Solid state and solution fine tuning of the linear and nonlinear optical properties of (2-pyrene-1-yl-vinyl)pyridine by protonation–deprotonation reactions

Cariati, Elena; Botta, Chiara; Danelli, S. G.; Forni, Alessandra; Giaretta, A.; Giovanella, Umberto; Lucenti, Elena; Marinotto, Daniele; Righetto, Stefania; Ugo, R.

doi:10.1039/c4cc05891g

Cited by 30 publications

(21 citation statements)

References 36 publications

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“…It is well known that electron‐poor heterocyclic pyridines are good end units for the “push‐pull” chromophores for non‐linear optics (NLO) and other purposes . So, it is worthy to mention that the “pull” electronic character of the pyridine moiety could be enhanced upon the coordination to the pyridine atom . The NLO responses of push–pull chromophores are strongly affected by the surrounding and large environmental effects are observed in absorption and/or emission spectra .…”

Section: Resultsmentioning

confidence: 99%

6‐Arylamino‐2,2′‐bipyridine “Push‐Pull” Fluorophores: Solvent‐Free Synthesis and Photophysical Studies

et al. 2018

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This work describes a solvent‐free approach towards “push‐pull” fluorophores based on 5‐aryl‐2,2′‐bipyridines bearing the residues of various anilines at the α‐position of the edge pyridine cycle. We have also studied the possibility of varying (het)aromatic‐substituents at C5 position of the resulted 2,2′‐bipyridines as well as the substituents in the aniline residues. The structures of products were confirmed based on the 1H and 13C NMR spectroscopic data, mass spectrometry, elemental analysis and X‐ray diffraction analysis. The photophysical features of the synthesized compounds have been investigated. The fluorescence emission of two key compounds was studied in solvents by varying polarities. It was demonstrated that an increase in the solvent polarity led to an increase in the Stokes shift. The linear dependence of the Stokes shift of the fluorophores on the increasing of the solvent nature was demonstrated by using the Lippert–Mataga plot. The fluorescence quenching response of the fluorophores towards metal cations was also demonstrated.

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Section: Resultsmentioning

confidence: 99%

6‐Arylamino‐2,2′‐bipyridine “Push‐Pull” Fluorophores: Solvent‐Free Synthesis and Photophysical Studies

et al. 2018

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“…[14] Thin films of 1 dispersed in polymethylmethacrylate (PMMA) were prepared by spin coating few drops of ad ichloromethane solution (1:PMMA = 2, 5, 8o r1 3wt%;P MMA = 10 wt %w ith respect to the solvent) on ag lass or quartz substrates. [14] Thin films of 1 dispersed in polymethylmethacrylate (PMMA) were prepared by spin coating few drops of ad ichloromethane solution (1:PMMA = 2, 5, 8o r1 3wt%;P MMA = 10 wt %w ith respect to the solvent) on ag lass or quartz substrates.…”

Section: Methodsmentioning

confidence: 99%

“…[5] Organic salts have been used to dope the emissive material in OLEDs,h owever quenching of the emission by the organic salt occurred at high doping level, giving devices with low performances. [14] The alteration of the linear and nonlinearo ptical properties of the chromophore is induced by the modulation of its internal charge-transfer due to the external stimulus (Figure 1a and S1). [4,7] To our knowledge,e ven though highly desirable in view of many advanceda pplications, the in situ color tunability of OLEDs based on as ingle emitter by an externals timulus has neverb een reported.…”

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confidence: 99%

“…[10] These fluorophores display blue monomeric and green excimer emission, according to their supramolecular organization, [11] and long lifetime of their excited states. [14] The alteration of the linear and nonlinearo ptical properties of the chromophore is induced by the modulation of its internal charge-transfer due to the external stimulus (Figure 1a and S1). [13] We recently reported the acid-triggered reversible PL and non-linear optical properties of (2-pyrene-1-yl-vinyl)pyridine, hereafter 1,b oth in solution and in the solid state upon exposure to HCl and ammonia vapors.…”

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In Situ Electroluminescence Color Tuning by Thermal Deprotonation Suitable for Thermal Sensors and Anti‐fraud Labels

et al. 2017

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A novel and versatile approach to tune photoluminescence and electroluminescence by in situ controlled thermal deprotonation is presented. This methodology, based on a single organic π-conjugated material (pyrene derivative), allows the manufacturing of organic light-emitting diode (OLED) prototypes by solution methods with controlled tunable emission ranging from the orange (protonated form of the dye) to the blue (pristine or deprotonated form). While several protonation/deprotonation cycles can be performed on thin films, for the devices only one cycle is possible so that their use as anti-fraud labels can be envisaged. OLEDs exhibit daylight visible brightness of 150 cd m and device lifetime exceeding 30 hours of continuous operation. Thanks to the simplicity of both material design and device fabrication our approach opens new perspectives in the wide field of thermal sensors for customer care or risk perception.

