Review
Chemistry, Multidisciplinary
Tomas Opsomer, Wim Dehaen
Summary: This article provides an overview of the latest developments in metal-free synthesis of non-benzo-fused N-functionalized and NH-1,2,3-triazoles, including oxidative and eliminative azide-dipolarophile cycloadditions, diazo transfer reactions, and N-tosylhydrazone-mediated syntheses. These newly developed methods have significantly contributed to the field of 1,2,3-triazole synthesis by exploring novel reactions and utilizing existing methodologies for structural variation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Satish V. V. Akolkar, Mubarak H. H. Shaikh, Mininath K. K. Bhalmode, Prabhakar U. U. Pawar, Jaiprakash N. N. Sangshetti, Manoj G. G. Damale, Bapurao B. B. Shingate
Summary: A small library of 1,2,3-triazole derivatives derived from naphthols has been efficiently synthesized through the click chemistry approach for the search of new active molecules. The synthesized compounds were evaluated for their antifungal, antioxidant, and antitubercular activities. Furthermore, a molecular docking study was conducted to understand the binding affinity and interactions between the enzyme and the synthesized derivatives, revealing a significant correlation between the binding score and biological activity of these compounds. The results suggest that the 1,2,3-triazole derivatives may serve as potential candidates for the development of novel therapeutic agents.
RESEARCH ON CHEMICAL INTERMEDIATES
(2023)
Article
Chemistry, Organic
Zhenhua Liu, Huimin Chen, Xingxing Gan, Lianxiao Wang, Ping Lin, Jiayi Li, Xiuxiu Huang, Rongbiao Tian, Xuan Liu, Wen Gao, Bo Tang
Summary: A tandem 2-azidoallylation/click cycloaddition reaction has been demonstrated to efficiently construct novel multifunctional hepta-1,6-dienes with quaternary/tertiary carbon centers and a bis-1,2,3-triazole scaffold.
ORGANIC CHEMISTRY FRONTIERS
Article
Chemistry, Multidisciplinary
Wiebke Haselbach, Jeremy M. Kaminski, Laura N. Kloeters, Thomas J. J. Mueller, Oliver Weingart, Christel M. Marian, Peter Gilch, Barbara E. Nogueira de Faria
Summary: The emitters for TADF-based OLEDs need to have small S-1-T-1 energy gaps and fast ISC transitions. Vibronic mixing with higher excited states S-n and T-n can mediate these transitions. By using time-resolved NIR spectroscopy, it is demonstrated that the energetically located higher states can be found in a prototypical TADF emitter consisting of a triarylamine and a dicyanobenzene moiety (TAA-DCN).
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Fabio Wilbert, Thomas J. J. Muller
Summary: One-pot syntheses of 3,3-diarylallylidene indolinones were achieved by pseudo-four-and pseudo-five-component reactions. The title compounds, which are a mixture of E/Z-configured isomers, were assessed for their photophysical characteristics using absorption and solid-state emission spectroscopy. The fluorescence of 3,3-diarylallylidene indolinones in the solid state was observed regardless of their configuration, but only when electron-withdrawing and weakly electron-releasing remote p-phenyl substituted dyes were present with concomitant Boc substitution of the lactam moiety. DFT and TD-DFT calculations were used to reproduce and rationalize the electronic structure of the longest wavelength absorption and emission bands.
Review
Chemistry, Physical
Marco Kruppa, Thomas J. J. Mueller
Summary: The Masuda borylation-Suzuki coupling (MBSC) sequence enables the direct formation of (hetero)biaryls from readily available (hetero)aryl halides under mild conditions, providing access to diverse symmetric and asymmetrically substituted scaffolds. This review summarizes the development and improvements of the MBSC sequence over the past two decades.
Article
Chemistry, Physical
Julia Wiefermann, Jeremy M. M. Kaminski, Elisabeth Pankert, Dirk Hertel, Klaus Meerholz, Christel M. M. Marian, Thomas J. J. Mueller
Summary: In this study, we investigated the optoelectronic properties of a previously reported blue emitter. The analysis of the emission spectra in solvents with different polarities indicated charge transfer contributions to the first singlet excited state, S-1. Quantum chemical calculations revealed a balanced local excitation and charge transfer character of the S-1 state, and suggested the presence of a local excitation triplet state, T-2, in its energy vicinity. Finally, organic light emitting diodes exhibited blue emission at 451 nm with an external quantum efficiency of 2% and an internal quantum efficiency of approximately 10%.
