Anthracene-containing complexes of boron difluoride. Dual luminescence, formation of excimers, and mechanochromism

Федоренко, Е. В.; Тretyakova, Galina O.; Мирочник, А. Г.; Герасименко, А. В.; Beloliptsev, A. Yu.

doi:10.1016/j.saa.2021.120114

Cited by 3 publications

(3 citation statements)

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“…[30] Geometry optimization in the ground state is performed at the MP2 level of theory. Vertical excitation energies and excitedstate properties are obtained using the multistate multireference perturbation theory XMCQDPT2 [6]/SA-CASSCF(16,14)/ (aug)-cc-pVDZ. [31] The calculations show that 5 exhibits a planar geometry in the ground state.…”

Section: Resultsmentioning

confidence: 99%

“…Simple examples of beta‐diketonates and beta‐ketoimine based dyes often exhibit low FQYs in solutions, but demonstrate high emission in the solid state (Scheme 1). [6,7] Therefore, these dyes are promising as aggregation‐induced emitters (AIE), [8] and cannot be considered as conventional fluorescent dyes. This problem can be overcome by their annulation with conjugated systems, which leads to noticeable fluorescence in solutions [9,10] .…”

Section: Introductionmentioning

confidence: 99%

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Fluorescent 2‐Hydroxy‐3‐(pyridin‐2‐yl)‐4H‐quinolizin‐4‐ones through Dimerization of Pyridineacetic Acids

Соколов¹,

Sycheva²,

Farkhutdinova

et al. 2022

Eur J Org Chem

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorescent 2‐Hydroxy‐3‐(pyridin‐2‐yl)‐4H‐quinolizin‐4‐ones through Dimerization of Pyridineacetic Acids

Соколов¹,

Sycheva²,

Farkhutdinova

et al. 2022

Eur J Org Chem

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“…Mechanofluorochromic materials, which are solid organic light-emitting materials that change their luminous color upon mechanical stimuli by crushing or grinding, have attracted attention for their applications in security inks, memory chips, and pressure sensors [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ]. Numerous organic mechanofluorochromic materials have been reported, including metal complexes [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ], anthracene derivatives [ 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 ], pyrene derivatives [ 66 , 67 , 68 , 69 , 70 ,…”

Section: Introductionmentioning

confidence: 99%

Mechanofluorochromic Properties of 1,4-Diphenylanthracene Derivatives with Hypsochromic Shift

Kannen,

Adachi,

Nishimura

et al. 2024

Molecules

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Several types of 1,4-diphenylanthracene derivatives 1–4 were prepared, and their photophysical properties were observed in the solid and solution states. Interestingly, the CN-group-substituted 1,4-diphenylanthracene derivative 2 was found to exhibit a higher fluorescence quantum yield (ϕf = 0.71) in the solid state than in the solution state, probably due to the formation of an intermolecular Ar–CN⋯H–Ar hydrogen bond and antiparallel type locked packing structure in the solid state. Furthermore, for some derivatives, an increase in the fluorescence quantum yield was observed in the PMMA film (1 wt%) over both the solid state and the solution state. More interestingly, some of the 1,4-diphenylanthracene derivatives exhibited unusual mechanofluorochromic properties with a “hypsochromic shift” in luminous color depending on the substituents of the phenyl group, and with the derivatives having CF3, OMe, CN, and two F substituents (1d–1f, 2–4) showing a significant luminous color change with a “hypsochromic shift” after grinding. However, no change in the luminous color was observed for the derivatives having H, Me, and one F substituent (1a–1c), and especially for some of the CN-substituted derivatives, a reversible luminous color change with a “hypsochromic shift” was observed, probably due to the formation of an antiparallel type packing structure. These “hypsochromic” anthracene derivatives could probably be utilized as new mechanofluorochromic materials.

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Aromatic difluoroboron β-ketoiminate complexes: effect of substituents on mechanofluorochromism and polymorphic behavior

Khrebtov,

Tretyakova,

Fedorenko

et al. 2024

Preprint

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Aromatic difluoroboron β-ketoiminate complexes (ketimBF2) are structural nitrogen-containing analogues of aromatic difluoroboron β-diketonates (diketBF2). Aggregation-induced emission (AIE) and polymorphic behavior allow ketimBF2 to exhibit mechanofluorochromic (MFC) properties. A detailed comparative study of the luminescence of a wide range of ketimBF2 with H- and CH3-substituents of nitrogen atom and diketBF2 with various substituents of the chelate ring (methyl, phenyl, toluoyl, anisoyl, biphenyl, naphthyl, anthracyl) in the solid state was carried out. As a result, regularities of the influence of substituents on the luminescent and MFC properties for 21 dyes have been established.

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Anthracene-containing complexes of boron difluoride. Dual luminescence, formation of excimers, and mechanochromism

Cited by 3 publications

References 50 publications

Fluorescent 2‐Hydroxy‐3‐(pyridin‐2‐yl)‐4H‐quinolizin‐4‐ones through Dimerization of Pyridineacetic Acids

Fluorescent 2‐Hydroxy‐3‐(pyridin‐2‐yl)‐4H‐quinolizin‐4‐ones through Dimerization of Pyridineacetic Acids

Mechanofluorochromic Properties of 1,4-Diphenylanthracene Derivatives with Hypsochromic Shift

Aromatic difluoroboron β-ketoiminate complexes: effect of substituents on mechanofluorochromism and polymorphic behavior

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