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“…Up to now, numerous pyrene derivatives with good fluorescence properties have been reported. For example, (2-pyrene-1-yl-vinyl)pyridine has reversible luminescence and nonlinear optical properties [7], 4-((pyren-1-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one exhibits notable aggregation induced emission (AIE) phenomena in both solution and solid state [5]. 1-Methyl benzoate-pyrene displays pure blue monomer photoluminescence and electrogenerated chemiluminescence emissions in non-aqueous media [8].…”

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confidence: 99%

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

Huang

Wang

Ren

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 24 H 15 NO, monoclinic, P2 1 /n (no. 14), a = 10.3161 ( CCDC no.: 1579090The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of material1-Pyrenecarboxaldehyde (230 mg, 1.0 mmol) and methanol (30 mL) were placed in a round-bottom flask and stirred at room temperature for 10 min. Then 4-acetylpyridine (145 mg, 1.2 mmol) and NaOH (5 mol/L, 10 mL) were added. The resulting reaction mixture was stirred at room temperature for 30 min. The mixture was extracted with CH 2 Cl 2 . The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatog- raphy (petroleum ether:ethyl acetate = 1:4) to give the title compound as a red solid (isolated yield 50%). The isolated product was crystallized from CHCl 3 to give red single crystals. Experimental detailsAll hydrogen H atoms were positioned geometrically and refined using a riding model, with d(C-H) = 0.93 Å and U iso (H) = 1.2 U eq (C). DiscussionPyrenes are considered to be excellent organic fluorophores and they are applied as environmental probes with distinct morphology and tunable emission in various micro environments due to their polarity dependent vibronic emission, high charge carrier mobility, fluorescence lifetime and chemical stability [3][4][5][6]. Up to now, numerous pyrene derivatives with good fluorescence properties have been reported. For example, (2-pyrene-1-yl-vinyl)pyridine has reversible luminescence and nonlinear optical properties [7], 4-((pyren-1-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one exhibits notable aggregation induced emission (AIE) phenomena in both solution and solid state [5]. 1-Methyl benzoate-pyrene displays pure blue monomer photoluminescence and electrogenerated chemiluminescence emissions in non-aqueous media [8]. In order to search for more pyrene-based compounds, in this paper we report a new one.There is one molecule in the asymmetric unit (cf. the figure). Bond lengths and angles are all in the expected ranges [9]. The non-H atoms of the pyrene ring and pyridine ring are nearly planar, respectively. But the pyrene unit is not coplanar

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Solid state and solution fine tuning of the linear and nonlinear optical properties of (2-pyrene-1-yl-vinyl)pyridine by protonation–deprotonation reactions

Cited by 30 publications

References 36 publications

6‐Arylamino‐2,2′‐bipyridine “Push‐Pull” Fluorophores: Solvent‐Free Synthesis and Photophysical Studies

6‐Arylamino‐2,2′‐bipyridine “Push‐Pull” Fluorophores: Solvent‐Free Synthesis and Photophysical Studies

In Situ Electroluminescence Color Tuning by Thermal Deprotonation Suitable for Thermal Sensors and Anti‐fraud Labels

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO

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Solid state and solution fine tuning of the linear and nonlinear optical properties of (2-pyrene-1-yl-vinyl)pyridine by protonation–deprotonation reactions

Cited by 30 publications

References 36 publications

6‐Arylamino‐2,2′‐bipyridine “Push‐Pull” Fluorophores: Solvent‐Free Synthesis and Photophysical Studies

6‐Arylamino‐2,2′‐bipyridine “Push‐Pull” Fluorophores: Solvent‐Free Synthesis and Photophysical Studies

In Situ Electroluminescence Color Tuning by Thermal Deprotonation Suitable for Thermal Sensors and Anti‐fraud Labels

Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO

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Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C₂₄H₁₅NO