Glass-forming derivatives of 2-cyano-2-(4H-pyran-4-ylidene) acetate for light-amplification systems

Zariņš, Elmārs; Siltāne, Karīna; Perveņecka, Jūlija; Vembris, Aivars; Kokars, Valdis

doi:10.1016/j.dyepig.2018.11.041

Cited by 5 publications

(4 citation statements)

References 47 publications

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“…The spectral narrowing effect was clearly seen in all samples with FWHM dropping down to 10 nm at higher pumping intensities. These threshold values are comparable to other red and deep‐red laser dyes at doping concentrations of 5 wt% or higher.…”

Section: Resultssupporting

confidence: 77%

Deep‐Red Lasing and Amplified Spontaneous Emission from Nature Inspired Bay‐Annulated Indigo Derivatives

Shukla

Wallwork

et al. 2019

Advanced Optical Materials

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While noteworthy progress has been made on organic solid‐state lasers with low amplified spontaneous emission (ASE) thresholds and high optical gains in blue and green colors, the same advancement has not been achieved for red laser dyes. This is mainly due to their low photoluminescence quantum yields (PLQYs) because of “energy bandgap law.” Here, a new family of solution‐processable organic semiconductor laser dyes based on a bay‐annulated indigo derivative (Cibalackrot) with deep‐red emission is reported. They exhibit excellent PLQYs and low ASE thresholds (9.6 µJ cm−2) with deep‐red emission when blended in a mixed host of 1,3‐bis(N‐carbazolyl)benzene (mCP) and 2‐hydroxyphenylbenzothiazole (HBT). In contrast to a single blend in mCP, the co‐blend films are found to significantly enhance the photostability by retaining 90% of initial ASE intensity even after continuous pumping with over 9000 pulses at a pump input energy twice that of the ASE threshold, which can be attributed to efficient cascade energy transfer from mCP to HBT and then to the Cibalackrot chromophore. Low lasing threshold of 6 µJ cm−2 is further achieved at 641 nm by using distributed feedback gratings. Transient absorption spectroscopy measurements indicate that the dye has extremely low yield of triplet excited‐state under optical excitation. The results show Cibalackrot derivatives to be a promising new family of organic deep‐red laser dyes.

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Section: Resultssupporting

confidence: 77%

Deep‐Red Lasing and Amplified Spontaneous Emission from Nature Inspired Bay‐Annulated Indigo Derivatives

Shukla

Wallwork

et al. 2019

Advanced Optical Materials

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“…This can be attributed to relatively higher σ em and comparable k r of HBT-Fl2 , compared to HBT-Fl1 as can be seen in Figure S13 and Table . The obtained E th values for HBT-Fl2 blend films can be compared with previously reported high-performing laser dyes emitting in the wavelength range 580–740 nm (Figure S1 in the Supporting Information). ,− Clearly, the ASE E th of 5.3 μJ/cm 2 (λ ASE = 609 nm) for HBT-Fl2 is, to the best of our knowledge, one of the lowest thresholds reported for organic laser dye with emission wavelengths >600 nm, showing the promising potential of the zwitterionic ESIPT HBT-Fl2 for laser applications. Furthermore, it is worth noting that most reported materials show efficient performance only at very low doping concentrations (1–5 wt %) due to strong intermolecular interactions forming aggregates, while HBT-Fl2 demonstrates a low threshold at 10 wt % doping as well as in neat films.…”

Section: Resultssupporting

confidence: 55%

Amplified Spontaneous Emission from Zwitterionic Excited-State Intramolecular Proton Transfer

et al. 2022

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The unique four-level photocycle characteristics of excited-state intramolecular proton transfer (ESIPT) materials enable population inversion and large spectral separation between absorption and emission through their respective enol and keto forms. This leads to minimal or no self-absorption losses, a favorable feature in acting as an optical gain medium. While conventional ESIPT materials with an enol–keto tautomerism process are widely known, zwitterionic ESIPT materials, particularly those with high photoluminescence, are scarce. Facilitated by the synthesis and characterization of a new family of 2-hydroxyphenyl benzothiazole (HBT) with fluorene substituents, HBT-Fl1 and HBT-Fl2, we herein report the first efficient zwitterionic ESIPT lasing material (HBT-Fl2). The zwitterionic ESIPT HBT-Fl2 not only shows a remarkably low solid-state amplified spontaneous emission (ASE) threshold of 5.3 μJ/cm2 with an ASE peak at 609 nm but also exhibits high ASE photostability. Coupled with its substantially large Stokes shift (≈236 nm ≈10,390 cm–1) and an extremely small overlap of excited-state absorption with ASE emission, comprehensive density functional theory (DFT) and time-dependent DFT studies reveal the zwitterionic characteristics of HBT-Fl2. In opposition to conventional ESIPT with π-delocalized tautomerism as observed in analogue HBT-Fl1 and parent HBT, HBT-Fl2 instead shows charge redistribution in the proton transfer through the fluorene conjugation. This structural motif provides a design tactic in the innovation of new zwitterionic ESIPT materials for efficient light amplification in red and longer-wavelength emission.

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“…These furnished reaction conditions were used in the synthesis of Wq-2XTr which was obtained in 49% yield. Based on the research conducted previously [12][13] it is expected that piperidine group and bulky triphenylgroup in compound Wq-2N and Wq-2XTr chemical structures would promote the solution processing ability of synthesized Alq3 complexes. Compound Wq-2NOH was successfully obtained in 82% yield according to source [9] without the addition of a catalyst.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Spectroscopic Characteristics of Ligands Based on Quinolin-8-Ol as Useful Precursors for Alq3 Type Complexes

Zariņš

Alksnis

Paulsone

et al. 2021

KEM

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In order to develop reliable methods for the synthesis of various 5-substituted-8-oxyquinoline derivatives for the preparation of Alq3-type complexes, we have improved the reaction conditions on some syntheses described in the literature, successfully synthesized new ligands based on quinolin-8-ol and characterized their chemical structures by NMR. Some of the synthesized quinolin-8-ol derivatives containing incorporated bulky triphenyl or tert-butyl groups showed blue luminescence in the solid state due to the possible aggregation induced emission enhancement (AIEE) with a maximum wavelength around 510 nm. More detailed light-emission property investigation of the mentioned bulky group containing compounds is currently underway.

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Glass-forming derivatives of 2-cyano-2-(4H-pyran-4-ylidene) acetate for light-amplification systems

Cited by 5 publications

References 47 publications

Deep‐Red Lasing and Amplified Spontaneous Emission from Nature Inspired Bay‐Annulated Indigo Derivatives

Deep‐Red Lasing and Amplified Spontaneous Emission from Nature Inspired Bay‐Annulated Indigo Derivatives

Amplified Spontaneous Emission from Zwitterionic Excited-State Intramolecular Proton Transfer

Synthesis and Spectroscopic Characteristics of Ligands Based on Quinolin-8-Ol as Useful Precursors for Alq3 Type Complexes

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