, E51 was even polymerized about 70% in the presence of 510-nm light filter.

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Electron Push‐Pull Effects for Solution and Solid‐State Emission Control in Naphthalene 2,7‐Position‐Based Donor–Acceptor–Donor

Kim,

Nam,

Lee

et al. 2024

Asian J Org Chem

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Organic luminescent materials have garnered significant attention owing to their potential applications, particularly due to their inherent flexibility and ease of processability. Accordingly, the development of strategies that enable precise control over both intra‐ and intermolecular interactions, which directly influence their emission properties, is of paramount importance. In this study, a series of naphthalene (NAP) 2,7‐position‐based donor–acceptor–donor (D–A–D) compounds were designed and synthesized to investigate the electron push‐pull effect on intramolecular and intermolecular interactions. The energy bandgaps of the compounds were controlled by the electron push‐pull effect, resulting in red‐shifted emission within 48 nm in the order of increasing electron‐donating ability in solution state. Experimental data and theoretical calculations show that the intramolecular charge transfer (ICT) properties of D–A–D compounds are systematically controlled by electron push‐pull effects. In particular, the solid‐state emission of the compounds showed a redshift in the same order as that observed in solution. This solid‐state emission behavior is explained by the electron push‐pull effect‐dependent intermolecular interactions. Consequently, an efficient single‐molecule and multi‐molecule emission control strategy by electron push‐pull effect in NAP 2,7‐position‐based D–A–D was successfully demonstrated.

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Electron Push–Pull Effects in 3,9-Bis(p-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning

Cited by 27 publications

References 46 publications

Unsymmetrical 2,4,6‐Triarylpyridines as Versatile Scaffolds for Deep‐Blue and Dual‐Emission Fluorophores

Unsymmetrical 2,4,6‐Triarylpyridines as Versatile Scaffolds for Deep‐Blue and Dual‐Emission Fluorophores

Visible light-induced cationic photopolymerization by diphenyliodonium hexafluorophosphate and benzothiadiazole dyes

Electron Push‐Pull Effects for Solution and Solid‐State Emission Control in Naphthalene 2,7‐Position‐Based Donor–Acceptor–Donor

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