Article
Chemistry, Multidisciplinary
Paulina H. Marek-Urban, Karolina A. Urbanowicz, Karolina Wrochna, Piotr Pander, Agata Blacha-Grzechnik, Simone T. Hauer, Henning R. V. Berens, Krzysztof Wozniak, Thomas J. J. Mueller, Krzysztof Durka
Summary: A synthetic approach to two regioisomeric pi-electron extended [1,4]thiaborins annulated with two benzothiophene units has been developed. The obtained boracycles exhibit different electronic properties reflected in their aromatic characters, boron Lewis acidity, and UV-vis spectroscopic behavior. The spiro thiaborin-BODIPY complexes show excellent photocatalytic performance as singlet oxygen photosensitizers with high singlet oxygen quantum yields and full conversion of organic substrates.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Laura N. Kloeters, Jan A. Meissner, Lysander Presser, Markus Suta, Jan Meisner, Thomas J. J. Mueller
Summary: The bromine-lithium exchange-borylation-Suzuki sequence efficiently synthesizes phenothiazine-terephthalonitrile donor-acceptor dyads and triads with high yields. These compounds are ligated in p-position to the phenothiazine nitrogen atom and have either direct or arylene bridge linkage to the acceptor. The intra-configuration of the tricycle is locked by p-anisyl N-substituents. The compounds show similar optical properties and TADF behavior in various states.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Julia Wiefermann, Thomas J. J. Mueller
Summary: A series of triphenylamine-pyridine chromophores were synthesized by bromine-lithium exchange borylation-Suzuki sequence with moderate to good yields. The electronic properties of these compounds were studied using absorption and emission spectroscopy, as well as quantum chemical calculations. The compounds exhibited deep- and sky-blue emission in solution and in the solid state. Hammett correlations were used to investigate the structure-property relationship. The compounds showed clear color impressions with small FWHM values. Additionally, they displayed positive solvatochromism and acidochromism, and one compound exhibited dual emission possibly due to a TICT state.
Editorial Material
Chemistry, Physical
J. Wiefermann, J. M. Kaminski, E. Pankert, D. Hertel, K. Meerholz, C. M. Marian, T. J. J. Mueller
Summary: In this study, the optoelectronic properties of a previously reported blue emitter were thoroughly investigated. Lippert-Mataga analysis of the emission spectra in different solvents revealed charge transfer contributions to the first singlet excited state, S-1. Quantum chemical calculations showed a balanced local excitation and charge transfer character of the S-1 state, and also suggested the presence of a nearby local excitation triplet state, T-2. Finally, organic light emitting diodes (OLED) demonstrated blue emission at 451 nm with an external quantum efficiency of 2% and an internal quantum efficiency of around 10%.
Article
Chemistry, Organic
Nadia Ledermann, Alae-Eddine Moubsit, Thomas J. J. Mueller
Summary: A library of 19 differently substituted 3-iodoindoles has been generated by a consecutive four-component reaction, which provides a concise one-pot synthesis of valuable substrates for Suzuki arylations. Some of the synthesized compounds exhibit good reaction activity and emission properties in the Suzuki arylations.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lukas Biesen, Yannic Hartmann, Thomas J. J. Mueller
Summary: Symmetric and unsymmetric diaroyl-S,N-ketene acetals can be easily synthesized in good yields by utilizing the nucleophilic character of the methine position. The resulting aroyl compounds exhibit tunable emission properties and increased stability of luminescent aggregates.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Lukas Biesen, Thomas J. J. Muller
Summary: Aroyl-S,N-ketene acetals are a unique class of heterocyclic dyes with tunable solid-state emission and aggregation-induced emission properties. They can be synthesized using various methods and can be further expanded into systems with multiple chromophores.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Kseniya A. Alekseeva, Maryana A. Nadirova, Vladimir P. Zaytsev, Evgeniya V. Nikitina, Mikhail S. Grigoriev, Anton P. Novikov, Irina A. Kolesnik, Bernhard Mayer, Thomas J. J. Mueller, Fedor I. Zubkov
Summary: Diversely substituted, partially saturated benzo-[f]-isoindole-4-carboxylic acids were synthesized through a new three-component reaction. The reaction showed high regio- and stereoselectivity, resulting in the formation of a chiral center and a diastereoisomer.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Lukas Biesen, Thomas J. J. Mueller
Summary: Donor-substituted aroyl-S,N-ketene acetals were rapidly synthesized by nucleophilic attack and decarbonylation, followed by addition-elimination reaction. These compounds exhibited intensive solid-state emission and pronounced aggregation-induced emission (AIE) characteristics with high quantum yields. By changing the base, enlarged aroyl-S,N-ketene acetal bi- and trichromophores were easily accessible.
Article
Materials Science, Multidisciplinary
Dietrich Pueschel, Julia Wiefermann, Simon Hede, Tobias Heinen, Leo Pfeifer, Oliver Weingart, Markus Suta, Thomas J. J. Mueller, Christoph Janiak
Summary: This study presents and compares the photoluminescence properties of compounds mBN, BPN, and pBN. While pBN exhibits thermally activated delayed fluorescence (TADF) properties, mBN shows weak TADF and BPN functions as a conventional fluorescent emitter. The through-space overlap between phenazinediyl and benzonitrile units is found to be effective only in pBN. The emission of these compounds in solution is weak, with the strongest intensity observed in toluene.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Lukas Biesen, Thomas J. J. Mueller
Summary: Etherified aroyl-S,N-ketene acetals can be easily synthesized via a unique one-pot addition-elimination-Williamson etherification sequence. While the chromophore remains the same, derivatives exhibit significant color tuning in solid-state emission and AIE characteristics, with a hydroxy-methyl derivative serving as an easily accessible mono-molecular aggregation-induced white-light emitter.
