Synthesis and optical properties of the isomeric pyrimidine and carbazole derivatives: Effects of polar substituents and linking topology

Skardžiūtė, Lina; Dodonova, Jelena; Voitechovicius, A.; Jovaišaitė, Justina; Komskis, Regimantas; Voitechoviciute, Asta; Bucevičius, Jonas; Kazlauskas, Karolis; Juršėnas, Saulius; Tumkevičius, Sigitas

doi:10.1016/j.dyepig.2015.03.008

Cited by 27 publications

(15 citation statements)

References 67 publications

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“…This situation is significantly improved when carbazolyl groups are introduced into the molecular structure. In the case with a different substitution at the C2/C4 positions, the presence of the carbazolyl group at C4 results in a slightly red‐shifted emission with a higher quantum yield ( 42 and 44 vs 41 and 43 , respectively) and a longer fluorescence lifetime (1.87 and 2.27 ns vs 1.21 and 1.15 ns) . These observations are attributed to the fact that more bulky carbazole groups suppress torsional motions .…”

Section: Arylpyrimidinesmentioning

confidence: 99%

“…In the case with a different substitution at the C2/C4 positions, the presence of the carbazolyl group at C4 results in a slightly red‐shifted emission with a higher quantum yield ( 42 and 44 vs 41 and 43 , respectively) and a longer fluorescence lifetime (1.87 and 2.27 ns vs 1.21 and 1.15 ns) . These observations are attributed to the fact that more bulky carbazole groups suppress torsional motions . The emission maxima depend on the second electron‐donating para ‐substituent and this increases in the following order: OMe ( 41 , 42 ) < Ph ( 43 , 44 ) < carbazol‐9‐yl ( 45 ).…”

Section: Arylpyrimidinesmentioning

confidence: 99%

“…2,4‐Diarylpyrimidines can be obtained by Suzuki cross‐coupling reaction from commercially available 2,4‐dichloropyrimidine (Figure ) ,…”

Section: Arylpyrimidinesmentioning

confidence: 99%

“…In accordance with quantum chemical calculations, the absence of steric interaction between the pyrimidine ring and the aryl substituents at position 2 stabilizes a coplanar conformation. Whereas, the aryl substituents at position 4 are slightly out of plane, which might enhance a non‐radiative deactivation of the excited state …”

Section: Arylpyrimidinesmentioning

confidence: 99%

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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: Arylpyrimidinesmentioning

confidence: 99%

Section: Arylpyrimidinesmentioning

confidence: 99%

“…2,4‐Diarylpyrimidines can be obtained by Suzuki cross‐coupling reaction from commercially available 2,4‐dichloropyrimidine (Figure ) ,…”

Section: Arylpyrimidinesmentioning

confidence: 99%

Section: Arylpyrimidinesmentioning

confidence: 99%

See 2 more Smart Citations

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

2018

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“…Skardziute et al 67 reported the syntheses and optical properties of a series of pyrimidine/ carbazole conjugated molecules. These compounds showed strong intramolecular CT characteristics in the excited states; this was proven by solvatochromic dynamics and was supported by density functional theory (DFT) calculations.…”

Section: Pyrimidine-containing Conventional Fluorescent Blue Emittersmentioning

confidence: 99%

Recent progress of pyrimidine derivatives for high-performance organic light-emitting devices

2018

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Abstract. Pyrimidine is an electron-deficient azaaromatic compound containing two nitrogen atoms at 1, 3-positions that plays a key role as an organic semiconductor or semiconducting material. Because of the high electron-accepting property induced by C═N double bonds and due to its coordination ability, pyrimidine has been incorporated as a building block in phosphorescent emitters, fluorescent emitters, bipolar host materials, and electron transporting materials in organic light-emitting devices (OLEDs). Recently, pyrimidine-based thermally activated delayed fluorescent emitters combined with various electron donors have been developed, and their device performances were far better than those based on conventional fluorescent emitters. In this review, recent progress of pyrimidine-based OLED materials is presented and accompanied by a historical overview, current status, key issues, and outlook for the next generation of high-performance OLED materials.

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Aggregation‐Induced Enhanced Emission of a Dimethylacridan Substituted Pyrimidine Derivative

et al. 2023

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A pyrimidine chromophore bearing an acridan fragment was synthesized and its photophysical properties were studied. In solution, this compound is characterized by an important positive emission solvatochromism with a shift of 5800 cm−1 between nonpolar heptane and dichloromethane (DCM) associated with large Stokes shifts (up to 9100 cm−1 in DCM). Mono‐exponential fluorescence decays are observed in heptane whereas more complicated bi‐ or three‐exponential decays are observed in more polar solvents due to an interplay between locally excited and charge transfer excited state. Additionally, an aggregation‐induced enhanced emission process was demonstrated in THF/water mixtures. At low temperature (77 K), in a polymethylmethacrylate (PMMA) thin film, the presence of an accessible triplet state (T1) was demonstrated, which was not observed in solution. Finally, we show that it is possible to protonate the chromophore in thin film leading to panchromatic dual emission

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Synthesis and optical properties of the isomeric pyrimidine and carbazole derivatives: Effects of polar substituents and linking topology

Cited by 27 publications

References 67 publications

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

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

Recent progress of pyrimidine derivatives for high-performance organic light-emitting devices

Aggregation‐Induced Enhanced Emission of a Dimethylacridan Substituted Pyrimidine Derivative

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