Protonable pyrimidine derivative for white light emission

Achelle, Sylvain; Rodríguez‐López, Julián; Cabon, Nolwenn; Guen, Françoise Robin‐le

doi:10.1039/c5ra21514e

Cited by 36 publications

(24 citation statements)

References 39 publications

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“…The replacement of a 1,4‐phenylene linker by either a 2,6‐naphthylene unit ( 228 vs 213 ) or a 2,7‐fluorenylene unit ( 293 vs 292 ) results in a significant bathochromic shift in the absorption and emission, as well as a dramatic increase in the quantum yield. Thin films of polystyrene doped with chromophore 228 exhibit a slightly blue shifted emission (λ em =443 nm, Φ F =0.34) when compared with CH 2 Cl 2 solution (λ em =470 nm, Φ F =0.37) . As observed in other series of pyrimidine chromophores, extension of the π‐conjugated linker to a biphenylenevinylene linker results in a red‐shifted emission ( 232 – 234 vs 215–217 , respectively).…”

Section: Arylvinylpyrimidinesmentioning

confidence: 74%

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

2018

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The extraordinary richness of push-pull molecules that incorporate pyrimidine rings as electron-withdrawing moieties in their structure is illustrated in this review. Interest in these pextended systems has increased dramatically over the last two decades due to their fluorescence properties and potential applications in sensing and as luminescent materials. As many as 422 different molecules are presented in an effort to establish structure-property relationships, which are often difficult to elucidate.[a] Dr.

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Section: Arylvinylpyrimidinesmentioning

confidence: 74%

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

2018

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“…[34][35]41 In a recent communication we described in detail the emission of methoxynaphthyl-substituted pyrimidine 1 (Chart 1) with different amounts of trifluoroacetic acid (TFA). 42 When the neutral and protonated forms were present in the appropriate ratio, intense white emission was observed both in solution and in thin films. The aim of the work described here was to study the luminescence behavior upon protonation of twelve diazine chromophores with the structural specifications required for intense emission of both their neutral and protonated forms (Chart 1).…”

Section: Introductionmentioning

confidence: 99%

Luminescence Behavior of Protonated Methoxy-Substituted Diazine Derivatives: Toward White Light Emission

et al. 2016

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White light emitting diodes (WOLEDs) are an efficient alternative to conventional lighting sources. Nevertheless, approaches to obtain WOLEDs still require complex processes that lead to high costs. In this sense, the use of a single emitting material that can take two forms of complementary emitting colors has emerged as a new strategy for the fabrication of WOLEDs. In this paper we describe the luminescent behavior upon protonation of a series of D-π-A push-pull molecules based on a methoxyphenyl or methoxynaphthyl donor unit and a diazine acceptor unit with different π-bridges. The effect of protonation on the emission properties depends on the nature of the diazine ring. The addition of trifluoroacetic acid (TFA) to pyrazine and quinoxaline derivatives led to quenching of the fluorescence whereas pyrimidine derivatives remained luminescent after protonation, which prompted a color change in the emission due to the appearance of a new red-shifted band in the spectra. These results were rationalized with the help of TD-TFT calculations. White photoluminescence could be obtained in solution by the controlled protonation of some pyrimidines, which resulted in the formation of an orange emissive acidified form. This phenomenon opens up the possibility of exploiting these materials for the fabrication of WOLEDs.

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“…An interesting way of tuning the photophysics of the molecules bearing the above mentioned π-deficient groups is through protonation, which promotes enhanced ICT as well as redshifted fluorescence spectra originated by the protonated species. [34][35][36][37][38][39][40][41][42] EET has been identified as the underlying mechanism in such protonated systems shifting the emission from the blue (emission from the non-protonated species) to the red spectral region (emission from the protonated species). 35,37,38 The above can be also exploited for the generation of white light emitters to be used in White Organic Light Emitting Diodes (WOLEDs) providing an increased interest in these donor- acceptor molecules with heterocyclic electron acceptors.…”

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confidence: 99%

Photophysical and Protonation Time Resolved Studies of Donor–Acceptor Branched Systems With Pyridine Acceptors

et al. 2018

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A comparative study of the photophysical properties of octupolar pyridyl-terminated triphenylamine molecule, with its quadrupolar and dipolar analogues by means of ambient and low temperature steady state spectroscopy and fs to ns time resolved fluorescence spectroscopy is reported. The push-pull molecules bear triphenylamine electron donating core, pyridine peripheral electron acceptors and acetylenic π-bridge. The samples were studied in solvents of varying polarity and also upon addition of small amounts of acetic acid to induce protonation of the pyridine group. All samples exhibit significant positive fluorescence solvatochromism as well as a relaxation of their excited state to a solvent relaxed Intramolecular Charge Transfer state on the ps timescale. For the octupolar compound, excited state relaxation occurs simultaneously with excitation energy hopping among the branches. The hopping time is solvent polarity controlled since it becomes slower as the polarity increases. The experimental hopping times are compared to those predicted by Förster and Fermi formulations. The samples are capable of emitting broadband light covering almost the whole visible spectrum by careful control of protonation. Energy transfer from the neutral towards the protonated species on the 1 ps timescale is revealed.

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Protonable pyrimidine derivative for white light emission

Cited by 36 publications

References 39 publications

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

Luminescence Behavior of Protonated Methoxy-Substituted Diazine Derivatives: Toward White Light Emission

Photophysical and Protonation Time Resolved Studies of Donor–Acceptor Branched Systems With Pyridine Acceptors

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