Adamantyl side groups boosting the efficiency and thermal stability of organic solid-state fluorescent dyes

Krajčovič, Jozef; Коваленко, А. В.; Heinrichová, Patricie; Vala, Martin; Weiter, Martin

doi:10.1016/j.jlumin.2016.02.019

Cited by 14 publications

(6 citation statements)

References 29 publications

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“…This can be attributed to a higher degree of self-organization that is common in adamantyl compounds. 39,40 Where: λ max -wavelength at the emission maximum, FWHM -full width at half maximum of the emission peak; E g -optical bandgap.…”

Section: Methodsmentioning

confidence: 99%

Proteinogenic Amino Acid Assisted Preparation of Highly Luminescent Hybrid Perovskite Nanoparticles

Procházková

Demchyshyn

Yumusak

et al. 2019

ACS Appl. Nano Mater.

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Versatile approaches to nanoparticle synthesis offer unprecedented opportunities for the development of optoelectronics, photonics, as well as bio sciences. With the current advancement of hybrid organic-inorganic metal halide perovskites, the next step is to expand their field of applications via utilization of functional and modifiable ligand chemistry. Here, we present a ligand assisted reprecipitation approach for highly luminescent perovskite nanoparticle synthesis using for the first time L-lysine and L-arginine for surface passivation. These nanoparticles exhibit emission within a narrow bandwidth of the visible spectrum and photoluminescence quantum yield close to 100%. Additionally, preferential ligand orientation is achieved via amino acids α-amino group blocking which results in blueshifted emission as well as smaller and more uniform particle size. These experimental results demonstrate the effectiveness of naturally occurring proteinogenic amino acids as surface ligands and offer possibilities for versatile modification of perovskite nanoparticle properties via well-studied amino acid chemistry.

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Section: Methodsmentioning

confidence: 99%

Proteinogenic Amino Acid Assisted Preparation of Highly Luminescent Hybrid Perovskite Nanoparticles

Procházková

Demchyshyn

Yumusak

et al. 2019

ACS Appl. Nano Mater.

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“…Comparing the effect of the alkyl substitution, the thermal stability of the butyl-substituted flavins (compounds 1, 3, 5, and 7) is lower compared to the ethyl-adamantyl-substituted counterparts (compounds 2, 4, 6, and 8). We assume that this observation can be reasoned by the effect of bulky rigid ethyl-adamantyl groups that can contribute to thermal stability by stronger intermolecular Van der Waals interactions in the solid state compared to short linear butyl groups at both the higher decomposition temperatures and higher melting points [46,47]. The contribution of ethyl-adamantyl substitution is even more remarkable when comparing with the decomposition temperatures of the unsubstituted flavins with prevalent strong intermolecular H-bonding.…”

Section: Thermal Propertiesmentioning

confidence: 96%

“…Furthermore, the quality of the alkyl substituent can significantly alter other physico-chemical properties like thermal stability and molecular organization in the solid state [45]. Thus, we have prepared the series of 8 flavin derivatives with progressively expanded π-conjugated systems substituted with either a short linear butyl group or a bulky ethyl-adamantyl group in analogy to our previous work [46]. For instance, introduction of bulky ethyl-adamantyl substituents to para-bis(2-thienyl)phenylene trimers induced the formation of highly organized crystal structures due to hydrogen bonding between thienyl and adamantyl and molecular pairing of ethyl-adamantyl side groups [46].…”

Section: Introductionmentioning

confidence: 99%

“…Thus, we have prepared the series of 8 flavin derivatives with progressively expanded π-conjugated systems substituted with either a short linear butyl group or a bulky ethyl-adamantyl group in analogy to our previous work [46]. For instance, introduction of bulky ethyl-adamantyl substituents to para-bis(2-thienyl)phenylene trimers induced the formation of highly organized crystal structures due to hydrogen bonding between thienyl and adamantyl and molecular pairing of ethyl-adamantyl side groups [46]. Hence, a significant increase of the melting point of the material and its fluorescent quantum yield was observed compared to the methyl-substituted trimer.…”

Section: Introductionmentioning

confidence: 99%

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Tunable Properties of Nature-Inspired N,N′-Alkylated Riboflavin Semiconductors

et al. 2020

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A series of novel soluble nature-inspired flavin derivatives substituted with short butyl and bulky ethyl-adamantyl alkyl groups was prepared via simple and straightforward synthetic approach with moderate to good yields. The comprehensive characterization of the materials, to assess their application potential, has demonstrated that the modification of the conjugated flavin core enables delicate tuning of the absorption and emission properties, optical bandgap, frontier molecular orbital energies, melting points, and thermal stability. Moreover, the thin films prepared thereof exhibit smooth and homogeneous morphology with generally high stability over time.

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“…At the same time, the solubility and processability of these systems remain preserved. [38,39] In the present work, we report the synthesis, experimental and theoretical study of the novel four adamantane-bearing dyes based on the linear trans-QA and trans-EPI cores (Figures 1 and 2). The partial aims of this study are: (1) to present the effective synthetical route of the studied molecules;…”

Section: Introductionmentioning

confidence: 99%

Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

et al. 2021

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The synthesis, experimental and theoretical study of the novel air-stable four adamantane-bearing dyes based on the transepindolidione (EPI) and trans-quinacridone (QA) cores are presented. Compared to the parent EPI and QA, the methyl-/ ethyladamantyl substitution ensures that their structural stability in crystals is preserved due to the self-organizing properties of adamantyl groups. The investigated materials are solutionprocessable in common organic solvents and possess excellent thermal stability. The very good solubility was achieved by a one-step short and easy synthesis, which resulted in moderate yields of a new family of synthesized dyes. The ethyladamantyl EPI derivative (3) exhibits a unique rise in thermal stability reaching 412 °C. The resulting electrochemical band gap carried out on thin-film evaporated on ITO-coated glass electrodes was in the range of 2.4-2.5 eV. The experimental HOMO energies range from À 6.2 to À 6.0 eV, and LUMO energies lay between À 3.7 and À 3.5 eV. The prepared compounds are characterized by strong fluorescence in solutions and in powder, suggesting a decrease in the extent of non-radiative relaxation processes.

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Adamantyl side groups boosting the efficiency and thermal stability of organic solid-state fluorescent dyes

Cited by 14 publications

References 29 publications

Proteinogenic Amino Acid Assisted Preparation of Highly Luminescent Hybrid Perovskite Nanoparticles

Proteinogenic Amino Acid Assisted Preparation of Highly Luminescent Hybrid Perovskite Nanoparticles

Tunable Properties of Nature-Inspired N,N′-Alkylated Riboflavin Semiconductors

Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

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